A Rare Opportunity in the Heart of Historic ChestertownDiscover a truly special offering in the vibrant core of Chestertown’s Historic and Arts & Entertainment Districts. Owned by the same family for over 50 years, this multi-family property sits on a generous double lot known historically as the Laurence Lots—featured on original town maps and steeped in local heritage.Brimming with character and potential, the property currently features a townhouse on one side and two apartments on the other, offering a flexible layout ideal for renovation, income generation, or a creative reimagining. Whether you're envisioning a stately single-family residence, a dynamic live/work space, or a thoughtfully restored multi-unit investment, the possibilities are as expansive as the lot itself.That said, this is not a turnkey property. Significant settling has occurred over the years, and a substantial renovation will be required to bring it back to life. Offered strictly as-is, this is a true fixer-upper for the visionary buyer ready to take on a transformative project.Situated within both the Arts & Entertainment District and Enterprise Zone, this location supports both residential and business uses—making it an ideal candidate for those looking to merge lifestyle, business, and history.Bring your vision, creativity, and tools—and seize the chance to breathe new life into a piece of Chestertown’s storied past. Opportunities like this don’t come along often.Schedule your showing today and imagine the future you can build here.**See updated zoning info from the town in documents

One parcel comprised of 2 cleared lots in Tolchester Estates. The community is on the Chesapeake Bay and the residents have access to the beach and there is a marina close by.County states water/sewer allocation is available. Buyer to confirm with due diligence.

18th century historic home in downtown Chestertown with a separate carriage house! The main home features 3 bedrooms all with en-suite baths. The carriage house has an additional 2 bedrooms and 2 baths with separate laundry and a brick patio. Entrances to the property from Queen St. and Horsey Lane, 2 driveways with plenty of parking spaces. Original wood flooring throughout much of the house. The first floor features a living room, dining room, kitchen, and half bath. New owner to add vanity and toilet to one of the upstairs baths. Second-floor laundry room. Lovely landscaping and fenced-in yard between the main house and the carriage house. Just a short walk to the heart of downtown Chestertown. Definitely a rare find.

Welcome to this charming and elegant 2 bedroom, 2.5 bathroom condo nestled in a tranquil water-oriented community near the Chester River in the historic town of Chestertown, Maryland.This gorgeous home is situated in a prime location, offering easy access to nearby shops, cafes, and restaurants. As you step inside, you'll be greeted by a warm and inviting atmosphere that seamlessly blends classic charm with modern convenience.On the main level , you'll find access from the attached garage or front porch. Off the spacious hallway you have the enclosed Washer/Dryer unit, storage closet and full bathroom. French Doors leading to the first floor study with a bedroom to the left and straight ahead to the downstairs screened in porch overlooking the serene community pond.The upper level features an open-concept living area that's perfect for entertaining. You'll love the spacious kitchen with its stainless steel appliances, sleek countertops, and ample cabinet space. The dining area is flooded with natural light, creating the perfect ambiance for family meals and gatherings with friends. Enter the upstairs porch overlooking the pond with views of the pond, this is true indoor/outdoor entertaining.The upstairs primary suite is a true retreat, complete with a luxurious en-suite bathroom featuring double sinks, shower and stunning finishes. A huge walk in closet completes this experience.This home is also ideally situated within a water-oriented community, providing easy access to boating, fishing, and other water activities. The community offers a dock, boat ramp, as well as grilling areas and a swimming pool for your enjoyment.With its stunning finishes, prime location, and luxurious amenities, this 2 bedroom, 2.5 bathroom condo is the perfect place to call home. Don't miss your chance to experience the best that Chestertown has to offer!

Sprawling brick rancher in a lovely, peaceful setting. Over 2800 sq ft. Large rooms with lots of natural light. Huge family room with cathedral ceilings and fireplace overlooking the ample rear yard. Formal living and dining rooms with hardwood floors and crown molding. HVAC is only one year old. New well pump and WIFI controlled garage door. Water heater new in 2017. Home has a grand, palatial feel with relaxing views from all the windows. Close to Chestertown and a golf cart ride to the Chester River Yacht and Country Club. High speed internet available on site.

A delightful 2 bedroom 1 bath Duplex Condo in the lovely Riverside Terrace community. The unit has been well-maintained and has breathtaking water views from the front yard and both upper and lower decks. Nestled in the heart of Historic Chestertown with easy access to town, the river, shops, Washington College, and hospital. Enjoy the beautiful tree-lined streets of this colonial-era town, the Saturday farmers' market, local theater and everything that Chestertown has to offer.

This sprawling brick rancher will take your breath away! Renovated top to bottom with updated systems, brand new stylish kitchen, luxury bathrooms, rich hardwood flooring, and a fabulous rear patio set on a large deep lot with mature trees. Single floor living with low maintenance ALL BRICK exterior, a 1 car attached garage and plenty of space for the entire gang! Minutes from Rt. 301 and commuting/shopping in Delaware, all set in a picturesque quiet small town with playground park just down the street. RECENTLY REDUCED! Come check it out today before someone else does!

Beautiful, well maintained 3 bedroom end unit townhome. Just minutes from downtown Chestertown. Features freshly refinished hardwood floors, new carpet, new roof, vaulted master bedroom, soaking tub and separate shower in the master bath, 9 foot ceilings on the first floor, walk out second story deck, and an over-sized garage with a workshop. The home is very close to shopping and restaurants. A perfect place for weekends or year-round lifestyle living.

Lovely cottage in Byford Heights, convenient location that's just minutes from the local hospital, shopping and schools. This mid-century home is move-in ready and you can take your time updating as you like...or keep it in it's current mid-century style. With 4 bedrooms and 2 full baths, there is plenty of room for a growing family. Hardwood floors throughout. Attached garage with a nice driveway provides ample parking. Large fenced in back yard with storage shed. Come see this lovely home today!

Just a few blocks away from the heart of downtown Chestertown, this bungalow could be your perfect home, or great investment property. With a large kitchen and dining room for entertaining and a living room with an abundance of natural light, this could be your happy place. The bedrooms are large, one with a half bath attached and the laundry/mud room has plenty of room for storage with a closet and cabinets.

Quiet Community, public water access block away, walking trail, Sunrise and sunset water views. Private fencing on one side, fencing for dogs in back yard. New Patio great for fire pit. Inside new wooden blinds, new luxury vinyl floor, new ceiling fan in living room, new gas stove. TAX free shopping in Middletown Delaware 15 minutes away. This is a very nice duplex.

Welcome to country living! This is a beautiful brick rancher in a beautiful country setting. Enjoy the peace and quiet of the surrounding Kent County farmland. Enjoy the beautiful Hardwood floors and natural colors as you walk through the front door. You will love the rear screened in porch, looking out over the trees and shrubs of Angelica Nurseries. Almost 1 acre of land for you to spread out on. You can stop over to Crow Vineyard and Winery and enjoy the winery and grass fed beef! You are close to Delaware and Tax Free Shopping , close to the water was well, stop down to Turner's Creek Park and Boat Ramp. Lots to do in the area for sure!

Priced To Sell Fast! Charming 2 Level Colonial, Spacious Kitchen with QUARTZ Counters, Stainless Steel Appliances, Modern Tile Backsplash, Spacious Bedrooms, New Custom Paint, Updated Bathroom, Brand New HVAC, New Flooring, Updated Lighting, Driveway, Much More!! Close to Schools, Shopping and Commuter Routes. This Will Not Last!

Lovely well-cared for home in the center of Kennedyville. 3br, 1.5ba 2 story home with large fenced in yard. New roof and flooring installed in 2019. Freshly painted and move-in ready! Should go for any financing type. Easy access to Delaware and points north. Minutes from Chestertown.

1600 SF 3 BR/2.5 BA home that shows like new located in the Village at Kennedyville offers a front porch that overlooks the community pond...full basement and garage...hardwood flooring on the first floor, beautiful cabinetry with a very spacious kitchen pantry

Great opportunity to own a lot in Chesapeake Landing! Currently does not have a valid perc. Water access to Worton Creek if you join the voluntary civic association! Close to Worton Marina and Chestertown.

Price Improvement! Spectacular waterfront on the Chester River!! Words can't describe the uniqueness of this property. With the historic charm of an older home but high end modern upgrades, you will be living the life of luxury. Spacious rooms, magnificent views of the Chester River and your private dock with new boat lift, sandy beach, and stunning new saltwater pool. Exposed beams, scalamandre wallpaper, and multiple fireplaces. First floor owners suite featuring reclaimed pine flooring, private laundry area, walk-in closet, gas fireplace and remodeled bath with soaking tub. Second floor owner's suite with additional laundry area and remodeled bath. Breezeway to the garage. New irrigation system to all flower beds. New paint inside and out. House has had major remodels in 2000 and 2020. Town sewer. Not far from town, but the property has a private feel. Come and be amazed!!

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.

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 masterpiece is finally complete. Rebuilt in 1863, the Tilley Residence showcases classic Second Empire style on one of Chestertown’s most prominent corners, neighboring Widehall and the Custom House.Expertly restored in 2024–2025 by one of Kent County’s premier builders, the home offers new HVAC, electrical, plumbing, roofing, flooring, and a refreshed open layout. Custom kitchen and baths balance modern comfort with timeless character. A grand three-story staircase and arched entryways welcome you inside. The front porch overlooks town and offers water views. The primary suite includes a fireplace, walk-in closet, and a tiled shower room with views from two sides. The Mansard roof provides a full third floor, and the basement includes a great wine cellar opportunity plus ample storage. A fenced rear yard, off-street parking, and a detached garage complete this rare offering—historic charm blended with modern amenities.

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.

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 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. Much more info and professional photos coming soon. Stay tuned!

Rare lake front property in Kent County! Welcome to your serene getaway nestled on 2.62 acres of partially wooded land on Urieville Lake! This stunning 4-bedroom, 3.5-bathroom home offers the perfect blend of comfort and privacy, making it an ideal retreat for families and nature enthusiasts alike. With an option of a first floor bedroom there are currently three bedrooms on the second floor and one bedroom in the walk out basement, there’s plenty of space for family and guests. The open-concept living area is perfect for gatherings, featuring ample natural light and gorgeous views of the surrounding landscape & lake! Enjoy convenience and comfort with two full bathrooms on the second, one full bath on the lower level and an additional half bath on the first, designed with modern fixtures and finishes. The finished walk-out basement provides excellent additional living space, bath/bedroom & perfect for a game room, entertainment area, or a private office. It also offers direct access to the beautiful outdoors. The property spans 2.62 acres, providing ample room for outdoor activities, gardening, or simply unwinding in nature. The partially wooded area enhances your privacy while allowing for serene nature walks right in your backyard & along the Lakes edge! Located on Urieville Lake, enjoy fishing, boating, kayaking and other recreational activities just moments from your doorstep. This private setting is perfect for those looking to escape the hustle and bustle of city life. Urieville Lake is about 35 acres in size and is shaped like the letter Y. The average depth is about 3 feet and supports a standard bass/bluegill fishery and is managed accordingly. Anglers may also occasionally catch other species including pumpkinseed sunfish, brown bullhead catfish, golden shiners and common carp. Welcome home!

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.

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!

OPEN HOUSE SCHEDULED FOR SUNDAY 10/12/25 HAS BEEN CANCELLED DUE TO POTENTIAL WEATHER ALERTS. PLEASE JOIN US NEXT SATURDAY 10/18/25 FROM 11:00AMTO 1:00PM.Discover Your Dream Oasis!Welcome to this magnificent 2,042 sq. ft. home nestled on a sprawling 1.72-acre park-like setting, where tranquility meets luxury living. The 20,000-gallon in-ground saltwater pool, complete with maintenance free decking and a liner replaced in the fall of 2022, serves as the centerpiece of outdoor enjoyment. Imagine summer days spent poolside in your personal paradise!Over the past two years, this home has seen numerous upgrades that enhance its value and comfort. A brand-new septic system (2023) and well pressure tank ensure reliability and peace of mind. The attached two-car garage features a new door with epoxy flooring that is both stylish and easy to maintain. Inside, enjoy a refreshed hall bath with a new shower and flooring, fresh paint, and new lighting. New outdoor rear awnings were installed to provide generous shade over the poolside deck areas.Step inside to discover a spacious open floor plan perfect for family gatherings. The large kitchen boasts all-new appliances, a massive island, ample counter space, and plenty of cabinets to make this kitchen a culinary enthusiast’s dream. The inviting living room features a pellet stove fireplace insert, while the adjacent all-season room offers seamless access to the pool and deck area, blending indoor and outdoor living effortlessly.The primary suite is a private sanctuary, complete with a cozy sitting area, a luxurious en-suite bathroom, a generous walk-in closet, and exclusive access to a serene concrete deck by the pool — an ideal spot for a hot tub!In addition to the main house, the property includes a two-story detached garage with electric and water access, perfect for a workshop or lounge area. It even has its own separate driveway! Two additional sheds provide convenient storage for lawn and pool equipment. A chicken coop is located by the detached garage..chickens can be included!This exceptional property backs onto a wonderfully wooded area, enhancing your privacy. Once overgrown, this space has been thoughtfully cleared to create a serene retreat. With plenty of room for future additions like a pole barn, the possibilities are endless.The property is conveniently located off Route 1 for easy commuting, minutes from Bayhealth hospital, and only 23 miles from Rehobeth Beach! Do not miss the opportunity to own this stunning home, designed for both relaxation and entertaining. Schedule your private tour today and experience the perfect blend of modern upgrades and natural beauty!

Welcome to 103 Landing Lane: a meticulously maintained 2-bedroom townhome in the desirable waterfront community of Chester River Landing. Just a short walk or bike ride into downtown Chestertown, this elegant, turn-key home offers maintenance-free living, great amenities, and easy water access to the Chester River. The welcoming foyer seamlessly flows into the rear den or office which could be converted into a 3rd bedroom. Off the den is the first-floor bedroom and full bath. Enjoy the summer breeze from the private back screened-in porch; recently upgraded with high-tech flex screens and a ceiling waterproofing, keeping the porch dry. The real action is found upstairs. The living room – anchored by an electric fireplace with stone surround – is complemented by the oversized second story deck; perfect for grilling or watching picturesque Chester River sunsets. The modern kitchen features new stainless-steel appliances, abundant cabinet space, granite countertops and a large island with breakfast bar. Plenty of space for formal or casual dining. The second floor is finished by an oversized primary bedroom with ensuite bath and large walk-in closet. Should one desire an elevator; there are two locations where one could be built into the existing design. Leave your worries aside as the condo association takes care of all exterior maintenance, yardwork, and repairs. Boaters will enjoy the well-maintained community dock with slips available for purchase or lease (with board approval), or just drop in a kayak or paddle board, great on warm summer evenings. Other community amenities include the pool, walking paths, garden, picnic and grilling areas, and a fire pit. Founded in 1706, Chestertown sits on the banks of the Chester River and is home to Washington College. Enjoy the historic architecture, local shopping, restaurants, art galleries, and waterfront walkways and parks. Chestertown is home to many festivals and an award-winning Farmer's Market every Saturday. New YMCA with full gym, racquet sports, lap pool, sauna, etc. Don’t miss your opportunity to enjoy worry-free living along the Chester River.

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!

Welcome home to this move-in ready home featuring 4 bedrooms and 3 full baths. The upper level features a large light-filled living room with windows on the front and side of the home. The living room opens into the combined kitchen and dining area. The kitchen features a new backsplash, stainless steel appliances, new faucet, and a kitchen island perfect for food prep, serving area, and plenty of additional cabinet storage underneath. The adjoining dining area provides ample space for your dining needs and offers convenient access to the nice-sized deck, perfect for outdoor dining and barbecuing. The deck has steps down to the rear yard for all of your outdoor activities. The partially fenced rear yard could easily be enclosed to provide safety and privacy. The remaining upper level features the upper level primary suite with full bathroom, and the other 2 bedrooms share a full hall bathroom. The lower level features the 4th bedroom with walk-in closet and adjoining full spa bathroom. This room can also function as a family room with full wet bar if you just need a little more relaxing space. This level is finished off with a laundry/utility room and garage entry. The location of the home is perfect for commuters and is less than 10 minutes to I-95 and a short trip to Delaware for work and tax free shopping, as well as all points south along the I-95 corridor to Washington, DC. Recreation abounds with a short trip to Elk Neck State Park, approximately 30 minutes away. The park features the Turkey Point Lighthouse which sits on a high bluff overlooking the Chesapeake Bay, Elk, and Northeast Rivers. The park offers campgrounds, rustic cabins, swimming, fishing, crabbing, miles of trails for hikers and bikers, as well as boat and canoe/kayak launches. This home is ready and waiting for you to come home! Schedule your tour today, don't wait! SHOWINGS BEGIN 11/2/25

Motivated Sellers!!! Welcome to 121 Primrose Road, a spacious two-story residence offering 2,034 square feet on a .345-acre lot. This well-built home delivers comfort, functionality, and potential in a peaceful setting just outside downtown Chestertown.Inside, you’ll find three bedrooms and two full baths upstairs plus a convenient half bath on the main level. The main floor features a bright living area, a classic dining space, and a large all-seasons room off the kitchen—perfect for gatherings or relaxing year-round. The full basement offers a blank slate, ready to finish as a recreation room, workshop, or extra storage.A brand-new septic system provides peace of mind, while the attached two-car garage and expansive back deck add everyday convenience. Situated on the Queen Anne’s County side of Chestertown, this property keeps you close to the shops, restaurants, and waterfront charm of downtown while offering the privacy of a quiet neighborhood.

WOW! 2.5 ACRES!! - Enjoy peaceful country living in this charming 3-bedroom, 2-bath rancher set on 2.5 acres backing to open farmland. The home welcomes you with a comfortable living room featuring a cozy gas fireplace and a separate dining space just off the kitchen. The kitchen offers newer appliances and opens to an enclosed sun room—a versatile space perfect for an office, playroom, art studio, or home gym.The primary bedroom includes a remodeled private bath with a walk-in shower, while two additional bedrooms share a conveniently located hall bath. Outside, you’ll find a detached 2-car garage, ideal for vehicles, storage, or stowing your kayaks for quick trips to the nearby Choptank River.The full unfinished basement has inside access from the kitchen, as well as an outside entry. The basement has been completely framed in for some rooms and a large open family room area. The basement provides another 1344 sqft of space.With 2.5 acres of open land, the property offers future potential for a pasture, small crops, a pool, or even a barn. Located just minutes from Greensboro and a short drive to Denton for shopping and dining, this home blends country charm with modern convenience.

Live with ease in this beautifully updated and maintained one floor home in downtown Chestertown. The current owners put a large addition on the house that includes a family room with wood burning stove, sunroom, and primary suite with en suite bathroom and walk in closet. A large laundry room on the main floor and updated kitchen with tons of counter space were other valuable design updates. The basement provides ample partially finished storage space in a completely dry environment due to serious structural improvements, sump pump and french drain system. Bring your hobby down there or your trusty work bench. The roof, HVAC, and hot water heater are all less than 10 years old. The front yard provides a polished experience with tasteful landscaping. The rear yard is quite large for a house in town and includes a raised bed garden and tidy shed. Experience the relaxed lifestyle of Chestertown with the Historic District's shops, Washington College, and the Margo Bailey park just a short walk away.

Move-in ready and freshly updated in 2025! This 3-bedroom, 2-bath home offers approx. 1,600 sq. ft. of stylish living on a .387-acre corner lot with public water and sewer. Every detail has been thoughtfully upgraded—appliances and systems are brand new, complemented by luxury vinyl plank flooring throughout. The spacious layout includes a large mudroom and plenty of modern finishes. Located just minutes from Fairlee Creek’s public landing for easy water access, and a short drive to downtown Chestertown and Rock Hall, this home combines comfort, convenience, and Chesapeake charm. PROPERTY CAN BE PURCHASED FOR AN ADDITIONAL COST WITH LISTING MLS #MDKE2005074, 1.8 ACRES SUBDIVIDED INTO 4 LOTS TO MAKE THIS LOT AN ESTIMATED TOTAL OF 2.19 ACRES!

Welcome to 204 S Church Street — a charming 3BR/3BA home in the heart of Sudlersville!This beautifully maintained and thoughtfully updated home offers comfort, style, and modern conveniences. One of its standout features is the spacious first-floor primary bedroom complete with a private en-suite bathroom, offering ease and accessibility rarely found in homes of this style. This home boasts 3-bedrooms and 3 full bathrooms and features a wrap-around porch perfect for morning coffee or evening relaxation.Inside, you'll find an inviting layout with granite countertops in the kitchen, a cozy fireplace in the living area, and dual-zone HVAC to keep you comfortable year-round. The home is equipped with a tankless water heater, ensuring endless hot water and energy efficiency.Enjoy privacy and room to play in the fully fenced-in yard, ideal for pets, gardening, or entertaining. O head over to nearby Sudlersville Park!This move-in-ready gem offers the perfect combination of small-town living and modern amenities.Don’t miss your chance to make it yours!

Great rancher in Chester Harbor on the Queen Anne's County side of Chestertown. Fresh paint and carpet throughout. Both bathrooms are completely remodeled. The kitchen could use updating, but the space is great and the appliances are in excellent condition. Plenty of room to add a kitchen island and still have space for a table. Nice 2 car detached pole barn style garage. Fenced back yard. This property has a lot to offer!

Looking for a 3 bed farmhouse in Millington with classic charm and modern updates? This warm and friendly 1920 single family home offers 1508 square feet on a 0.17 acre lot with a 2021 roof, vinyl siding, three second floor bedrooms, one full bath, and a half bath off the kitchen. A wrapped front and side porch sets the tone, while a rear wooden deck opens to the yard for easy outdoor living. The heated rear garage includes driveway parking and a setup that allows welder hookup, ideal for hobby work or small trades. Inside, the layout provides a cozy front living space, practical kitchen flow, and natural light throughout. Located in Millington with quick access to Route 301.

Clean, classic mid-century style ranch with REAL wood floors. archways, knotty pine kitchen, a big front porch, large yard, off-street parking and bonus alley access in rear with possible room for a detached garage (buyer to verify) New upgraded electrical service and GFCI outlets, fresh paint, floors refinished and more. Walk to conveniences from this move-in ready charmer in upper Chestertown.

Kent County welcomes you with a move-in ready home that’s full of updates! This 3-bedroom, 2-bath home sits on nearly a half-acre and is just minutes from downtown Chestertown. Enjoy peace of mind with a newer roof (approximately 5 years old), central heat and air, and a tankless water heater. The home features updated bathrooms, fresh interior paint, and a large laundry room with abundant shelving and space for storage. Outside, you’ll find a spacious yard, storage shed, and access to a wonderful community park with a pavilion and basketball courts. A great combination of comfort, convenience, and value in a desirable location! Kent County has 21 marinas, all within minutes of this location. Live, work and play here in Kent County!

Spacious and versatile, this 4-bedroom, 2.5-bath home offers endless possibilities! Perfectly situated on a large corner lot and zoned Village, the property features a first-floor bedroom with a private entrance—ideal for a home office, daycare, or other business use.When purchased in 2020 it received a new roof, septic, and well, and more recently the seller has updated the 2nd-floor HVAC system for added efficiency and comfort. Inside, you’ll love the large eat-in kitchen, brick sunroom filled with natural light, and dual-zone heating & air.Located just minutes from downtown Chestertown and some of the area’s most popular marinas, this property combines small-town convenience with Chesapeake lifestyle charm & business potential!

Enjoy coastal living this fall and beyond with this meticulously maintained, fully furnished, turn-key 1-bedroom, 1-bath condo in Ocean City, MD. Perfectly situated on the first floor, you’ll appreciate the ease of access—no stairs to climb when bringing in luggage or supplies. Inside, the open-concept kitchen and living area provide a bright, welcoming space to relax or entertain. Step outside to your spacious balcony, complete with comfortable furniture, hurricane shutters, and a convenient storage shed for beach gear and toys. Recent upgrades include a new washer/dryer (2023), refrigerator (2019), and a Google Nest thermostat that allows you to control the climate remotely. After a day at the beach, rinse off in the community’s outdoor shower before heading inside. Parking is included for added convenience.Just two short blocks from the ocean and within walking distance to the historic Ocean City Boardwalk, Jolly Roger Amusement & Splash Mountain Water Park, plus countless restaurants and shops—this location offers the best of everything. The Jamaica Daybreak Condo Association recently completed extensive exterior renovations (May 2025), with all assessment fees already paid in full by the seller—giving buyers peace of mind. With some of the lowest condo fees in the area at just $325/month, you’ll also enjoy discounted cable TV and internet. Lovingly owned for 20 years and never rented, this condo is move-in ready and waiting for its next chapter.

A home finished your way with what could be over 3,078 square feet of living space! Complete your new Victorian style home with the finishes & colors you enjoy! Located within a .3 mile walk to Betterton Beach and the Town Dock! Public showers, rest rooms and transient boat slips are all at your disposal! The interior of the home is a blank slate and has been protected from the elements. The home features a full concrete basement, 4X6 construction, a large kitchen space with access to the garage and the wrap around porch, formal dining, living room with an octagon window setting allowing natural light to fill the room and full bath on the 1st floor. Moving up the stairs to the 2nd floor are 3 bedrooms 2 full baths, laundry and the possibility for a large 4th bedroom or playroom/game room! Quality Anderson windows throughout and steel entry doors. The large two car garage has ample space for your bikes, jet ski and all your water toys! A builder/contractor is awaiting your call, with enough notice I can have a Builder/contractor walk through with you as you discuss your needs, likes and wants along with your budget! This is not a rehab, the home was built and never finished.

Live just down the road from Fairlee Creek! Public access is less than a mile away allowing the Chesapeake Bay at your fingertips! Great Oak Marina sits at the inlet of Fairlee Creek and The Bay offering a full service resturant, marina and Tiki Beach Bar. A summer full of entertainment, boating, fishing, crabbing, jet skiing, tubing, skiing or anything else your heart deserves! Public water and sewer has been confirmed as available to purchase for each lot.Lot #2 - .259 acresLot #3 - .266 acresLot #4 - .431 acresLot #5 - .452 acres

Great Investment Opportunity – Fixer-Upper on 1 Acre LotAttention DIYers, investors, and renovators! This small home, located on a beautiful 1-acre lot, is a diamond in the rough, offering endless potential for the right buyer. Nestled in the quiet, rural setting of Quaker Neck just 1.5 miles from downtown Chestertown, this property is the perfect canvas for a major rehab project.The home, which is in need of significant repairs and updates, is being sold as-is, providing a great opportunity to bring your vision to life. Whether you're looking to restore it to its original charm or transform it into something entirely new, this property offers a solid foundation for your renovation ideas.Property Highlights:* 1-acre lot with plenty of space for expansion, gardening, or outdoor activities* Small house with potential to become a cozy retreat or a profitable rental* Quiet, rural location for privacy and peace of mind* Easy access to Chestertown for shopping and Quaker Neck Landing for water fun!Please note: This home needs extensive repairs and will not qualify for traditional financing, so it's ideal for cash buyers or those with renovation experience. Buyer to perform due diligence. Sellers are willing to provide architectural drawings & site plans for their planned renovation.Don’t miss this opportunity to turn a fixer-upper into your dream home or next big project. Schedule a showing today and imagine the possibilities!

Wonderful lot in Betterton, only 2 blocks from the beach, and your chance to make wonderful memories in this community known as the Jewel of the Chesapeake. Betterton sits right on the upper Chesapeake Bay at the mouth of the Sassafras River, an extremely popular boating area. The beach is beautiful with calm waters and amenities for a perfect day at the beach. This community is certainly a treasure and one of the areas best kept secrets! Don't miss out on your chance to build your dream home in one of the best little spots in Maryland! Water/Sewer Allocation is available through the town.

(Lot 2 - .685 acres & Lot 3 - .689 acres) Conveniently located slightly off 291, in a private area on a dead-end road, this property is close to Chestertown and minutes away from route 301. Lots sit high off the road level and adorned with young saplings. Soil evaluation from 2011 approved for 3 beds and a 2,000 sq ft home, located just outside the critical area. Lots being sold together!

Come build your dream home. Located right off E Sharp Street on Chesapeake Villa is your .46 acre lot. Location is perfect to everything Rock Hall has to offer, from shops to restaurants to the water. Come check it out today.Lot has water/sewer hookup available, contact town of rock hall to confirm fees.

Wooded lot located in the waterfront community of Chesapeake Landing. There is a voluntary HOA that you can join for a fee to join to gain access to the boat ramp and Marina. Lot backs up to farm land.