Gobbler Hill, circa 1858 with an addition built in 1989, sits like a jewel atop one of the highest points in Kent County. Listed on the National Historic Registry, the transitional architecture is an excellent example of late Greek Revival to early Italianate. The property consists of four parcels totaling over 65 acres. Wildlife abounds on the fields of native prairie grasses, wild flowers, woods, approximately 20 tilled acres and a large pond. Impeccable attention was payed to maintaining the historic character of both the interior and exterior. From the Lincrusta wall covering, 19th century faux wood finishing, plaster medallions, white and sugar pine wood floors and crown molding on the 11 ft. ceilings to the monumental copper roof, the thoughtful restoration is stunning. The newer addition beautifully blends into the original section adding modern conveniences and natural light. The library boasts black walnut bookshelves constructed by a local craftsman. Well maintained grounds offer gardens, mature trees, a classic poured concrete in ground pool with inlaid tile and stunning views. This unique, lovingly restored piece of Kent County history is now looking for a new steward to guide it into its next chapter.

This architecturally charming waterfront home sits on 5.6-acres of well-elevated land that offers an exceptional secluded setting and panoramic, wide views of Broad Creek. Located just minutes from Historic St. Michaels, this lovely home was thoughtfully expanded by the Easton architectural firm, Atelier 11 in a way that honors its distinctive New England “Bow House” architectural style while updating the interior with high quality finishes and a thoughtful, functional floor plan. The first-floor waterside primary bedroom suite includes a library/office, a custom built-in wood paneled wardrobe/dresser wall and primary bathroom with a large glass-enclosed walk-in shower. The Laundry is conveniently located in an adjacent closet. The exceptional chef’s kitchen features a six-burner Wolf stove, a wood paneled Subzero refrigerator and Miele dishwasher. The granite counters offer plenty of prep space and the quality Mauser brand white shaker-style cabinets are quite beautiful. The large center island provides bar seating ideal for an entertaining environment. The adjacent family room offers a wall of windows to take in the exceptional water views and a Rumford brick fireplace with hewn walnut beam mantle that creates a cozy ambiance. There is a second woodburning fireplace in the adjacent den that features a wood planked beamed ceiling and built-in media cabinet. Another full bath on this level is located off the mud room that leads to the waterside deck. A separate dining room is adjacent to the entry foyer. The second level features three charming guest bedrooms and bath with soaking tub and enclosed shower. The tasteful interior features gorgeous wide-plank heart pine floors throughout the entire home, natural wood paneled doors and moldings. A detached three-car garage offers ample storage and there are two storage sheds, a fenced vegetable garden and a freshwater pond with a fountain/aerator. A partial basement and attics above the house and garage provide additional storage space. With 200 feet of riprapped shoreline, the property offers a recently built 6’ wide private dock with water, electric and 3’+ of MLW depth that is perfect for boating enthusiasts and waterfront living. The expansive grounds also feature a beautiful 20’ x 40’ waterside pool and an Ipe-wood deck where you can relax while enjoying the breathtaking, panoramic views of Broad Creek and the visiting Osprey and Bald Eagles. Come experience this enchanting property and serene setting that is just six miles from quaint Saint Michaels and its wonderful restaurants, shopping and amenities. ** Enjoy the virtual tour and floor plan by clicking on the movie camera icon!

Exquisite Waterfront Estate in Neavitt, Maryland just minutes from historic St. Michaels.Welcome to a rare opportunity to own a truly exceptional waterfront estate in the heart of Maryland’s Eastern Shore. Nestled on over 14 pristine acres, this magnificent property boasts 7 spacious bedrooms, 5 full bathrooms, and 2 powder rooms, offering luxurious comfort for both everyday living and grand-scale entertaining.Custom-built to embrace the natural beauty of its surroundings, the home is perfectly positioned along a serene stretch of the Choptank River with expansive water views from nearly every room toward the Chesapeake Bay. Enjoy over 600 plus feet of private shoreline, complete with a dock ideal for boating, crabbing, or simply watching the sunset.The residence features over 4,000 square feet of elegant living space, highlighted by high ceilings, oversized windows, and an open-concept layout that seamlessly blends classic Eastern Shore charm with modern sophistication. The main level includes a gourmet kitchen, multiple entertaining areas, and a generously sized primary suite with spa-like bath and private terrace.Enjoy an inground pool, multiple gathering patios, and vast lawns that invite relaxation or recreation. Whether you're seeking a private retreat, a family compound, or a waterfront lifestyle, this remarkable estate checks every box.To help visualize this home’s floorplan and to highlight its potential, virtual furnishings may have been added to photos found in this listing.

Comfort. Nature. Luxury. All are expressed in this Contemporary waterfront home on Southeast Creek. Listen to Ospreys from your screened porch or private second floor balcony. Cool off in the pool or practice yoga in the poolside studio space. Friends from far away can come use your detached guest cottage as a tranquil retreat. Walk down your dock and go sailing with easy access to the Chester River and beyond. Gather with the ones you care about most on the central open floor plan on the main floor. Upstairs has everything you need to decompress and take in the fine Eastern Shore lifestyle. The home is less than 15 minutes from Historic Downtown Chestertown by boat or car and less than 2 hours from Washington D.C., Philadelphia, or Baltimore.

A Rare Waterview Masterpiece Designed for the Ultimate Boating Lifestyle. Set on 1.376 acres with breathtaking water views and unforgettable sunsets, this one-of-a-kind contemporary residence delivers luxury, functionality, and resort-style living at every turn. Thoughtfully designed with the boater in mind, this exceptional home offers expansive entertaining spaces, refined finishes, and outstanding access to boating amenities. The main level showcases a dramatic living room with gas fireplace and sweeping water views, a dining room opening to the rear deck, and a stunning gourmet kitchen featuring quartzite countertops, a grand center island, Wolf 5-burner gas stove, steam oven, convection oven, butler’s pantry, and an additional pantry/storage area with refrigerator. A screened-in porch just off the kitchen creates the perfect space for relaxed water view living. Also on this level are a hall bath, office or sitting room, main-level laundry, and a luxurious primary ensuite with small deck with stunning views, double vanities, jetted tub, and a separate shower and toilet area. The second level is ideal for hosting, offering three bedrooms with 2 full baths, plus two additional sleeping areas thoughtfully designed for guests. The fully finished lower level continues the luxury with a gym, room of choice office/bedroom with full bath, additional laundry hookup, spa-like bathroom with double vanities and an oversized shower, and a rear entry perfectly suited for coming in off the water. Outdoor living is nothing short of spectacular, featuring a professionally landscaped rear patio with water feature, firepit, garden irrigation, and automatic timers. A rear garage and workshop provide ample space for water toys, gear, and golf carts. Additional highlights include a deeded boat slip with two boat lifts, 90-amp electric vehicle charger, whole-house humidifier, three-zoned HVAC, Pella windows, architectural roof (2024), automatic water shutoff system (Flow Logic), and all appliances included. An exclusive opportunity to acquire the adjacent 1.245-acre parcel, offered separately, featuring a deeded boat slip and lift, with right of first refusal extended to the purchaser. This extraordinary property offers a rare blend of luxury, privacy, and elevated water view living. Truly one of a kind—schedule your private showing today.

PANORAMIC WATERVIEWS!!!! Breathtaking Panoramic Views – Renovated Waterfront HomeExperience the beauty of waterfront living in this meticulously maintained, renovated (2024) home in Earleville, offering over 3,500 sq. ft. of living space. Designed to capture unparalleled panoramic views from every room in the rear of the home, this 3-bedroom, 2.5-bath home features an open floor plan.Step inside and be captivated by the breathtaking water views. The spacious living room boasts a floor-to-ceiling stone wall with an electric fireplace, seamlessly flowing into the stunning new kitchen with quartz countertops, brand-new appliances, a coffee bar, and a dry bar—perfect for entertaining. A sunroom and dining area provide the ideal setting to take in the serene surroundings, while custom blinds throughout the home enhance privacy and style. The main level also includes a luxurious owner’s suite and an additional bedroom or office space, both with spectacular water views.A beautiful open staircase leads to the bright and spacious lower level, where a large family room with another floor-to-ceiling stone wall featuring an electric fireplace awaits. This level also features two generously sized bedrooms, a kitchenette, and direct access to the covered lower deck, offering even more stunning waterfront views. The layout makes this space ideal for guests or an in-law suite.Extensive updates completed in 2024 include fresh interior and exterior paint, new landscaping, gutter replacement, two new HVAC systems, and brand-new kitchens and baths with high-end finishes. Outdoor living is enhanced with a spacious main-level deck featuring a retractable awning, providing comfort and shade, while the covered lower deck offers another perfect space to relax and enjoy the waterfront setting. The expansive lot offers plenty of room for an inground pool, making it ideal for entertaining and outdoor enjoyment.Additional features of this exceptional home include custom blinds, central vacuum, a 3-car garage, a deeded boat slip with lift, and private beach access. Don’t miss this rare opportunity to own a turnkey waterfront retreat where luxury meets tranquility!

Luxury Smart Home, High-End Upgrades & Off-Grid Solar. Prime Location with Waterviews and Water Access!Nestled on a 2.4-acre lot in the scenic Ingleton community, this custom-built smart homeoffers breathtaking water views and shared waterfront access, perfect for kayaking,paddleboarding, or simply enjoying the tranquil setting. Ideally located between Easton andSt. Michaels, you get the perfect balance of privacy and convenience.Smart, Sustainable, and Built for Comfort:This modern, high-tech home is designed for energy efficiency, luxury, and security.Featuring off-grid solar panels on the shed and a dual Eco-Flow in-house generator setup(Batteries not included), You will enjoy peace of mind during outages.With 3,500+ sq. ft. of finished space plus an additional 1,400+ sq. ft. of unfinished potential,this home offers room to grow and customize.Gourmet Kitchen with High-End Appliances, a dream for home chefs, boasts:✔ Viking stainless steel appliances, including a six-burner gas range with a Miele hood✔ Pot filler for added convenience✔ Quartz countertops and two functional center islands✔ Walk-in pantry for ample storage✔ Instant hot water faucet for quick meal prep✔ USB-C outlets for modern charging needsPrivate Suites & Expansive Living Spaces:✔ First-floor primary suite with a sitting area, dual walk-in closets, and spa-like en-suitebath featuring a jetted tub, separate shower, and dual vanities✔ First-floor in-law suite with a living area, kitchenette, large full bath, and direct access toA brand-new screened porch overlooking the backyard✔ Upstairs features a large bedroom, full bath, and a versatile bonus/game roomSmart Technology & Modern Upgrade:✔ 1GB wired Ethernet to every room + pre-wired connectivity to unfinished spaces✔ pre-wired outdoor security system, including shed solar-powered cameras and woodsnear the cornfield embedded with security wiring✔ New outdoor smart lighting system (including mailbox and vertical garage lights)✔ Built-in smart speaker system throughout the home✔ Upstairs 7.2 surround sound system for an immersive entertainment experience✔ Three Ecobee Smart Thermostats for energy-efficient climate control✔ Eufy Smart Security Door Locks on bedroom and garage side doorsBrand-New Mudroom & High-Performance Laundry:✔ Brand-new mudroom built off the garage for extra storage and easy entry✔ New Speed Queen dryer & Maytag washer✔ Samsung refrigerator in the garage for additional cold storage✔ GE refrigerator in the in-law suite for added convenienceUltimate Garage Setup for Car Enthusiasts:✔ Side-mount garage door openers allow space for up to six cars (lifts not included)✔ Utility sink for convenienceAdditional Highlights:✔ Finished crawl space with two new sump pumps✔ Recently sealed driveway (2024)✔ Brand-new tankless water heater (installed 3 months ago)✔ Bidets installed in bathrooms✔ Added landscaping in the rear and side of the home✔ 2023-2024 dead trees removed from property✔ All fans, lights, and blinds are brand new and were replaced in 2022✔ Brand new outdoor playsetThis one-of-a-kind smart home offers the perfect mix of luxury, energy efficiency, and state-of-the-art technology. Don’t miss this rare opportunity to own a high-tech, water viewretreat with modern upgrades and security features already in place!Schedule your private showing today!

One of the stand-out North Water Street waterfront homes in Historic Chestertown that has raised children, hosted town development meetings, entertained many, and most recently provided the perfect escape for a loving three-generation family. The house is old bones with refreshed skin in many parts of this three-story traditional Four Square and full, multi-room basement. What distinguishes this offering from other river side properties is its' entire width of house sunroom and large adjoining deck overlooking a Unity Landscaping designed garden, well maintained and equipped dock, and the beautiful Chester River.

This Waterfront Contemporary home is nestled on a bluff with sweeping views of Still Pond Creek. The property checks all of the boxes for your retreat including a well maintained deck, screened river room for crab feasts, private sandy beach and dock with several boat lifts. The living room has a cathedral ceiling, wood burning fireplace, and glass sliders leading you to the deck with incredible views of nature and wildlife. One of the 3 main floor bedrooms, the primary suite has an ensuite bathroom, walk-in closet, and full length windows to celebrate the property's connection with the water. On the lower level you will find another bedroom, den, workshop, and garage. Upgrades include New Heating and Cooling (2024&2025), New Roof (2022), Garage Door (2024), Plumbing and Electrical Updates (2022), Generator, Rinnai Tankless hot water heater, and Reverse Osmosis water treatment. Still Pond Creek provides direct access to the open waters of the Chesapeake Bay for prime boating opportunities however is a protected tributary making it great for water sports. The property is located in the rolling farmlands of Worton, only 15 minutes from the shops, restaurants, and galleries of downtown historic Chestertown. Philadelphia, Washington D.C., and Baltimore are all less than a 2 hour drive making this perfect for a weekend getaway or year round residence.

***Mortgage savings may be available for buyers of this listing***Waterfront Paradise on Madison Bay – 1312 Taylors Island Rd, Madison, MD Discover an extraordinary waterfront retreat set on nearly 10 acres with over 300 feet of protected shoreline on scenic Madison Bay. This fully renovated 3BR/3BA Cape Cod offers unmatched privacy, sweeping lawns, and panoramic water views—creating the ultimate Eastern Shore sanctuary with breathtaking sunsets and an ever-changing big sky. From the moment you travel down the private drive, you're immersed in a park-like setting rich with natural beauty. A true haven for nature lovers, the property offers front-row views of soaring bald eagles, graceful blue herons, playful terns, migrating geese, and countless other birds—each season bringing a new spectacle under the vast, open sky. The home’s main level has been thoughtfully redesigned with an open-concept layout that highlights the stunning waterfront vistas. The spacious Great Room features wide-plank flooring, abundant natural light, a cozy gas fireplace, and flows seamlessly into a screened-in porch with a paneled ceiling, new metal roof, and dual ceiling fans. From there, step onto the expansive deck—perfect for outdoor dining, entertaining, or simply soaking up the peaceful surroundings. The chef’s kitchen is a showpiece, featuring modern white cabinetry, quartzite countertops, stainless steel appliances, a deep sink with dual faucets, large island, and wall rack for cookware. The adjacent dining area offers unobstructed water views through new glass doors and includes custom lighted glass cabinetry. A large walk-in pantry includes an additional deep sink, tall storage for appliances and pantry goods, and connects to a mudroom with private entry, wine fridge, custom bench, hooks, and shelving. Also on the main level is a stylish full bath and a versatile library/den that can serve as a fourth bedroom or home office. Upstairs, you’ll find even more spectacular views. Walls of glass in the renovated primary suite frame the water and sky, creating a light-filled retreat that feels as if you’re floating above the bay. The suite features vaulted ceilings, lighted fans, walk-in closet with built-ins and glass shelving, and a spa-like bath with custom tile, quartz countertops, oversized shower with dual rain heads, large niche, Toto toilet, and picture window. A spacious secondary bedroom shares a fully renovated hall bath. The laundry has been relocated to the second floor for convenience and includes a full-size stacked washer/dryer and storage. An additional room offers flexible space for hobbies or storage and overlooks the expansive front lawn. The home’s private cove provides peace and quiet, undisturbed by boats—perfect for birdwatching, reading, or entertaining. The manicured grounds feature raised garden beds, meticulous landscaping, a fully fenced front yard, and three large flagpoles. An oversized two-car garage and large parking pad offer ample space for multiple vehicles. Located just a short drive to downtown Cambridge, enjoy easy access to dining, shopping, marinas, the arts, and Chesapeake Bay fishing. Whether you’re watching eagles soar in your big sky, enjoying sunset dinners on the deck, or simply savoring the sounds of the water, this one-of-a-kind property invites you to live fully immersed in nature. 1312 Taylors Island Rd is more than a home—it’s a waterfront lifestyle.

Located in the heart of St. Michaels' historic district, this adorable cottage has a rare zoning that allows for short term vacation rental, and it has been a very successful one. The current owner has great reviews and reports revenues of $65,000 in 2025. There is excellent bedroom separation, with one bedroom on the first floor in the back, the other on the second floor in the front. The kitchen was recently renovated and the heating/air conditioning was replaced in 2024. The yard is spacious, with a fenced oyster shell yard featuring a firepit and off street parking for two cars. This home is turnkey - all furnishings and short term rental supplies included. Don't miss this rare opportunity!

Welcome to this luxurious, waterfront townhouse in the beautiful town of St. Michaels! This is the absolute total package, offering turn key comfort in a centralized location, allowing you to maximize everything the eastern shore has to offer. Enjoy the views of the majestic Miles River, boating from your personal, deeded boat slip, or walk across the street to the Eastern Shore's most premier golf course! This expansive unit offers premium upgraded finishes, a first floor ensuite bedroom, fireplace, and endless enhancements, including new windows and completely new HVAC system. Minutes to town for shopping or award winning dining experiences. This is truly the perfect waterfront, low maintenance getaway that is sure to check all of the boxes of a dream home!

Private waterfront retreat on Mill Creek offering beautiful views, spacious living, and all the peace and quiet you have been looking for. This custom-built Cape-style home is nestled on a serene, protected stretch of water and offers the ideal blend of comfort and tranquility. With 4 bedrooms and 3 full baths, the home features a flexible floor plan designed for both everyday living and entertaining. A cozy wood-burning fireplace anchors the open-concept great room, while large windows frame tranquil water views and flood the home with natural light. Beautiful hardwood floors flow throughout the main living areas, while two main-level bedrooms offer convenience and flexibility, including the Primary Suite with direct deck access. Step outside to a wraparound composite deck and enjoy your morning coffee overlooking the water—or take in the peaceful views from the bright breakfast area. Upstairs, you will find two additional bedrooms, and a spacious bonus room that could serve as a game room, media space, or guest bedroom. The full unfinished basement offers high ceilings and is ready for your vision—whether you're dreaming of a workshop, home gym, or additional living space. An oversized, climate-controlled two-car garage offers plenty of room for storage and projects. Outside, a private dock with 3 ft MLW includes an 8,000 lb boat lift, additional slip, a swim platform, and direct access to Mill Creek for boating, fishing, and crabbing. Spacious, private, and designed for comfort and connection—this is Eastern Shore waterfront living at its finest. Do not enter the property without an appointment.

**Seller to Provide $25,000 Credit for Desired Updates with a Full Price Offer.**The Sally Harris Mill House was once part of the Bloomingdale Estate is one of the remaining 18th Century masterpieces on the Eastern Shore. This peaceful farmette boasts over 31 acres with a blend of open pasture and wooded seclusion. The property sits on the Western banks of Madam Alices Branch, a tributary of the Wye River. Mature evergreens line the entrance creating a dramatic feel and historic charm is displayed throughout the home with 5 fireplaces, Flemish bond brickwork, and a gambrel roof. Modern amenities have been incorporated with the 2 story North wing which was completed around 2000 to include a first floor primary suite with en suite bathroom, makeup room, and 2 separate walk-in closets on the first floor and 2nd floor family room. The updated kitchen, partially finished basement with kitchenette, and heated pool are also highlighted upgrades. Outdoor living is celebrated here with a screened in rear porch for dinners in nature, a front porch to sit and watch the wildlife, and pool deck for making memories. Bring your machines and toys because there is plenty of storage in the outbuildings. The 2 story machine shop has been impeccably maintained and is perfect for any type of project. The open pasture would be perfect for horses and though they haven't been maintained in a few years, the forest contains nature trails for disconnecting from the hustle and bustle or hunting opportunities. This is your chance to make a piece of Eastern Shore's history your own peaceful retreat.

Experience breathtaking water views from every room in this 4-bedroom, 2.5-bath home, perfectly positioned between the Chesapeake Bay and Huntingfield Creek. With 1,845 sq. ft. of living space, this waterfront retreat boasts a gorgeous living room with soaring cathedral ceilings and a cozy propane fireplace. The kitchen features a propane cooking stove and lengthy counter tops for prepping .Step outside onto the expansive deck overlooking Huntingfield Creek, where 1.54 acres of serene natural beauty await. With 300 feet of waterfront, abundant wildlife, and a private duck blind, this property is a dream for nature lovers and outdoor enthusiasts.Boaters will appreciate the 40-foot pier equipped with water, electric, a 9,000 lb boat lift, and a 40-foot slip—all in great condition. While the home could use some updating, the unbeatable views and prime waterfront location make this a rare opportunity to create your perfect Eastern Shore getaway.

Serene Waterfront Retreat on Fairlee Creek is nestled in the tranquil woods of a private community just 10 minutes from the charming shops, museums, and dining of Chestertown, and the neighboring waterfront oriented town of Rock Hall. This stunning 4-bedroom, 2-bathroom waterfront home on Fairlee Creek offers the ultimate blend of seclusion, modern luxury, and effortless outdoor living. Imagine stepping out to launch your boat or kayak, or maybe just casting a line from your own private pier and floating dock—newly installed in 2025. Step inside this thoughtfully updated retreat, where every detail whispers move-in ready. The upper level welcomes you with an open-concept living area, dining area, and kitchen, all flowing outside onto a partial wraparound deck perfect for sunset cocktails or al fresco family meals. Cozy up by the wood-burning stove in the living room on crisp evenings, or entertain in the heart of the home with a gas range and new quartz countertops in the kitchen. The upper level bedroom invites you to start your day with private deck access and creek views. Venture downstairs to the versatile lower main level, featuring three generously sized bedrooms—one with direct waterfront vistas and french doors to the expansive lower deck and lush yard. The flexible family room adapts to your lifestyle, whether as a cozy office, kids' play haven, home gym, or media lounge, all with easy access to the outdoors. Recent enhancements shine throughout: fresh paint graces the entire house and decks (2025), while a brand-new roof installed on October 6 of this year ensures peace of mind for years to come. A new central HVAC system for the lower level, efficient mini-splits on the upper level, and bathroom remodels were all completed in September of this year. The septic system was replaced in 2021 with new BAT septic system, rated for 4 bedrooms. Outside, the magic truly unfolds. Extensive hardscaping creates an entertainer's paradise, anchored by an inviting fire pit for starry-night gatherings, barbecues, gardening, or simply soaking in the creek's serene rhythm. Your private pier and floating dock make water access effortless—launch kayaks, tie up your boat, or just watch wildlife drift by. Fairlee Creek provides a short trip direct to the Chesapeake Bay. Want a little less privacy? As a resident of this exclusive community, you unlock access to the Safe Harbor at Great Oak Landing Marina for a modest annual fee. Walk, ride a golf cart, bicycle, or drive to the marina and golf course and enjoy a resort-like lifestyle with a sparkling pool, seasonal waterfront restaurant, sandy beach, and golf course. Boat slip availability? Contact Safe Harbor directly to secure your spot at the marina. Enjoy priceless privacy in a wooded waterfront wonderland, with upgrades galore and the Chesapeake Bay lifestyle at your doorstep. Schedule your private tour today and claim your water-side paradise!

Elevated coastal elegance is displayed in this waterfront perched on the banks of Mill Creek. An open floor plan, radiant floor heating, high ceilings in the great room create an ambience conducive to a luxury weekend retreat or full time residence. Water views are celebrated from nearly every inch of the home and the large windows allow for a deep connection with nature. Outdoor living is a highlight with a covered waterfront screened in porch for crab feasts, fire pit with seating providing sweeping views of Mill Creek, and expensive rear decks on each floor. Two bedrooms on the main level make one floor living a breeze including the primary with ensuite bathroom and walk in closet. Stainless steel appliances adorn the kitchen. The great room is impressive, creating a magnet effect for family and friends. Upstairs has an bonus room perfect for your home office. This is a boater's paradise with direct access to the bay within minutes but protected waters at your shoreline. The private dock includes an additional floating pier suitable for kayak excursions. The front yard has thoughtful planting, pea gravel driveway, and potting shed. Across the lane is an additional lot that comes with the property and is currently used for storage. Feel a connection with the Eastern Shore and its waterways with this high end waterfront sanctuary just 15 minutes from the shops, galleries, and restaurants of historic Chestertown.

Welcome to 492 Pear Tree Point Road: an exceptional Chester River waterfront home with unique upriver views. Spacious rooms, gorgeous cherry hardwoods, a back deck to die for, private setting, and with space to add; this home has it all! Good water depth for a dock and center console. Nearly an acre of elevated land - out of the flood zone - that backs to picturesque horse pasture. The main floor features a huge open-concept kitchen and living/dining room space which naturally flows onto the unmatched second-story wrap-around deck; perfect for crab feasts, bbq, and watching summer sunsets. Perched on the second floor is the primary suite with private Romeo and Juliet style balcony high above. Ensuite bath is unfinished but is plumbed and ready for tile and final fixtures. Walk down the sunroom to the oversized two-car garage with workshop behind and the massive unfinished loft above. With electric and insulation already in place, this space is a blank canvas ready to be turned into a fantastic rec room or 4th bedroom. Finishing the loft and primary bath would make the home over 3,000 square feet of finished space and 3/4 bedrooms and 3 fun baths. Add the final touches to make this space your own. Walkout basement has tons of storage for outdoor equipment and has a bedroom and full bath. Open House Saturday October 18, 10:00 - 2:00. Come join us.

Welcome to this cozy ranch home located in the beautiful area near Chesapeake City, convenient to the Ben Cardin C&D Canal Trail, Schaefers Canal House, Chesapeake Inn and other fine dining restaurants. This spacious property boasts 3 bedrooms and 3 full bathrooms, kitchen with 42 cabinets, tile backsplash, pantry and Granite counters. As you enter the home, you are greeted with a wealth of interior features including wood floors, bar area with pellet stove, great room with Harmon pellet stove and a cozy woodburning fireplace in the dining room. The finished lower level offers extra living space with a large bedroom with woodburning fireplace and full bath, small music room, rec room and bilco door. Step outside to the expansive 9.5 acres of, mostly cleared land, complete with an above-ground pool, for those hot summer days, and 1000 sq ft paver patio with built-in fire pit and hot tub - ideal for outdoor gatherings and summer BBQs. For the car enthusiasts, the detached garage comes equipped with a car lift, making it easy to work on and store your vehicles. Additional features such as Hardy Plank siding, ceiling fans, and a hot tub add to the appeal of this amazing property. Don't miss your chance to own this exceptional home with a perfect blend of indoor and outdoor living spaces. Hunt or Skeet shoot in your own yard! Schedule your tour today before it's gone!

Welcome to Windwood: where meticulous pride of ownership truly shows on this classic Cape Cod on nearly 10 acres of serene, private land. With an expansive 4-bedroom main house and separate guest cottage; this home is perfect for a multi-generational family who are looking for separate spaces or for a family looking to generate more income by utilizing the guest house as a rental. This home really epitomizes quality 1960's construction and craftsmanship: solid brick and cedar siding, southern pine hardwood floors throughout, elegant keyhole crown moldings, a wonderful dining room fireplace, built-in shelving and cabinets, timeless dormers, and so much more. Coming up the circle drive you are received by a peaceful front porch; perfect for enjoying summer breezes and sunsets. Inside you are greeted to a welcoming foyer with a formal living room to your right and massive dining room to your left complemented by a wood-burning fireplace with intricate wood mantle. Moving back you will find the private main-floor primary suite with ensuite and large walk-in closet. The first floor further features a TV room and a recently renovated sun-room bump. out. Continuing on, the spacious kitchen with breakfast area was renovated in 2021 and now features honey-oak built-ins, custom cabinets, granite countertops, stainless steel appliances, propane or electric stove, a generously sized island with overhang seating, and LVP flooring. As you take the wide staircase upstairs you will find more gleaming hardwood floors that were just refinished. The second floor has three generously sized bedrooms; each with large closets and a smaller office space. Each end of the second floor features large attic storage areas. The full basement is partially finished with a spacious rec or workout room with a wood burning stove and new LVP floors. Across the brick breezeway, the guest house has also been recently renovated including all new kitchen appliances, walnut cabinets, washer/dryer, new floors, and upgraded bath. In front of the guest house is an attached two-car garage with additional areas for storage and tools. The backyard is a gardener’s dream and is fully fenced for the dogs and/or little kids. A small garden area, pergola and small fishpond complete the peaceful surroundings. Several walking trails have been cut out throughout the woods where you will find a large woodshed with plenty of storage. This wonderful property has so much to offer, you won’t want to miss it. Sellers have a $450,000 assumable VA Loan at a 2% interest rate. Recent updates include: roof tune up, exterior paint, interior hard floor refinish, interior paint, hvac service, and more.

Welcome to 101 Thicket Court in the sought-after Willow Branch East community, built with exceptional craftsmanship by Mike’s Custom Homes.This stunning 4-bedroom, 3.5-bathroom residence offers over 3,400 square feet of thoughtfully designed living space on a 1.25-acre lot. From the moment you arrive, the gorgeous custom front door makes a bold statement, setting the tone for the elegance within.The home’s exterior, finished in the serene Sea Grass siding, complements its timeless curb appeal. Step inside to discover a bright and open floor plan with high-end finishes throughout. The heart of the home features a kitchen with quartz countertops, custom cabinetry, and premium fixtures, seamlessly flowing into spacious living and dining areas—perfect for both everyday living and entertaining.Retreat to the private owner’s suite with a bath, while three additional bedrooms provide comfort and flexibility for family or guests. The walkout basement offers endless possibilities for recreation, storage, or a future home gym or theater. Rear 35x20 DeckSituated on a generous lot, this property offers both privacy and space to enjoy outdoor living. Every detail has been considered to bring together comfort, style, and functionality in a home you’ll be proud to own.

Discover the charm of this exquisite transitional Victorian home nestled just off the beaten path in downtown Chestertown. Built in 2011, this stunning residence boasts meticulously maintained living space, featuring an open floor plan that seamlessly blends comfort and style. The interior showcases beautiful wood floors, exposed beams, and an abundance of natural light from skylights and double-pane windows, creating an inviting atmosphere throughout. The owner's suite is located on the main floor with a beautiful new ensuite bathroom. On the second floor, you will find another living area with an additional 3 bedrooms and bathroom. Cozy up in the living area by the Vermont Castings pellet stove, perfect for creating lasting memories. The main floor laundry adds convenience to your daily routine. Step outside to enjoy the wrap-around porch, screened porch, and balcony, all overlooking the beautifully landscaped yard, ideal for entertaining or simply unwinding in your private oasis. The attached garage and paved driveway provide ample parking for you and your guests. Encapsulated crawlspace with room for storage. This home is just a short walk from historic downtown with all of the amenities like shopping, dining, farmers market and theater.

Big, bold, and beautiful! This wonderfully updated 2 story brick colonial in Chestertown is just minutes walking to the shops, restaurants, college, and waterfront. The first floor is enhanced with a finished sunroom with mini split, well appointed full bathroom adjacent to the office, and the kitchen of your dreams. Traditional aspects remain with a spacious dining room with built ins and living room with fireplace. The upstairs has 4 bedrooms including the primary suite with dressing room, private balcony and en suite bathroom equipped with radiant floor heat. Half of the third floor is finished as well with a mini split and skylights for hobbies while the other half is perfect for storage. Not that storage is a issue with this full basement including a workout room and dance studio as well. The lush grass yard is tastefully landscaped and easily enjoyed with privacy on your rear deck. Keep your cars and favorite toys clean with the 3 car garage. Spare no detail and live luxuriously in this Eastern Shore gem.

THE BEST OF WATERFRONT LIVING AND THE BEST VIEWS IN THE DEVELOPMENT with year-round views of Spa Creek in the Sought After, Gated Community, THE YACHT CLUB CONDOMINIUMS! Enjoy the ultimate Annapolis Lifestyle where you can dine dockside, paddleboard at sunrise, take a dip in the waterside pool or catch the water taxi to downtown Annapolis. Step inside to this immaculate unit and call it home. The Community Amenities elevate the experience with a clubroom, fitness area with shower facilities, waterside pool, grilling area, deep water marina access, assigned parking, secure storage area and pet-friendly!This spectacular 2 Bedroom, 1 Bath unit was converted to a 1 Bedroom to add a Dining Room to boast the spectacular views and could be easily converted back to 2 Bedrooms. You will LOVE the open floorplan, the Bright Kitchen and water views from every angle! This unit is being sold furnished, don't wait, schedule your tour today! Condo bylaws require a 15 day right of refusal before settlement.

A BOATER'S DELIGHT, this waterfront rancher in Chester River Beach is a small slice of paradise! Enjoy deep, protected water (5ft mlw) and tranquil views of Winchester Creek. As you enter the home, you'll be captivated by the open concept kitchen and living room with expansive water views. The updated kitchen showcases white cabinets and granite countertops. The fully conditioned four season room is perfect for enjoying the views all year long and has brand new high quality windows and slider door! Features 3 bedrooms, 2 full bathrooms and an expansive 2 car garage that's large enough to fit a 25 foot boat w/ trailer inside. The primary ensuite bathroom has been gorgeously updated with floor to ceiling Italian tile. Brand new wood grain tile is featured throughout the main living areas. New roof, new HVAC, and new appliances! The pier features a 15,000 lb boat lift and deep water! Chester River Beach features a community waterfront park, picnic area and pavilion as well as a boat launch and community pier with boat slips. Enjoy the convenience of being minutes from the Kent Narrows dining and entertaining experiences by car or boat! 10 minutes to the Bay Bridge! Schedule your showing today!

Handsome farmhouse on 36 acres. House maintains much of its original character. Spacious rooms and beautiful views.

This is a stunning property! It combines elegance and functionality with its spacious layout, beautiful finishes, and thoughtful details. The open floor plan, combined with the cozy living room, pocket doors, and built-ins, creates a welcoming atmosphere. The kitchen, with its quartz countertops and wood floors, is a great space for cooking and entertaining. The main-level split bedroom floor plan offers great privacy, especially with the large owner’s suite and the nearby laundry room. The screened porch with its cathedral wood ceiling and skylights is a fantastic spot to relax and enjoy the private backyard.The upstairs family area is a perfect place to unwind, with the wood flooring and built-ins adding warmth and character. The two additional bedrooms are also generously sized, and the shared bathroom with double sinks and a walk-in shower is a great touch. Plenty of storage with the walk-in attic.Plus, the oversized two-car garage with room for a small workshop is a bonus for hobbyists or those needing extra storage space.Being just a mile from Historic Downtown Chestertown and close to the Chester River Yacht and Country Club adds so much appeal to this home. It really is a one-of-a-kind find.

Enjoy waterfront living in this charming 3-bedroom, 2.5-bath rancher perfectly sited on 1.37 acres overlooking the tranquil waters of the Tuckahoe River. This spacious, single-level home is filled with natural light, boasting an open floor plan and featuring waterviews from nearly every room. The spacious kitchen features stainless steel appliances, a gas stove, bar seating, and overlooks both the dining and living areas. A large living room is anchored by a cozy wood stove with stone hearth. The dining room’s expansive bay window captures stunning river views and opens to the generous screened porch. The primary suite boasts vaulted ceilings, dual closets and another beautiful bay window framing the water. Two guest bedrooms feature hardwood floors and the guest bath includes a shower/tub combo and linen closet. A separate laundry room includes a convenient half bath with exterior access—perfect for pool days. Enjoy the bright and inviting sunroom, which overlooks neighboring farmland or retreat to the private backyard oasis. A new in-ground pool with retractable cover and concrete patio sits just beyond the screen porch overlooking the park-like grounds. Boaters and water lovers will appreciate the private dock, complete with two 10,000-lb boat lifts, two personal watercraft lifts, a swim ladder and deep water (approx. 8’+), ideal for fishing, crabbing, or cruising the waterways of the Eastern Shore. Additional features of the home and property include a detached two-car garage, a storage shed with an electric garage door, great for lawn/boat equipment, and peace of mind knowing the property is outside the flood zone. Recent upgrades include a new roof and siding (2025). This exceptional property is a true Eastern Shore gem.

Welcome to this beautifully maintained 4-bedroom, 3-bath home offering serene views of the Chesapeake Bay in the quiet and friendly community of Tolchester Estates.This wonderful home is nestled just 10–15 minutes from the cities of Chestertown and Rock Hall. This close proximity provides access to shopping, restaurants, a farmers market, theater and local arts. The area abounds with hunting, fishing, crabbing, boating, and much more. A local full-service marina with a restaurant, summer concerts, and a beach is only 5 minutes away.The main level of the home provides a light-filled open layout featuring gleaming hardwood floors on the main level and expansive windows offering lovely views to the Chesapeake Bay. The beautiful living room features new built-in custom cabinetry flanking a cozy gas fireplace, with seamless flow into an all-season sunroom and multiple decks—perfect for entertaining or unwinding after a hectic day.The living room adjoins a fully appointed chef’s kitchen with a gas cooktop, wall ovens, refrigerator, and dishwasher. There is plenty of cabinetry, along with an inviting eat-in area and high-top breakfast bar with seating, and access to the decks for grilling. A formal dining room just around the corner offers additional space for hosting.The first-floor primary suite is a private retreat with direct deck access and water views. The ensuite bath features a double vanity, jet tub, and separate shower, complemented by a walk-in closet and laundry area for ultimate convenience. A second bedroom with an attached full bath completes the main level, with both bedrooms updated with new carpet in 2023.Upstairs, you'll find newer luxury vinyl plank flooring, 2 additional bedrooms, and a full bath. The generously sized water facing bedroom provides a great view and is sized for a suite full of furnishings or is ideal for a “bunkhouse” type setup, ideal for guests or family. The rear 4th bedroom completes the upper level and features an entry into the walk-in attic storage.The oversized, rear-entry 2-car garage includes built-in cabinetry and provides 1 of 2 inside entries to a full unfinished basement—ready for your vision. Recent updates include a brand-new roof the week of May 5, 2025), a propane-fired whole-house generator, custom living room cabinetry, upgraded insulation, all new multi-faceted water treatment systems, and custom structural enhancements.Don’t miss this rare opportunity to own a peaceful bay-view sanctuary with modern upgrades and timeless charm. Your Chesapeake escape awaits!

Welcome to 1600 Liberty Road: the perfect home for a growing family in a great location. Quality craftsmanship in this new construction truly shows while the list of features goes on and on: Brazilian Cherry hardwood floors, 9 foot tray ceilings, bay windows, ceramic tile kitchen and baths, brushed nickel fixtures, a electric fireplace, oversized back deck and so much more. This home has so much natural light and really celebrates the views of the surrounding farmland. The gourmet kitchen features quartz countertops with overhanging bar, stainless steel appliances, double sink, quiet-close drawers and more. The kitchen / breakfast area flow seamlessly into the expansive open concept living and formal dining rooms. Easily step out of the living room and onto the oversized back deck. The main floor also features a second living room / family room or an office space. Continuing upstairs, the luxurious owner's suite has great views of the surrounding farmland. The 3 additional comfortably sized bedrooms with large closets and another full bath complete the second floor. The fully finished basement has another bedroom with full bath and laundry room with separate exterior entrance. This completely separate space could easily be turned into a rental for extra income. Private backyard features a tall privacy fence: perfect for entertaining and plenty of space for the kids and pets. Plenty of parking with an oversized 2-car garage and concrete paved driveway. All systems and appliances come with a one-year manufacturer's warranty. Minutes away from shopping, dining, and entertainment: this property is ideally situated for an easy commuting lifestyle. Schedule an appointment today!

This immaculate, 5-bedroom, 3-bath Colonial is ideally positioned on the coveted Bennett Point peninsula, set on a private 2+ acre partially wooded homesite. Thoughtfully upgraded inside and out, the home now offers smart home functionality, fresh interior paint, and a truly move-in ready experience. Outdoor living shines with a heated saltwater pool, elegant paver patio, and built-in gas fire pit—enhanced by privacy fencing, professional landscaping, and curated lighting. A shed provides stylish storage for pool and lawn essentials. Inside, the chef’s kitchen flows seamlessly into the dining area with slider access to the screened porch—ideal for elevated entertaining. Wood-look tile floors anchor the main level, which also includes a first-floor bedroom with full bath, a sun-filled family room, and updated lighting throughout. Upstairs, the spacious primary suite offers a walk-in closet and en-suite bathroom, complemented by three additional generously sized bedrooms and a full hall bathroom. An oversized driveway provides ample parking. Enjoy nearby water access at Bryantown Landing on the Wye River. Only minutes to Prospect Bay Country Club and Queenstown Harbor Golf Club. Easy commuting access to Easton, Kent Island, and Annapolis. A refined blend of privacy, modern comfort, and Eastern Shore lifestyle—this exceptional home is ready for its next chapter.

Spacious 4-Bedroom Home with Pool on Nearly an AcreWelcome to your dream home! This stunning 4-bedroom, 2.5-bath residence offers over 3,200 square feet of thoughtfully designed living space, perfectly situated on nearly an acre of beautifully landscaped land. With a seamless blend of comfort, elegance, and outdoor luxury, this property is ideal for both everyday living and entertaining.Step inside to find a bright and open floor plan featuring spacious living and dining areas, a modern kitchen with ample cabinetry and counter space, and a cozy family room with a fireplace. The generously sized bedrooms include a serene primary suite with a private ensuite bath and custom large walk-in closet.Enjoy the best of outdoor living in your private backyard oasis, complete with a sparkling inground saltwater pool, expansive patio, and plenty of green space for play or gardening. Whether you're hosting a summer barbecue or relaxing with family, this home has it all.Additional highlights include a two-car garage, dedicated laundry room, and a convenient location close to schools, parks, and shopping. Don't miss this rare opportunity to own a slice of paradise with room to grow!

This waterfront farmette is a rare find just a few minutes from downtown Chestertown and features extensive updating. The new kitchen, 2 new full bathrooms, and new roof all from 2024 just to name a few have you set up for many years to come. Most of the property is cleared and grassy making it perfect for your equestrian retreat on the water. A detached 2 car garage is perfect for vehicles or water toys. The river room is flooded with natural night and offers prime views of the surrounding wildlife. Stay cozy with the wood burning fireplace. Fishing and hunting are prime in this location. Feel a sense of peace and tranquility on this very private 9 acres while being able to drive to the historic district for the shops, art galleries, theatre, and restaurants in less than 10 minutes. Chestertown is located just 1.5 hours from Washington DC, Philadelphia, and Baltimore.

Nestled in the serene Orchard Hill community, this stunning Craftsman-Colonial offers 3,735 sq. ft. of luxury and comfort. The open, light-filled floor plan showcases rich hardwood floors and elegant finishes throughout.The gourmet kitchen features upgraded countertops, pecan wood-stained cherry cabinetry, stainless steel appliances, including double ovens, a gas cooktop, and a tankless water heater. It opens to the family room with a cozy corner gas fireplace—perfect for entertaining or relaxing.The main level includes an office, primary suite with a large bath and walk-in closet, an additional bedroom and full bath, and a dedicated laundry area. A screened-in porch off the main floor provides a peaceful space to enjoy morning coffee or evening gatherings surrounded by nature. Upstairs offers an open sitting area with window seat, two additional bedrooms, and a full bath.Set on a beautifully landscaped 2.81-acre lot backing to trees, this property provides a private outdoor retreat. Additional highlights include a side-entry garage, paved driveway, and outbuilding for extra storage.Experience the best of Orchard Hill living—where quality, comfort, and natural beauty come together.

Just steps from the Chesapeake Bay this charming rancher offers 3 bedrooms, 1.5 baths all on convenient, one level living. The kitchen is the central gathering space in the house with gleaming quartz countertops and beautifully refinished wood floors. The floorplan is open, yet provides cozy places for reading and relaxing. Owner upgrades include new white 5-panel doors and moldings to accentuate the classic architecture. Upgraded electrical outlets feature USB/C charging ports. Comfy hot water baseboard heat keeps you toasty in winter and a newer central AC system cools you in summer. The large front porch has pet-proof screens and lots of room to relax with friends. Solar panels keep electric bills low.A new (2025) 24 ft x 24 ft outbuilding features garage/workshop space on the first floor and an accessory dwelling unit (ADU) on the second level. This building incorporates energy efficient features like closed-cell foam insulation and R-60 roof insulation. There are 9 ft ceilings in the garage and cathedral ceilings in the living space above. An additional shed provides more storage space.This Beach Road location offers in-town convenience and is within walking or biking distance to restaurants, the beach and marinas. Call for your private tour today.

An impeccably maintained, perfectly positioned two bedroom, two and one-half bath condo featuring one of the best vistas of Chestertown and the Chester River. Here, body, mind, and spirit naturally align - it's simply impossible not to feel balance. River House, with only five private residences, occupies the best real estate within this prized, friendly and well managed neighborhood called Chester River Landing. Historic downtown Chestertown and the Chester River Yacht & Country club are less than 2 minutes away, when you need a break from your enclave that includes marina, grill patio, crabbing/fishing pier, beach area for kayak launch, waterfront green space with fire pit, community garden, and pool with pool house. Unit 201 includes a nearby 1 car garage with overhead storage racks and a deeded premium boat slip (A7) A unique feature of this home is a custom HVAC and air quality system, ideal for anyone with seasonal allergies, chemical sensitivities, or just appreciative of quality air and healthy living. New GE range, LG and 03 Pure Eco Laundry System installed 2025. (Warranties convey). The lobby and all common areas have recently been beautifully redecorated and furnished. As part of CRL commitment to maintaining property excellence, the entire exterior of River House is currently receiving new siding, flashing and other pro-active improvements at no cost to the new owners.

Countryside elegance at its finest in this sprawling and updated Dutch Colonial in the rolling farmlands of Worton. A tasteful blend of traditional colonial character along with modern amenities creates your perfect setting for a peaceful retreat. The primary suite includes cathedral ceilings, private balcony, and a beautifully remodeled en suite bathroom. The spacious living room gracefully flows out to a private screened rear porch. The den or office has wonderful built-ins and feels cozy with one of the 2 fireplaces in the residence. Stainless steel appliances and natural light make this spacious kitchen a hit for entertaining large groups. A half bathroom on the first floor also is perfect for receiving guests. Upstairs are two large bedrooms and another full bathroom. The basement is perfect for storage or your next project and one side even has a garage! Outdoor living space is the true hit with this property. Life can be enjoyed on the full length covered front porch with Ipe flooring or on the large back deck. Thoughtfully curated landscaping has created a tranquil oasis including a fenced in rear yard perfect for pets. The property is located just a short drive from Historic Chestertown and less than 2 hours from Philadelphia, Washington DC, and Baltimore.

Showings and Back Up Offers Encouraged. Sitting on 11+ acres, this 5 bedroom 3 1/2 bath Colonial with 2 car garage home is ready for new owners. New Carpet and Flooring throughout the home. Newly painted interior with black trimmed detail on interior doors. Updated light fixtures, bathroom fixtures and faucets! Main level features formal living room, dining room. and open family room complete with gas fireplace. Full kitchen has plenty of cabinet space and bar area, adjoining the Sunroom adorned with windows and a sliding glass door for plenty of sunlight that opens to your wooded paradise behind the home. Main level also has a half bath in the hall, as well as main level laundry- washer and dryer included. A bonus feature is a large room with full bath that can be your Main Level Master, or in law suite/guest suite. Upstairs are 4 nice sized bedrooms with ample closet space, full bath in hall way and Master bedroom with full bath to include soaking tub and double vanity sink. Home comes complete with a Masters Water Softener system and 2 new HVAC units (2.5 & 3.5 ton) installed in July 2022. Septic system was fully repaired and upgraded and is functional (see Disclosures). Home features a shed to store your riding mower and gardening gear. Home has its own shooting range and is surrounded by tall trees and Nature abound! Enjoy your wrap around front porch on cool Fall nights listening to the birds in the trees! This is your country living paradise less than a mile off of Rt 12. Home is owner occupied. Schedule your showing today!

Welcome to this private cold-de-sac in Colesville, Maryland. This home offers a half-acre lot that is fitting for outdoor activities, social gatherings, and business ventures. Large basement space that extends underneath the garage. Close proximity to I-495 and Maryland Route 200. Recreational buildings and parks are less than miles away. This is suburban living at its best.

Lovely colonial in Country Club Estates. The property goes back to Country Club Lane. 3 bedrooms and 3 full baths. One of the full baths is on the first floor so there is potential for a main floor bedroom. Screened-in porch overlooking the landscaped yard. 2 gas fireplaces. Open kitchen to family room. Mature landscaping. Nicely set back from the road. Well water, public sewer. Side entry garage charming shed. Beautiful wood floors. Close to town and Chester River Yacht and Country Club. Well-kept home ready for its new owners.

The luxury waterfront lifestyle is awaiting you on Spa Creek in Eastport. This updated unit has the exterior wall opened up for a picture window to let in natural light, a modern kitchen with stainless steel appliances, and a high end mini split system for silent and efficient heating and cool. The flow of the unit is one of the highlights with the kitchen and living room opening out to the covered and private outdoor deck. Moments are to be enjoyed here with views of the yachts meandering along Spa Creek with historic Annapolis in the backdrop. The community amenities include a waterfront pool to relax and enjoy the best views in town, outdoor grilling and dining area, exercise room, and sauna. Storage space is made easy with an assigned storage unit and also a bicycle room for additional space. This maintenance free condo is walking distance from the greatest marinas and dining options in Eastport and just a short water taxi ride from City Dock.

Rare lakefront opportunity in Kent County offering exceptional privacy and a peaceful natural setting. Tucked away on 2.62 partially wooded acres along Urieville Lake, this beautifully situated property provides a secluded retreat where you can truly unwind and enjoy the outdoors.This spacious 4-bedroom, 3.5-bath home offers flexible living for families and guests alike. The layout includes the option for a first-floor bedroom, three bedrooms on the second level, and an additional bedroom in the finished walk-out basement, providing plenty of room for everyone while maintaining privacy throughout the home.The open-concept main living area is filled with natural light and showcases beautiful views of the surrounding woods and the lake beyond, creating a warm and inviting space for everyday living or entertaining. The home features two full bathrooms on the second floor, a full bath on the lower level, and a convenient half bath on the main floor, all designed with comfort and functionality in mind.The finished walk-out basement adds valuable living space with a bedroom and full bath—ideal for a guest suite, recreation room, home office, or entertainment area—with direct access to the peaceful backyard and lakefront setting.Outside, the property truly shines. The 2.62 acres offer a rare level of privacy, with mature trees and natural surroundings that create a quiet, secluded atmosphere. Whether you're relaxing by the water listening to the geese, gardening, exploring wooded paths, or enjoying lakeside sunsets, this property offers endless opportunities to connect with nature.Situated on Urieville Lake, residents can enjoy fishing, kayaking, and small boating right from their own backyard. The lake spans approximately 35 acres, shaped like the letter “Y,” and supports a healthy fishery including largemouth bass and bluegill, along with occasional catches of pumpkinseed sunfish, brown bullhead catfish, golden shiners, and common carp.If you're searching for a private waterfront escape in Kent County, where nature, space, and tranquility come together, this special property is ready to welcome you home.

Immaculately maintained oasis! Rurally located, 3-4 bedroom, 2 1/2 bath Cape Cod offering 2,656 sq. ft. of living space and situated on 2.3 beautifully landscaped acres in the sought-after community of Strawberry Hill in Warwick, Maryland, with close proximity to Chesapeake City, Kent County, MD and Middletown, DE. Main level highlights include hardwood flooring in the living room, formal dining room and family room which flows into a roomy eat-in kitchen. Kitchen details include sleek granite countertops, stainless-steel appliances, attractive white cabinetry, propane cooking and sliders leading to the deck and backyard. Located adjacent to the family room is a spacious screened-in porch, accessed by French doors, featuring a lofty vaulted wood ceiling with skylights. Perfect for large family gatherings and entertaining! Additional main level details include a spacious primary bedroom with hardwood flooring, walk-in closet and attached bath, as well as a convenient half bath and laundry room with garage access. Upper-level features include bedroom two offering a walk-in closet and access to a sprawling Jack and Jill bathroom, a third bedroom with 2 double closets and an attached 12' X 11' bonus area, which could be utilized as a nursery or sitting room. Additional upper-level details include a walk-in floored attic area with plenty of storage space, as well as a recently updated 33' X 12' bonus room/home office/4th bedroom offering striking hardwood flooring, closet, a vaulted ceiling and stairs leading to separate garage access. Additional property details include an immaculate basement, side entry 2-car garage, circular driveway, large playset, patio, an expansive well-manicured lawn and a 36' X 28' workshop. Workshop details include a garage door and lean-to featuring electric, heating, work bench, shelving and durable epoxy flooring. Ideal for the hobbyist or mechanic! Recent upgrades include a new pressure tank and water softener added in 2024. Shows pride of ownership. If you are searching for an off the beaten path, well maintained and spacious place to call home, your search is over...98 Blakiston Lane...Welcome Home!!!

Welcome to 23290 Ninetown Rd! A BRAND NEW 4 bedroom, 2 bath home crafted by Lomaxx Custom Homes on a beautiful 4.32 +/- acre lot with a peaceful stream on the property!An open concept, gleaming quartz countertops, and thoughtful design invite you to live, gather, and grow. This isn't just a house-it's the beginning of something beautiful. Come on in and make yourself at home

Waterfront living in Eastport—renovated, reimagined, and ready to enjoy. This light-filled condo has been smartly reconfigured to maximize both space and views, with a custom-installed picture window that pulls in natural light and frames Spa Creek beautifully. The open-concept layout flows easily from kitchen to living area to the oversized private deck—where waterfront living truly shines.The deck offers front-row views of Spa Creek and the marina, with plenty of room for both dining and lounging. It’s been upgraded with a custom awning system that encloses all sides for shade and shelter, plus water-resistant polypropylene flooring for year-round function and durability. Inside, the updated kitchen features custom cabinetry, Corian countertops, and stainless steel appliances. Solid hardwood bamboo flooring runs throughout, laid over Bella Premium underlayment for extra comfort and sound absorption.Two newer Mitsubishi mini-split HVAC units handle heating and cooling efficiently. Additional updates include in-unit washer/dryer, smart built-in cabinetry, induction stovetop, and thoughtfully updated fixtures and finishes throughout. The unit includes secure building storage, plus general and assigned parking—conveniently located close to the entry for easy unloading.This secure condo community offers some of the lowest monthly fees in Eastport and a truly prime location—right on the edge of Spa Creek, at the end of a dead end street, so it is nice and quite, right next to Burnside Park. The list of amenities includes a waterfront pool, clubroom, fitness studio with showers, an outdoor grilling/dining area overlooking the water and kayak storage as well as a launch point. A deep-water marina is just steps away, and you’re minutes from downtown via water taxi. Pet-friendly and short-term rental–friendly—ask for details.

Queen Street Gem! Located in the historic section of Chestertown, walk to the restaurants, shops, theater, farmer's market, and waterfront. Beautiful woodwork and pocket doors. Spacious rooms, hardwood flooring, solid wood doors, thick moldings, and ample closet space. Featuring 5 bedrooms and 2.5 baths, with 3 bedrooms on the second floor and 2 additional bedrooms on the 3rd floor. Bathrooms have been updated. Wide front porch. Adorable fenced-in rear courtyard. This property has a ton of character and charm. Just waiting for its new owners!

This meticulously maintained home, nestled on a nearly half acre lot on a cul-de-sac offers 3,780 square feet of luxurious living space, complete with an oversized attached garage. Upon entering through the front door, you are immediately greeted with a bright open foyer. Gorgeous hardwood floors have been sanded and re-stained, adding to the homes warm and inviting atmosphere. The Main floor has 9 foot ceilings and the spacious gourmet kitchen is a dream, offering a gas stove, oven, microwave, refrigerator, dishwasher, and a convenient garbage disposal—newly replaced in 2025. Thoughtfully designed, it also features slide-out drawers for easy access to cookware and essentials. There is also extra storage below your oversized island which accommodates stools. Enjoy casual meals in the breakfast room surrounded by windows and complete with a ceiling fan. The breakfast room opens onto composite steps (added in 2023) leading to a cement patio ideal for outdoor dining or relaxation. The patio overlooks a sparkling inground pool with new pool motors installed in 2024. The fully fenced backyard is surrounded by elegant white vinyl fencing and also includes a charming gazebo creating a serene retreat. Looking in from the kitchen is a spacious carpeted family room with a gas fireplace and a ceiling fan perfect for relaxing or entertaining.  Also on the main floor is a dining room, office/living room, a half bath, and a mudroom with laundry that leads to the garage. Upstairs you'll find four generously sized bedrooms and two beautifully tiled bathrooms. The massive primary suite offers a peaceful sitting area, a lighted tray ceiling, and a ceiling fan for added comfort. Two walk-in closets provide ample storage while the ensuite bathroom boasts a stand-alone shower, a luxurious slipper soaking tub, and brand-new floor tile (all installed in 2021) for a spa-like experience. The finished basement is an additional highlight and ideal to host movie nights. It has another tiled half bath with a large closet. There are also two large storage rooms off the finished basement. There is a new whole house water treatment system installed in 2021  ensuring top-quality water throughout the home.  Ideally located just minutes from I-95, Route 40, and Delaware, this home is centrally situated between Philadelphia and Baltimore providing easy access to major cities while offering a peaceful, suburban oasis. With every detail thoughtfully updated and maintained, this home is truly move-in ready and ready to welcome you! Come tour your new home!

Price improvement! Prepare to be wowed when you walk through the front door. Gleaming hardwood floors, huge floor-to-ceiling windows, high-end kitchen and primary bath. Floor plan that flows beautifully. 4 bedrooms and 2 baths. Wood burning fire place in the living room. House is filled with natural light. Two car garage under the house with unfinished basement. Windows, roof, appliances, and HVAC have all been replaced. Electric has been updated. The list of improvements goes on. Come see this for yourself. It's gorgeous!

Welcome Home to Your Move-In Ready Dream Retreat! Nestled on nearly an acre of land and privately set back from the main road, this beautifully designed home offers the perfect blend of privacy, functionality, and modern luxury—no need to wait for new construction when this gem is ready for you now! As you step inside, you're greeted by a spacious foyer that leads into a dedicated home office and a convenient half bath. Just around the corner, a thoughtfully designed mudroom connects to the attached garage, providing an ideal drop zone for daily living. The heart of the home is the stunning kitchen, featuring granite countertops, a stylish apron-front sink, brand-new appliances, and island seating perfect for casual dining and entertaining. The open floor plan flows seamlessly into a generously sized living room and formal dining area—an ideal space for gatherings. Upstairs, you'll find four spacious bedrooms, including a centrally located laundry room for added convenience. The luxurious primary suite is a true retreat, boasting two oversized walk-in closets, a cozy sitting area, and a spa-like en-suite bathroom complete with a freestanding soaking tub and a large walk-in shower. Step outside to enjoy your newly constructed Trex deck, perfect for relaxing or hosting guests, all overlooking your freshly fenced-in backyard with ample space to add a pool and create your own outdoor oasis.Don’t miss the opportunity to call this property your forever home—schedule your private showing today!

Motivated Sellers, bring all reasonable offers! Beautifully Restored 1890s Victorian in Trappe, MD - 6BR, 3.5BAStunning fully restored 1890s Victorian in the heart of Trappe. This spacious 6-bedroom, 3.5-bath home features a wraparound porch, formal living and dining rooms, a family room, and a marble primary bath. The home offers one gas fireplace for warmth and ambiance, plus four original decorative fireplaces that add timeless character throughout.The modern kitchen includes stainless steel appliances and a 36 gas range.Updated throughout with all-new plumbing and electrical, spray foam insulation, new windows, and a 4-zone heating system. Outdoors, enjoy a large slate patio and generous off-street parking. A rare blend of historic charm and modern efficiency -move-in-ready.Call Today for a Tour!

Experience refined living at 156 Sunnybrook Drive in Elkton, Maryland. This beautifully appointed Colonial offers 2800+- sq. ft. of exceptional living space on a private 1.13-acre corner lot in the desirable Bohemia Manor School District. Step inside to an inviting open layout where the kitchen features granite counters, stainless steel appliances, and a charming breakfast nook that flows effortlessly into the warm and welcoming family room. With 3 spacious bedrooms, 2.5 baths, and main-level laundry, this home is designed for both comfort and convenience. The primary suite offers a serene retreat with a bathroom featuring a soaking tub and separate shower. The finished lower level provides an extended living area complete with a woodstove, new carpet and paint, bilco outdoor access, and ample storage. Thoughtful upgrades such as a Rinnai on-demand water heater, Rain Soft water system, 2-car garage, owned solar panels, and a 50-year architectural roof elevate the home’s quality and efficiency. Outdoors, the property truly shines. Enjoy a resort-style setting featuring a fenced rear yard, low-maintenance deck with PVC railings, and a sparkling inground pool with a 2022 liner—perfect for elegant summer entertaining. The impressive 32x24 pole barn with electric offers endless possibilities for hobbies, storage, or workspace. All of this is complemented by an ideal location just minutes from waterfront dining, boutique shops, and the charm of Historic Chesapeake City. With no HOA, this property combines luxury, privacy, and convenience in one exceptional offering.

Spacious Townhome with Golf Course Views and just 1,000 feet walk to Bay Hills golf clubhouse.Property OverviewThis large townhome overlooks the 17th golf hole at Bay Hills Golf Club, offering impressive views of the course. The home features four spacious bedrooms and three and a half bathrooms, providing ample space for family and guests.Outdoor and Entertaining SpacesEnjoy entertaining or simply relaxing on the oversized deck, which offers beautiful views of the 17th fairway. The deck is ideal for gatherings, outdoor dining, or enjoying peaceful evenings surrounded by the natural beauty of the golf course.Interior FeaturesThe main level boasts bright and open living spaces, creating a welcoming atmosphere. The finished lower level includes a fourth bedroom that may also serve as a family room. This space features a full bath and provides convenient walkout access to the outdoors.Recent UpdatesRecent improvements make this home move-in ready, including brand new flooring, new carpet, and fresh paint throughout. Additionally, a new roof was installed just six months ago, ensuring durability and peace of mind.Community Amenities and LocationLocated in the desirable Bay Hills community, residents enjoy access to amenities such as golf, a pool, tennis courts, and a clubhouse. The property is conveniently close to Annapolis, Severna Park, shopping, dining, and major commuter routes.

Spacious Waterford Model with Over 4,800± Sq. Ft. on .32 Acre LotThis Waterford model offers exceptional living space and thoughtful design, situated on a .32-acre lot in a quiet, established community.Boasting approximately 4,800± square feet of total living area, this home features a brick front and a 2-car garage.The main level welcomes you with gorgeous hardwood floors and a gourmet kitchen equipped for culinary enthusiasts. The kitchen opens to a bright breakfast room with access to a deck overlooking a large, level yard that backs to protected woods, providing privacy and a natural setting.The cozy recreation room includes a gas fireplace, architectural columns, and a bump-out that adds extra space for relaxing or entertaining.The expansive main bedroom suite is a private retreat, featuring a sitting room, tray ceiling, and a spa-like garden bath. Additional convenience is offered with a second-floor laundry room.The home currently includes four spacious bedrooms, with potential for six total. The walk-out basement has framed rooms with windows ready for finishing to create additional bedrooms, a media room, or flexible living space. The basement also includes a finished recreation room with a full bath and loads of storage space.Additional highlights include an owned propane tank, eliminating lease concerns, and a $480 yearly HOA fee.Property details include four bedrooms with potential for six, 3.5 bathrooms, a 2-car attached garage, a .32-acre lot, approximately 4,800± square feet of living area, and a $480 yearly HOA fee.This home combines space, style, and privacy in a desirable location, offering tremendous flexibility for your lifestyle and future growth.

Don't miss this rare opportunity to own one of the only waterfront lots still available on the Chester River! Perfectly positioned just across the river from the historic charm of Chestertown, this premier property offers front-row access to the area's beloved events, including the Tea Party Festival, Fourth of July celebrations, and the Dickens Festival.Situated in a highly desirable and tranquil location, this lot has been lined with California privet bush and mostly cleared to reveal unobstructed views of the Chester River. The invasive phragmites is scheduled to be sprayed soon! Enjoy direct water access with the potential to add a dock and access deep water off the shore. Imagine your custom-built dream home or weekend escape!This is a once-in-a-lifetime chance to build your ideal waterfront retreat in one of Maryland’s most scenic and culturally rich areas. Call to schedule your private showing today!

Stunning waterfront property with private dock site on the Chester River. The house has been gutted and needs a complete rehab, or it can be removed and rebuilt to suit your dreams. Building plans are available. The property features a brand-new BAT septic system that has yet to be connected. Beautiful location and views! Just a short drive to Chestertown. 3 ft mean low water, buyer to verify.

Welcome to 408 Laurens Way, located at the end of a quiet cul-de-sac in the heart of Queen Anne’s County. This beautifully maintained home offers nearly an acre of privacy, backing to open agricultural land. With approximately 2,400 square feet of living space, the property includes 3 bedrooms, 2.5 bathrooms, a spacious family room with a fireplace, a formal dining room, and an additional flex room that can serve as an office or den.Since purchasing, the sellers have made extensive updates, including a new roof, new HVAC system, fresh insulation and vapor barrier, new carpeting in all bedrooms, updated appliances, fresh interior paint, and more.The exterior features a thoughtfully designed hardscape, outbuildings, chicken coops, and plenty of outdoor space for recreation or gardening. The attached garage provides overhead attic storage with easy access.Experience the tranquility of Maryland’s Eastern Shore in this meticulously cared-for property, ready to welcome its next owner.

Stunning Waterfront Home on the Elk River in Locust Point! Welcome to 55 River Road, Elkton, MD 21921, offering beautiful Elk River views and approximately 2,200± sq. ft. of total living space. This 3-bedroom, 3 full bathroom home features an open floor plan with immediate water views upon entry. Interior highlights include crown molding, plantation shutters, luxury LVP flooring, and fresh paint throughout (currently in progress).The eat-in kitchen is complete with granite countertops, dining area, and all appliances included. Enjoy water views from the spacious living room with a sliding door leading to a newer composite deck and paver patio, ideal for outdoor entertaining.The primary bedroom offers an en-suite bath with tiled walk-in shower and custom shelving. The finished lower level includes a side entrance and provides flexible space for a home office, family room, or additional living area.Recent updates include a new Architectural Lifetime roof (2024), Gutters/Downspouts (2024) new propane HVAC system (2024), and new bulkhead (2021). Conveniently located near multiple marinas and a community boat ramp.

Welcome to your private oasis! This charming home boasts mature landscaping that provides both beauty and privacy on a large corner lot. Custom built Cape Cod offers a first floor primary suite, living room with fireplace and built ins, formal dining room and a kitchen with granite counters and updated appliances. There’s an open area on the 2nd level ideal for reading or watching TV. Plus 2 more bedrooms and an office. Updates include: new carpet primary BR, garage door 2024, roof Dec 2022. Enjoy the serene ambiance from the large deck, overlooking a picturesque pond with not one, but two enchanting waterfalls. The soothing sound of cascading water creates a tranquil atmosphere, perfect for relaxation and unwinding. This property is a true retreat, offering an idyllic escape right in your backyard. Located just minutes from the Chester River and Chestertown’s historic district.

Originally built in 1930. Completely updated and tastefully renovated. Perfect year round or seasonal cottage. In the very special private community of Kenmtore Park. Year round activities for all. Nightly get together at the Big Pier to capture the most beautiful sunsets on the Sassafras River. Morning coffee is served on the deck off of the kitchen. Invite friends over for a day at the beach then a casual dinner served on the secluded patio off the entertainment room. Great place also for a fire pit in the cooler months. All bedrooms are on the opposite side of the home from the entertainment room and the patio for convenient privacy. Walk to the beach or ride down on a golf car, there is always something to watch and usually someone to talk with. Kentmore is close to Galena on the North side. Visit the enchanting Cross Street Market and the Sassy market. Get take out from Twinnys or Galena Pizza. Upscale dining at the Kitty Knight or the Fish Whistle. Head South from Kentmore and come across Washington College and all the amenities of Historic Chestertown. Jump on your boat or hitch a ride on a neighbor's boat for a great day on the river. Boating, wakeboarding, skiing or tubing. Jet ski anyone? At night view the endless unobstructed sky and a million stars, planets, and the moon.

Impeccably maintained and thoughtfully upgraded, this custom-designed home is a true standout! Situated on over a half-acre just outside of town limits, this property offers the perfect blend of peace and convenience—within walking and biking distance to shopping, dining, and all the charm the town has to offer.Step inside to discover a warm, welcoming interior featuring gorgeous hardwood floors throughout, a main-level primary suite with a beautifully renovated bathroom including large double sink vanity and oversized tile walk-in shower, and a bright, open layout that effortlessly flows from room to room. The spacious living room is bathed in natural light from the newly replaced celestory window and sliding glass doors, creating a cheerful and inviting atmosphere. The dining area connects seamlessly to the stunning, newly renovated kitchen, where you'll find quartz countertops, a farmhouse sink, stainless steel appliances, and thoughtful storage. The split bedroom floor plan offers comfortable guest rooms or office space, while the partially finished basement is ideal for a rec room, workshop, gym, or creative studio—with tons of extra storage space. A dedicated laundry room and walk-in pantry add functionality and convenience to daily living.Outside, you'll enjoy the peaceful setting from the covered front porch, a long asphalt driveway, a detached two-car garage, and a charming gardening shed—perfect for tools, hobbies, or storage. The manicured lawn is low-maintenance and beautifully landscaped for year-round curb appeal.From 2021 to 2024, KRM Construction completed an extensive list of high-quality upgrades, including:2021: New roof, water conditioner, tankless propane water heater, new laundry room/pantry, and a heat pump with propane backup for temps 40° and below2022: Fully renovated kitchen and bathrooms2023: Replacement of celestory window and sliding glass doors to enhance light and views2024: New sump pump with battery backup for added peace of mindThis home has been lovingly maintained and thoughtfully improved for comfort, efficiency, and timeless style. It truly has it all—space, upgrades, location, and quality craftsmanship. Don’t miss this Eastern Shore beauty!

If you are looking for a beautifully designed Victorian home in a quaint waterfront small town with a marina, this is the one for you! This turn-key historical home has been thoughtfully designed with an Airbnb or vacation home use in mind, complete with custom decor and carefully selected antiques, to instantly transport you into another world. Only steps from the small town of Chesapeake City along the famous C&D Canal, you can enjoy the many town events, shops, cafe, waterfront restaurant, ice cream shop, marina, and more! This home has been carefully renovated to make it shine and have modern conveniences while maintaining its Victorian charm. The wrap-around front porch welcomes you to the home and features a plaque naming this the Barwick House circa 1850. Walking into the front door, you are greeted by the lovely foyer with a vestibule seating area. To the left of this is a living room with electric fireplace and beautiful mantle. The dining room has been opened to the kitchen which makes it a welcoming space to entertain. This room is a showpiece with exposed ceiling, dual chandeliers, large dining table, custom island and cabinetry utilizing antique furniture to take the charm to the next level! Off the kitchen is a laundry room, mudroom, and a sunroom which could also be used as a first floor bedroom or bonus room. There is also full bathroom with ADA walk-in shower and intricate detailing in the design with nods to the Maryland waterfront setting. The second floor has one of the best features of the house: the first bedroom not only has beautiful exposed beams, but it also features custom stairs up to a secret loft, perfect for a kids hide-out or reading nook, with railing hand-wrapped with nautical rope to create a magical getaway experience! This second floor has two more bedrooms, one with exposed beams & loft-style decor ledge and the other with double closets and built-in shelves, and the second full bathroom with clawfoot tub. The third floor has two bedrooms, one which has a beautiful feaux-fireplace mantle. There are 5 bedrooms total in this home, plus the bonus room/sunroom on the first floor, and 2 full bathrooms. Outside, you'll find a large deck to enjoy all summer long, as well as a spacious back yard - only a few blocks from the Marina! This property has convenient off-street parking for up to 6 cars in the back and there is permitted parking along the street. The mechanicals have also been updated for buyer's peace of mind, including New Roof 2023, New Electrical & Panels 2022-2023, New Wall Mini-Split Heating/Cooling 2022, added insulation, and much more! This is a one-of-a-kind gem that you will not want to miss!

There’s no place like home! Welcome to the Flyway neighborhood in Chestertown, where this 4 bedroom, 3.5 bath home offers a flexible layout with both formal and casual living spaces. The front entry opens to a formal dining room and a separate bonus room that can serve as a living room, playroom, or home office. The family room with propane fireplace flows into the eat-in kitchen that features a breakfast bar, pantry, and space for a table. Just off the kitchen is a half bathroom and interior access to the 2 car garage. Sliding glass doors lead to a composite deck with steps down to the spacious fenced backyard, all situated on a 1 acre lot offering space to enjoy outdoor living. Upstairs is the primary suite with two walk-in closets and a private bath with dual vanity and walk-in shower. A secondary suite includes its own private bath and walk-in closet, while two additional bedrooms share a hall bath. Laundry is conveniently located on the upper level. Recent updates include a new roof on the home and shed (2025) and recently replaced water heaters (downstairs in 2025, upstairs in 2019). Conveniently located just minutes from downtown Chestertown’s shops, restaurants, waterfront, and Washington College. Schedule your showing today!

Welcome HOME! This beautifully updated 4 Bedroom, 3 Full Bath Rancher with screened in porch, has been meticulously renovated over the past 4 years, nearly every detail has been refreshed!!Kitchen has been updated with freshly painted cabinetry, granite countertop with new sink, a trendy tile backsplash, and modern appliances, creating a clean, updated look. Bright and functional, this space blends style with everyday convenience, making it the heart of the home.Hardwood flooring has been replaced, the entire house has a fresh coat of neutral paint, new roof (2021), owned solar panels, Thompson Creek windows (2023) and sliders, washer/dryer, fridge, microwave, garage door, interior garage upgrades (flooring, panels), pellet stove, lighting, ceiling fans, and much more.The lower level offers 12ft high ceilings, a walk-out slider to the back yard, bedroom with full bath, large walk-in closet, and plenty of space for entertaining or potential in-law/apartment use. Large accessible storage area with plenty of shelving. Landscaping has been completely redone, giving the home a fresh, like-new feel.This stunning home is located just a few minutes from downtown North East!

Discover the charm and potential of this 3-bedroom, 2.5-bath home nestled on a peaceful parcel in Warwick, Maryland. Perfect for horse lovers—offering space to make your equestrian dreams a reality. While the home is in need of a little TLC, it offers a unique opportunity to add your personal touch and build equity. Surrounded by nature and tranquility, this property provides a welcome retreat from the hustle of daily life. 3 Spacious Bedrooms | 2.5 Baths Roof (2011) | HVAC (2014) | Water Conditioner (2024)Sold As-Is, Where-Is. Minutes to Delaware.

Welcome to your future home, a stunning residence nestled on a sprawling 1.5-acre lot, offering the perfect balance of comfort, privacy, and space. This impressive property boasts 5 generously sized bedrooms, each providing a peaceful retreat for family members or guests. With 3 full bathrooms, mornings and evenings are sure to run smoothly for everyone in the household. Step inside to discover a bright and open floor plan featuring inviting living areas filled with natural light. The large, modern kitchen was fully remodeled in 2022 with stainless steel appliances, white cabinetry, and handpicked quartz countertops, making it ideal for both everyday meals and entertaining. The dining area flows seamlessly into the spacious family room, where you can relax by the pellet stove or enjoy gatherings with loved ones.Outside, the expansive 1.5-acre grounds offer countless possibilities & was fully fenced in 2024 for an added piece of mind. Plenty of room for outdoor gatherings on the deck and space to play in the yard! The property also provides ample parking with a 3-car garage and an extended driveway. Recent updates include Pella windows throughout (2023) New carpet (2024) Downstairs bathroom remodeled (2023) Roof (2018) with a 50-year transferable warranty. Don’t miss the opportunity to make this remarkable property your own place where you can enjoy space, comfort, and the freedom to create your ideal lifestyle.

This newly constructed end-unit townhome at 300 Dixon Street offers a bright, spacious, and efficient four-level layout just a few blocks from downtown Easton. Finished in cream-colored Hardie Plank siding, the residence benefits from extra side windows that bathe the interior in natural light and a distinctive wrap-around porch—extending along both the front and side.Level 1 – Garage & Service:The ground level features a private garage with rear entry and direct access. This level also includes a half bath, a versatile bonus room, a dedicated laundry room, and a utility closet—ensuring everyday convenience and ample storage.Level 2 – Main Living Area:Step through a welcoming foyer into an open-concept space that seamlessly integrates the living room, a well-appointed kitchen, and an eat-in dining area. The kitchen is equipped with GE stainless steel appliances (cooktop, double wall oven, hood vent, dishwasher, refrigerator, and garbage disposal), complemented by upgraded quartz countertops and custom Timberlake cabinetry. Sliding glass doors lead to a balcony that fills the space with natural light, while a half bath, a coat closet, and a pantry round out the level. High ceilings, recessed lighting, and crown molding further enhance the inviting ambiance.Level 3 – Bedrooms & Full Bathrooms:Designed for comfort and privacy, the third level houses three bedrooms and two full bathrooms. Both full baths have been upgraded with quality Moen fixtures, glass shower doors, tile floors, quartz countertops, and custom Timberlake cabinetry, with white subway tiled showers. The primary bedroom suite features a generous walk-in closet and an expansive primary bathroom complete with a dual vanity and two storage closets for toiletries and linens. Carpeted bedrooms and hallways add a cozy touch throughout.Level 4 – Loft:The flexible loft, complete with its own mini split unit for heating and air conditioning, offers an adaptable space ideal for a home office, playroom, or additional living area. Abundant natural light makes this top level particularly inviting.Community & Location:Unit 201 is part of the Dixon Square Townhouses in Easton, located in Talbot County at the heart of Maryland’s Eastern Shore. The property is bordered by the nearly three-mile Easton Rails-to-Trails, offering recreational opportunities and convenient access to local shops, parks, and other destinations. Dixon Square itself features charming streetlights, brick stairways, sidewalks, and beautifully maintained landscaping managed by the HOA—making homeownership both enjoyable and low maintenance. Whether you’re drawn to outdoor adventures, the arts, festivals, or dining at a diverse mix of locally owned restaurants, this vibrant community provides endless opportunities to live your best life.

Historic charm with a modern floor plan. Live just around the corner walking to the shops, galleries, and restaurants of downtown Chestertown in this beautifully updated Victorian on quiet Mill Street. High end appliances such as Miele and Bosch adorn the kitchen and laundry. Easily converted back into a 3 bedroom. The backyard is well landscaped, has a covered outdoor living space, and a spacious detached hobby shed or office space. This low maintenance property with walkable lifestyle works perfectly for a weekend retreat or year round residence. Chestertown is located less than 1.5 hours from Washington D.C, Philadelphia, and Baltimore.

Step into this one‑of‑a‑kind Dutch Colonial—no cookie‑cutter here! Full of charm and character, this beautifully maintained home sits on 1.40 private acres, has been professionally painted throughout, and offers a layout that’s both spacious and versatile.The main level features beautiful hardwood floors, while the expansive 21’ x 21’ family room boasts luxury vinyl plank flooring, combining comfort and style. A cozy sitting room with a wood‑burning fireplace invites you to relax, and the dining area includes a sliding glass door to the covered rear porch—perfect for easy indoor‑outdoor living.The oversized 26’ x 13’ kitchen is a chef’s dream with a brand‑new center island cooktop, pickled cabinets, granite countertops, and a wall oven. Also on the main level is a flex room with a closet—ideal as a home office, guest space, or bonus room—along with a convenient powder room.Upstairs offers 3 spacious bedrooms, another room could be a bedroom, hardwood floors, and 2 full baths. The upper level is full of charm with deep window wells, and the entire home is complete with vinyl tilt windows—easy to clean and energy‑efficient. The primary suite includes a walk‑in closet and a bathroom with a large shower.The partially finished, walk‑out basement offers endless potential for additional living space, a rec room, or home gym. Step outside to a covered rear porch, then head down to your private inground pool and pool storage—an entertainer’s dream! A detached 2‑car garage (24’ x 22’) and a peaceful setting with no HOA complete the package.All this just minutes from I‑95, shopping, dining, and marinas—an ideal location for commuters or weekend adventurers!A must‑see to appreciate the amazing work done on this home… pure perfection!!!

FRESHLY PAINTED WHOLE EXTERIOR, GARAGE/IRON FENCING!!!!!! PHOTOS ARE GENERATED TO SHOW IDEAS!!! HOME IS CURRENTLY VACANT!!! Welcome to the Johnson-Lindsey House, a rare opportunity to own a piece of Chesapeake City’s history. Located in the heart of the Historic District, this Federal-style home was built around 1850 by Joseph W. Lindsey, the town’s sawmill and lumber yard owner. Zoned Village Center (VC), the property offers incredible flexibility for residential or commercial use, making it ideal for those looking to blend history with modern living or business potential. Situated along the route of Chesapeake City’s beloved parades and festivals, it’s just a short walk to waterfront dining, boutique shopping, and local attractions.This charming home exudes character with its classic wood-sided Federal-style architecture and distinctive bump-out picture windows on the south side. The original cast and wrought iron fence still encloses the front courtyard. The front entrance welcomes you with intact stained glass and an old-style door ringer, setting the tone for the timeless beauty within.Inside, the home showcases original hardwood flooring, tall wood windows with storm covers, and six-inch floor moldings. The light-filled foyer leads into a spacious family room with floor-to-ceiling windows and an electric fireplace wired for propane. From there, the dining room offers built-in cabinetry and access to a covered side porch. The remodeled kitchen seamlessly blends old-world charm with modern updates, featuring Quartz Silestone countertops, Italian subway tile, luxury vinyl plank flooring, a new sink, stainless steel appliances, and professionally painted cabinets. Off the kitchen, a remodeled powder room and an enclosed laundry room with an antique sink provide added convenience.The second level offers a generously sized primary suite with a fully remodeled bath, including a tile walk-in shower and luxury vinyl plank flooring. Two additional bedrooms on this floor provide space for guests, family, or a potential additional full bath if desired. The third level features another bedroom and another room currently used as storage, with ample space to add a third full bath.The backyard is a hidden retreat, offering a courtyard-style space with a side porch, a brick side patio, and a rear brick patio leading to the detached two-car garage. Very few homes in town offer garage parking, making this a rare and valuable feature. With electricity, a concrete floor, and a propane heating element, the garage could easily be transformed into a carriage house, Airbnb rental, or business space. A parking pad allows for two additional vehicles, making this property one of the few in the historic district with a backyard backing to woods and extra off-street parking.This home has been meticulously maintained with a series of updates, including five new mini-split heating and cooling units installed in 2024, along with a new storm door, professionally painted kitchen cabinets, and new ceiling fans. Recent improvements also include luxury vinyl plank flooring in the kitchen and primary bath, updated carpeting on the stairs and upper hallway, a new furnace, oil tank, and hot water heater, as well as professional interior painting. The main architectural shingle roof was replaced in 2019 with a 30-year warranty.The Johnson-Lindsey House has been featured on the Candlelight Tour and is prominently displayed on the cover of the Chesapeake City town map. Annual grant opportunities through the Maryland Historic Trust provide additional incentives for restoration and improvements. Whether you're looking for a distinctive home, a commercial opportunity, or a combination of both, this historic gem is truly one of a kind.

Welcome to your private Eastern Shore escape! Nestled on 8.36 tranquil acres just outside the charming waterfront town of Rock Hall and only 20 minutes from historic Chestertown, this beautifully updated property offers a rare blend of nature, comfort, and recreation. Surrounded by abundant wildlife, this property is a haven for hunters and nature lovers alike—ideal for deer, turkey, and waterfowl hunting right in your backyard. Birdwatchers will delight in the daily sightings of eagles, owls, and an array of coastal birds, while gardeners will appreciate the expansive space ready for planting, harvesting, and quiet reflection. Located just minutes from the Rock Hall Yacht Club and Lankford Bay Marina, and with easy access to the Chester River and the Chesapeake Bay, you're perfectly positioned to enjoy some of the region’s best boating, sailing, fishing, and crabbing. This is true Eastern Shore living at its finest. Inside, recent renovations bring modern comfort and style to this peaceful retreat. The kitchen has been completely updated with new windows, new cabinets, granite countertops, farmhouse sink, new stove and microwave, and new flooring and lighting. Ductless/mini-split units in all living areas ensure year-round climate control. The spacious family room has been expanded and remodeled to create an inviting space for gathering, with views of your wooded acreage just outside. The extension has new windows, rear door, and flooring. The downstairs bathroom has also been tastefully redone with a walk-in shower, updated flooring, and new fixtures. A new roof was completed in May 2025, offering peace of mind for years to come. A formal dining room offers flexibility—convert it into a main-level bedroom and pair it with the remodeled first-floor bath for convenient single-level living. Whether you're seeking a peaceful primary residence, a hunting lodge, or a getaway close to the water, this property has it all—scenic acreage, modern updates, and unbeatable access to the best of Maryland’s Eastern Shore. Don’t miss this opportunity to own your own piece of paradise just minutes from Rock Hall’s waterfront charm.

Spacious & Updated Home in Cloverfields on Kent IslandWelcome to this beautifully improved home located in the desirable Cloverfields community on Kent Island in Stevensville. Set on an oversized double lot with a private, tree-lined backyard with a brand-new privacy fence, this 3 bedroom, 2 bath home offers over 2,300 sq ft of total living space and a long list of recent upgrades.On the upper level, enjoy an open concept with laminate flooring throughout. An open kitchen with breakfast bar has all the appliances you need including dishwasher (one year old), stove (less than two years old) and a brand-new microwave. The dining room walks out to a screened in balcony to enjoy your morning coffee while catching the morning news or Today show. The living room features a large bay window allowing lots of natural light.The newly renovated primary suite features brand new luxury plank flooring, walk-in closet and beautifully renovated primary bath with soaking tub, double sinks and walk in shower. A second bedroom and second full bath round out the upper level rooms.On the lower level you'll find a generously sized third bedroom, large family room with fireplace that walks out to the fenced in yard, laundry area and workshop with access out to the driveway area. Rough in plumbing appears to be in place for an additional bathroom but buyers are responsible for their own due diligence to add 3rd bath.Major improvements include a new HVAC system, privacy fencing, and new siding and roof just completed at the end of October 2025.Cloverfields offers exceptional amenities: private beach on the Chester River, marina with boat ramp and rental slips, seasonal pool, playground, clubhouse, and low annual HOA fees. Conveniently located just minutes from the Chesapeake Bay Bridge, with easy access to Annapolis, Baltimore, and D.C.Owners are motivated— purchased in 2024 with plans to make this their dream home, a job transfer has prompted a quick sale. Don’t miss this opportunity to own in one of Kent Island’s most sought-after communities.

Easton Club East/Chesapeake by Del Webb. Popular one-story beautifully maintained Wittman model. Great room with gas fireplace, dining room, spacious gourmet kitchen with large center island and breakfast nook, granite countertops and stainless appliances. Office with built-in bookshelves, primary suite, guest bedroom and hall bath, sunroom with tile flooring overlooking patio with pergola. Separate laundry room with sink and overhead cabinets. 2 car rear loading garage and additional driveway parking. Mature landscaping with irrigation system. Roof (2020), HVAC (2015). This is an active 55+ community with many amenities. Clubhouse, outdoor pool, tennis/pickleball courts, Bocce ball, horseshoes, exercise paths, putting green and more. Close to downtown Easton, St. Michaels and Oxford and convenient commute to Maryland and Delaware beaches and the Western Shore.

Step onto the front porch and open the door to the home you have been waiting for! This Carriage Style home has been well-loved and well-maintained. Updated and renovated in 2019-2020 .There is a bonus room with barn doors that provides options for additional living space, also perfect for an office or playroom and there is convenient access to the fenced yard with patio and a separate fenced area for the pup!The First floor private primary bedroom has custom updated bath by Paquin Design Build, with a separate tub and walk-in shower.The Kitchen features granite counter tops , stainless appliances, bar seating as well as table space overlooking a 2 story family room with a soaring ceiling.There's also the separate dining room (or flex room) and a powder room for guests. New Roof 2020. The second floor offers 2 more bedrooms and a second full bath. Whole House Generax generator for peace of mind.…in desirable Clayborne Woods in Chester!

This is the one you’ve been waiting for! With over 2,100 square feet of living space, this 4-bedroom, 2-bath home sits on a spacious half-acre lot and has all the room you need—inside and out. The layout is so functional, with three bedrooms and a full bath on the main level, plus an XL living room with a cozy gas fireplace and loads of natural light.The real showstopper? The entire second floor is dedicated to the primary suite—your own private retreat! You'll love the large bathroom, walk-in closets, and the Juliet porch with gorgeous views... it’s like a breath of fresh air every single morning.There’s even more to love outside—fire up the grill and enjoy the deck and outdoor entertaining space. And if you’ve been dreaming of a workshop, gym, or storage for all the toys, you’ll flip for the 30x40 pole barn out back. Still need more? The house also has an attached garage and a separate laundry room tucked away for convenience.This one checks all the boxes—and then some. Come see it for yourself!

Price improvement! Located in Country Club Estates, on a lovely, corner lot with mature trees. Solid brick rancher with good bones. 3 bedrooms, 2 full baths. The basement has a workshop space and garage. Hardwood floors. Spacious family room with woodstove. Nice screened-in porch and outdoor patio with a fire pit. Home is ready for your finishing touches. Near the Chester River Yacht and Country Club and just a few minutes to historic downtown Chestertown.

Lovely countryside Cape Cod on over 3 private acres. Sit on the front porch and enjoy the summer breeze or grill off the back deck and watch the deer in the woods. This home has been meticulously cared for and features a first floor primary bedroom with walk-in closet and ensuite bath with a massive ceramic tile shower. Large formal living room with brick fireplace flows into the kitchen / dining room combo behind with sun-room and back deck. Recent upgrades include: crawl space encapsulation, stainless steel kitchen appliances, downstairs heat pump, backyard fence, solid wood plantation shutters, automatic retractable blinds and more. Quick drive to historic downtown Chestertown. Founded in 1706, Chestertown sits on the banks of the Chester and is home to Washington College. Enjoy the historic homes, local shopping, restaurants, art galleries, and waterfront parks. Chestertown is home to many festivals, an award-winning weekly Farmer's Market, and a brand new YMCA. Enjoy easy country living on the Eastern Shore.

Back on the market at no fault of seller. Rigbie Bluff is the perfect maintenance-free community in the quiet waterfront town of Betterton; known as the Jewel of the Chesapeake. Located at the confluence of the Sassafras River and Chesapeake Bay, Betterton got its reputation for its picturesque sunsets and wonderful public beach. Embrace the waterfront lifestyle and so much more without the waterfront taxes. This 3 bedroom, 2 bathroom unit is being sold fully furnished and with a deep water boat slip, boat lift and jet-ski lift. As one of the larger units; it has plenty of room for the whole family. Natural light abounds with water views from both balconies or anywhere inside. Galley kitchen with granite countertops and stainless steel appliances. The main floor has an open floor plan, two bedrooms and a full bathroom. Large primary bedroom with ensuite bath and office space upstairs. Plenty of closet space throughout. Full basement has plenty of room for storing outdoor toys and equipment. Recent upgrades include: primary bathroom remodel, waterproof luxury vinyl plank flooring (original hardwoods underneath), carpets, Anderson windows, washer/dryer, water heater, interior doors, paint, and much more. Condo Association just finished renovating the decks and siding. Condo amenities include: private pier with water and electric, designated boat slip with 6,000 pound lift, community pool and kayak storage. Just a few steps from the water. This is the perfect weekend getaway or primary residence on the Eastern shore. Come see all that the Jewel of the Chesapeake has to offer.

Fantastic Opportunity to own over 23 acres in northern Calvert County. This property is a rare combination of a private rural setting with easy city access to D.C., Annapolis or Andrews Air Force Base. Rolling farmland adjacent to dense wooded areas create a scene environment for a homestead. Recently built 40' x 70' two level metal pole barn is currently used for farm equipment storage but could be upgraded. Currently only agriculture operations. Farm and Forest District Zoning allows some commercial uses.

NEW ROOF -- NEW CARPET-- ALL NEW INSULATION AND FLOOR VAPOR BARRIER IN CRAWL SPACE-- NEW PAINT IN UPSTAIRS HALL, STAIR WAY , FOYER, KITCHEN AND FAMILY ROOM !!Welcome to 29184 Corbin Parkway located in Easton Maryland. Colonial offering a lovely sunroom with tray ceiling and tile floors and door to the back patio. Family room with gas fireplace. Kitchen with sile stone counter tops. The master suite/bath with soaking tub and separate shower. Two additional bedrooms and bath on second floor.Nice two car garage with area for workshop-- carpet and overhead lighting. Enjoy your evenings relaxing on your back patio and watching wildlife. Beautiful flower beds in back the front yards. Invisible Fence front and back yards. All you need for this to be your home is your Family and belongings

Discover this spacious home offering 3,100 sq ft of living space on a ½ acre lot with deeded access to the Chester River. Generously sized rooms and an inviting floor plan create an ideal setting for both everyday living and entertaining. The main level bedroom features a recently remodeled bath and large walk in closet. Enjoy the natural light and tranquil views from the sunroom, perfect for relaxing year-round.*New roof has been installed!

Are you looking for a historic farm home with modern charm and Acreage? .5.03 acres to be exact! This home was originally built in the 1700's and is situated in picturesque rural Frederica. It's the perfect location for a mini farm, already set up with a small stable and barn. This home also features a 1st floor primary, 3 additional bedrooms upstairs and a recently upgraded kitchen. This unique home has endless possibilities. Make sure to put this one on your must see list. Seller is Motivated!!

Experience the best of in-town Chestertown living in this custom-built single-level home! The open floor plan features abundant natural light, gleaming hardwood floors and a bright, inviting layout perfect for entertaining or relaxing. The dining room is open to the kitchen which includes some updated appliances, ample cabinet storage, and a breakfast bar. The primary suite has a large walk-in closet and an en-suite bath which now boasts a soaking tub. Step outside to enjoy the large deck, fire pit patio, and fully fenced backyard. This home offers comfort and convenience at every turn. Just a few blocks from Washington College and a short stroll to Downtown Chestertown’s charming restaurants, shops, and waterfront.

Fully furnished! Adorable rancher in a PRIME location in Rock Hall. Just steps to the marinas, restaurants, and shops. The house has been completely remodeled. All new appliances. Large family room with a pellet stove and plenty of space for social gatherings. Nice-sized bedrooms and 2 full bathrooms. Luxury vinyl plank flooring throughout. Detached garage and potting shed. Less than 1/2 mile to the public beach. Private backyard with koi pond and water feature. The current owners have their boat docked at a nearby slip, and they can see it from the property. There is no work to be done here. Just bring a suitcase and move right in!

GREAT NEW PRICE!Why wait for new construction when this practically brand-new home is move-in ready? 4 Bedrooms 2.5 Bathrooms 2-Car Garage. Located in the sought-after Ridgely Forest community! Step inside to an open floor plan featuring stunning vinyl plank flooring on the main level and fresh paint throughout. Cozy up around the shiplap fireplace centerpiece—perfect for entertaining! The main level offers a versatile space ideal for a home office or guest bedroom. Upstairs, enjoy the convenience of second-floor laundry and spacious bedrooms with plush carpeting. The primary suite boasts a gorgeous accent wall, a large walk-in closet, and a beautiful ensuite bathroom. Your backyard oasis awaits—just add your personal touches to make it your own. The unfinished basement offers endless possibilities for additional living or recreation space. Entertain with ease in the kitchen that opens seamlessly to your living and dining areas—perfect for hosting friends and family! Don't miss this opportunity to own a stunning home in a fantastic location—schedule your showing today!

Welcome to this beautiful, turn key home situated peacefully in a country setting between Easton and Oxford! No stone left unturned with the masterful finishes that present a modern farmhouse appeal. Everything has been updated in 2025, including a brand new well and BAT septic system, HVAC, roof, and windows. Surrounded by gorgeous, tranquil farmland, you will find yourself with easy access and minutes from Oxford, Easton, and the beaches. Very private setting with .8 acres, a covered concrete carport and plenty of room for more. Call today for your private showing! Owner is a licensed Real Estate agent.

Ranch Home in Dogwood Village. Welcome to this stunning move-in ready ranch home located in the heart of Galena’s desirable Dogwood Village. Offering 2,587± square feet of TOTAL living space, this property combines modern updates with small-town charm. Inside, cathedral ceilings with skylights in both the gathering room and primary bedroom create a bright, open, and airy atmosphere. The open-concept kitchen and living room are connected by a quartz island breakfast bar, designed for both everyday living and entertaining. New waterproof luxury vinyl plank flooring has been installed in the foyer, kitchen, living room, and primary suite. The primary suite also features a spa-inspired bath with a custom ceramic tile shower. A spacious finished basement provides a large family room, a separate office space, and abundant unfinished storage. Additional peace of mind comes with a brand-new HVAC system. The property is situated on .26 acres with public utilities and backs directly to the town park, which offers a walking trail, playground, and pavilion. A stamped concrete patio provides the perfect outdoor setting for dining, movie nights under the stars, or enjoying live music from Galena’s annual Dogwood Festival. The location is ideal, just a short walk to Galena Pizzeria, the library, Cut Loose Salon, Cross Street Market, and more. This home truly has it all—style, space, and a prime location in the heart of Galena.

Charming & Spacious Home in Easton, MD – Backs to Woods!Welcome to 29296 Corbin Pkwy., Easton, MD 21601 – a beautifully updated 4-bedroom, 2.5-bath home offering modern comfort and a serene natural backdrop. Designed with an open floor plan, this home is perfect for both relaxation and entertaining.Step into a stylish kitchen featuring granite countertops, stainless steel appliances, a brand-new refrigerator and dishwasher, ample cabinet space, and a center island. Luxury flooring flows seamlessly throughout the home, enhancing its contemporary appeal. A new HVAC, a Washer and Dryer, and a Hot Water heater are also included.Enjoy outdoor living on the spacious back deck, perfect for gatherings or peaceful mornings overlooking the beautiful, expanded backyard. The property also includes two storage sheds, providing plenty of space for tools, hobbies, or extra storage.With generous living spaces, modern finishes, and a private setting backing up to the woods, this home is a rare find in Easton. Don’t miss the opportunity to make it yours—schedule your showing today!

Spacious One-Level Living Near Downtown Chestertown & The Chester River!Welcome to this beautiful 3-bedroom, 2.5-bath home offering 1,850 sq ft of single-level living on nearly a half-acre (.46 acres) in Queen Anne’s County. Ideally located just minutes from historic downtown Chestertown and The Chester River, this property blends convenience with comfort.Step inside to find a bright, open floor plan featuring vaulted ceilings with skylights, a cozy gas fireplace, and gleaming hardwood floors throughout. The bonus room off the living area makes a perfect home office, den, or playroom.The spacious kitchen offers a pantry and ample storage, while the large utility room and numerous closets provide excellent organization options. Generously sized bathrooms add to the home’s comfort, and the oversized garage gives you plenty of room for vehicles, tools, or hobbies.Enjoy the privacy of your nearly half-acre lot, all while being close to charming shops, restaurants, marinas, and community events.This home is move-in ready and designed for easy living — a desirable find near The Chester River!

Like New- Only used part-time **Welcome to 500 Regulator Drive South, a beautifully maintained, like-new Roosevelt model by Gemcraft Homes, offering modern comfort, thoughtful design, and access to one of Cambridge’s most convenient communities. As you enter, you’ll appreciate the inviting foyer that opens to a flowing main level designed for both everyday living and entertaining. The living and dining rooms set an elegant tone, while the family room, filled with natural light, offers a comfortable gathering space. The upgraded kitchen features granite countertops, stainless steel appliances, a large island, and an open layout that connects seamlessly to the optional sunroom, perfect for enjoying morning coffee or quiet afternoons. A half bath and access to the two-car garage complete this level, along with upgraded luxury vinyl plank flooring throughout for a cohesive, modern look. Upstairs, you’ll find a versatile loft area ideal for reading, hobbies, or a home office. The spacious primary suite provides a peaceful retreat, with two large walk-in closets and a beautifully upgraded Roman bath featuring a soaking tub, separate shower, and double vanity. Two additional bedrooms share a well-appointed full bathroom, and the convenient upper-level laundry room makes daily living easier. This home also includes a thoughtfully designed stone front exterior, upgraded roof, and a well-maintained yard on a quarter-acre lot. The community offers access to a private boat ramp and pier, making it easy to enjoy the Choptank River and all the natural beauty of the Eastern Shore. Located just minutes from the shops, restaurants, and conveniences of downtown Cambridge, 500 Regulator Drive South offers the comfort of a modern home in a location that perfectly balances lifestyle and leisure. You owe it to yourself to see this one in person. Schedule your showing today and discover all that this home and community have to offer.

Pride in Ownership! Amazingly maintained rancher offering one-level living with open floor plan. Chill on your front porch looking out on the fields that make this area so special. Or relax on the new huge back deck while you grill or pick crabs with family and friends. This quiet setting is removed from the hustle and bustle of daily life, yet close to highway access points to DE and the Bay Bridge with easy hop on/hop off of Rte 404.Updated bathrooms with an ample-size tiled primary walk-in shower that you can party in or just meditate and relax in. The massive flat yard gives plenty of opportunities for all types of enthusiastic hobbyists and professionals to use.

Looking for Brand New and the Simple Pleasures of One Level Living??? Look No Further! This charming rancher, nestled on 1/2+ acre corner lot offers the perfect blend of beauty, comfort and convenience. As you approach, you'll be greeted by a front porch that's perfect for relaxing, while enjoying your morning coffee. Step inside and you will see a well-designed open floor layout with beautiful LVP flooring and cathedral ceiling, a stylish kitchen boasting SS appliances and an island/breakfast bar, a spacious living room and an adjoining dining area adorned with 8 ft slider that floods the space with tons of natural light and creates a seamless connection to the outdoors. The sleeping zone features a primary bedroom with an ensuite bathroom and a walk-in closet, there's also two additional comfortable size bedrooms with a shared full bathroom. Additional highlights include designer lighting, quartz countertops, 8 ft front entry wood door, separate laundry/mudroom. large back deck for summertime BBQ's and entertainment. Just 2 blocks to the Chester River and the public boat ramp. Within close proximity to shopping, dining and the delights of downtown Chestertown... Easy access to Route 301...20 minutes to Delaware...30 minutes to Bay Bridge...Don't miss this opportunity to love where you live!! Quality Built (MHBR #3423).

Escape to the tranquility of rural living with this delightful 3 bedroom, 2 bath property nestled on a sprawling 1-acre parcel. Located in the heart of the countryside, this inviting home is ideal for a permanent home or as a second home to enjoy everything the Eastern Shore of Maryland has to offer, such as hunting, fishing, boating, or just a peaceful getaway. The vaulted living area is spacious and accented by a wood stove that provides both a cozy ambiance and efficient heating during colder months. The living room opens to a new 2-level outdoor deck, as well as the kitchen, perfect for entertaining family and friends. The large kitchen has an overabundance of new granite countertops, plenty of cabinets, and an island. The perfect kitchen for multiple cooks, and maybe an even larger island! The laundry room is located directly off the kitchen with access to the back yard, and to the garage. Perfect for extra storage or as a mudroom. The home features three nice sized bedrooms, including a primary suite with a full bathroom and dual closets. The property has plenty of room for a garden, boat or RV storage, or just sit back and enjoy the serenity of country living. Located just 1.5 miles from Route 301, the location is perfect for commuting north to Wilmington or Philadelphia, or head south to Annapolis and Washington DC.

This meticulously maintained end-unit townhouse offers the best of both comfort and convenience. Overlooking a scenic walking trail, this home is just a short stroll to Easton’s vibrant downtown, with dining, shopping, and all town amenities right at your doorstep. Inside, you’ll find gleaming hardwood floors throughout the main level, creating a warm and inviting atmosphere. The spacious living and dining areas flow seamlessly into a gourmet kitchen, complete with a double wall oven, gas cooktop, pantry, and elegant granite countertops. French doors lead to a outdoor balcony, perfect for relaxing or entertaining.The main suite is a true retreat, featuring a vaulted ceiling, loft area, a generous walk-in closet, and an en suite bath. The second bedroom also has its own walk-in closet and full bath creating a second main bedroom. Please note: this unit offers the same square footage as the 3-bedroom models, but the seller thoughtfully combined the two smaller bedrooms to create a spacious second primary bedroom instead. The lower level offers a cozy family room, laundry area, and a convenient half bath. Access to the 2-car garage is also located on this level. New roof and carpet installed 2025. Experience the charm of downtown living with the added benefit of modern comforts.

Beautiful Stone 1 1/2 story home with full basement. Hardwood floors under carpet. Enclosed Breezeway 13x10, w/updated windows and doors, to attached garage. Flagstone patio to the rear of home, off kitchen and dining room, leading onto level rear yard. This home is wonderfully located with the Susquehanna River and State Park at the end of Lapidum Road with a boat launching area and parking spaces - Really lovely and peaceful. Generac whole house generator. Furnace replaced approximately 2 years ago. Central A/C on maim first floor; Window Units 2nd floor.

JUST INSTALLED BRAND NEW CARPET!Welcome to 907 N Meadowview Drive, a beautifully maintained home in the sought-after Crestview community of Chestertown. Situated on a spacious .707-acre lot, this 3-bedroom, 2.5-bath home offers 1,842 square feet of comfortable living space.Step inside to find a bright and inviting living room anchored by a cozy pellet stove, ideal for chilly evenings. The eat-in kitchen provides plenty of space for casual dining, while the formal dining room offers flexibility—use it as a traditional dining area, home office, or playroom to suit your lifestyle.All three bedrooms are located on the second level, along with two full bathrooms. A convenient half bath is located just off the main living area, and a dedicated laundry room adds to the home’s practical layout. The attached two-car garage offers additional storage and convenience.Enjoy the outdoors with a private back deck, patio area, and two large side yards surrounded by beautiful landscaping—ideal for entertaining, gardening, or simply unwinding after a long day.Don’t miss your opportunity to own a well-cared-for home on a generously sized lot in a lovely neighborhood just minutes from downtown Chestertown.