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

Two fantastic building parcels just off the Chester River. 1.36 acres total on a cul-de-sac at the end of a quiet road. Perc approved and ready for you to design your dream home on the Eastern Shore. Crabbing, fishing, swimming, birdwatching, you name it! Bring your house plans or just camp out and build a fire. Level building area sits on a small bluff well above the water: no flood zone! Public boat landing only a few blocks away. Easy access to Route 301. 90 minutes to Philadelphia, South Jersey, and Washington D.C. 30 minutes to Middletown, Delaware and tax-free shopping. Less than 15 minutes 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 and an award-winning weekly Farmer's Market. Property is marked by sign. Perc approval and survey on file. Parcels sold together, not separate. Drive-bys permitted. Do not enter property without an appointment.

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.

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!!

***Photos reflect the progress as of 3 months ago. The property is now nearly completed and is simply awaiting a finishing coat of paint and a layer of sod on the newly fenced in rear yard. A superb level of craftsmanship and scope of work not to be missed.***Pricing reflects the property fully finished and professionally cleaned. This is a rare chance to own a completely restored legacy home on Chestertown Historic District’s most prominent corner. Water views are appreciated from two sides. Great balance of modern amenities and layout matched with historic design elements and style. The builders who took on this passion project are some of the most renowned in Kent County. 30 day estimated timeframe to complete upon contract acceptance. The detached garage is a huge plus with highly sought after off street parking.

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!

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 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.

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.

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.

Enjoy the waterfront lifestyle with this one floor gem perched up on the banks of the Choptank River just 10 minutes from historic Denton. Relaxation and a connection with nature are easily achieved inside and outside of the home. Outdoor living areas are abundant with a private screened-in gazebo to sit back and enjoy the wildlife, winter deck to catch some rays, and a back patio with Choptank views and no houses on the opposite shoreline. Upon walking into the home, this same goal is achieved with large windows along the water side providing sweeping views. The river room has glass all of the way around flooding the space with light and perfect for reflection or entertaining. Hardwood floors bring serious charm and warmth to the home. The primary bedroom is spacious and includes an ensuite bathroom while the other two bedrooms provide river views. An oversized 2 car garage allows extra space to mess around on your workbench and store those beloved kayaks. The large and cleared yard has a split rail fence and trees that along with the meandering paved driveway provide a sense of privacy. The community itself is very quiet and has the Jim and Mary B. Lynch Preserve adjacent which provides roughly 2 miles of walking trails and is currently managed by the Eastern Shore Land Conservancy. Make this your own tranquil Eastern Shore retreat.

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.

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!

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!

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.

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.

Don’t let the outside fool you—this beautifully renovated 3-bedroom, 1.5-bathroom home offers three levels of living space, with over 2,200 sq. ft. above ground and an additional 550 sq. ft. below ground! Every inch of this home has been thoughtfully updated to blend modern comfort with timeless charm.Step inside to discover a stunning custom kitchen, a true chef’s dream featuring a gas stove, upgraded quartz countertops, solid wood cabinetry, and stylish open shelving—perfect for both cooking and entertaining. The spacious living areas boast brand-new LVP flooring, fresh finishes, and an inviting atmosphere throughout.Upstairs, the primary bedroom is a private retreat, complete with a mini-split AC/heat unit, a large dressing room, and a convenient half bath.Head downstairs to a versatile lower level, where an open-concept space offers endless possibilities—whether you need a media room, game area, crafting space, or home gym. The large laundry area and utility room provide added functionality.Step outside to your own backyard oasis, enclosed by a beautiful privacy fence. Enjoy the spacious patio, detached garage/barn, and storage shed—ideal for hobbies, storage, or workshop space.This home is completely move-in ready and packed with upgrades—all it needs is you! Don’t miss your chance to see this hidden gem—schedule your private showing today!

This Mid Century Modern is located in Mile Tree Village, one of Chestertown's most coveted neighborhoods. One floor living makes things a breeze with this open and easy floor plan. Serious structural updates have been performed on the home, the crawl space has been encapsulated, and the kitchen and bathrooms have been remodeled. The home was also recently had the entire exterior painted and much of the interior as well. The primary suite includes an en suite bathroom, make up parlor, and walk in closet. Outdoor living is a plus here with a partially shaded, fully fenced rear yard which includes a deck and a front private courtyard perfect for dinner parties. The detached 2 car garage allows for storing all of the toys that come along with the Eastern Shore lifestyle. This is the perfect balance with walkability, a spacious yard and the tranquility of living on a quiet cul de sac.

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.

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!

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.

Adorable rancher in a PRIME location in Rock Hall. Just steps to the marinas, restaurants, and shops. The house has been completely remodeled. 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. Beautiful, low-maintenance perennial gardens with pretty paths weaving through the yard. Detached garage and shed. Less than 1/2 mile to the public beach. 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!

Interior photos coming but for now refer to the photos on the previous listing

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.

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!

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.

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.

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!

Welcome to Shorewood Estates, a water privileged community on Swantown Creek just off the Sassafras River. This well maintained home offers an updated kitchen with granite counter tops, a master bedroom and bath with two other bedrooms and bath on the main level and a large family room on the lower level along with a sewing room or home office. There is a detached screened porch perfect for a crab feast or just enjoying the landscaped yard. In addition there are raised beds with drip irrigation for your vegetable or herb garden. Two community areas provide access to the water - one has a little sandy beach with picnic tables where you can launch kayaks and canoes and the other with a dock and slips available through a yearly lottery. The Shorewood Estates Civic Association is voluntary. This property could be a second home escape or primary residence with its easy access to Rt. 301. Come and enjoy all The Land of Pleasant Living has to offer!

Welcome to 12776 Still Pond Road: an endearing early 20th Century Victorian in the quiet town of Still Pond. This could be the perfect Eastern Shore retreat or full time residence. Historic Charm abounds with pocket doors, bay windows, 9 foot ceilings, hardwood floors, bullseye corner moldings, mahogany front porch, oak mantels, custom built-ins, and so much more. Enjoy rolling farmland views and picturesque sunsets from the front porch swinging bench. The sun-filled formal parlor flows seamlessly through the large pocket door into the dining room and kitchen. Follow the solid-wood staircase and railing upstairs to find 3 generously sized bedrooms and a 4th bedroom or office space. Massive 3rd floor could be finished for a 4th bedroom or den / game room. Recent upgrades include: architectural shingle roof, 6 mini-split systems for central heating and air, water conditioner, water heater, fireplace mantel with propane insert, and a brand new Fuji septic system. Almost 3/4 of an acre allows plenty of space for the dogs and kids to play. Open farmland surrounds for great views from any direction. Less than 90 minutes to Philadelphia and Washington D.C. 30 minutes to Middletown, Delaware and tax-free shopping. Close to Turners Creek State Park, Betterton Beach and the restaurants/marinas in Galena on the Sassafras River. 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 with full gym, racquet sports, lap pool, sauna, etc. Enjoy country living on the Eastern Shore.

Price improvement! Cute as a button in the historic district on South Kent St. This 1-bedroom, 1.5 bath home is in the center of town, within walking distance to the farmers market and all the shops and restaurants. Just 4 blocks from Chestertown's waterfront promenade. Upstairs is a large, sun-filled room with a spacious closet that serves as an office. It could also be a den or sitting room. Then enter the large bedroom and bathroom with a view of the garden below. The house has many possibilities for expansion. The mature garden is a delight with trees and perennials throughout, surrounded with summer flowers. Perfect for one or two people as a full-time residence or weekend getaway.

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!

Updated in 2024 by a loving family member & their licensed professional! This charming 3-bedroom, 2-bath home offers a perfect blend of modern updates and country serenity. The main level features a convenient first-floor bedroom and full bath, ideal for aging in place. Enjoy stylish & durable vinyl plank flooring throughout and soaring cathedral ceilings upstairs that create an airy, open feel. Situated on a spacious corner lot on almost a half of an acre & a newly installed well. Whether it’s a morning coffee or an evening cocktail for watching sunsets, enjoy the cozy front porch where you can relax and take in the sweeping views of the surrounding farmland. A peaceful retreat with thoughtful upgrades—move-in ready and waiting for you! - Buyer got cold feet, walked and never scheduled inspections , terminated in default and forfeited their EMD -

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!

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.

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, 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.

Welcome home to this charming 3-bedroom, 1-bath rancher offering single-level living with thoughtful updates inside and out. The former garage has been converted into a spacious primary bedroom, adding approximately 300 sq. ft. of living space while still retaining some storage at the front.The exterior has been fully remodeled in recent years, featuring new siding, roof, windows, and a cozy rear porch. Inside, the split floor plan places the primary bedroom on one side of the home, with two additional bedrooms on the opposite side for privacy. The spacious living room flows into the remodeled kitchen, complete with new flooring, cabinetry, countertops, and appliances. Just off the kitchen is a versatile flex space—perfect as a dining area, home office, playroom, or creative studio. The bathroom has also been stylishly updated. Step outside to enjoy the newly added patio, ideal for outdoor dining, grilling, and entertaining. The backyard includes a storage shed and plenty of open space for a garden, lawn games, or even a small pool or horseshoe pit. Located just minutes from Denton or Greensboro, this lovely home combines modern updates with a convenient location. Don’t miss the chance to own this perfect little piece of the Eastern Shore! ONE YEAR HOME WARRANTY INCLUDED

Fantastic opportunity to own over 5 acres of buildable, level farmland with two perc approval sites. AG Zoning allows a wide range of residential, outdoor recreational and commercial uses. Property recently surveyed with a custom site plan and ready for your building plans. Property backs to 60+ acre farm in a perpetual forest conservation easement. Right of ways from 213 and neighbors driveway allow two different access points to property. Entire property is tillable. No deeded covenants or restrictions. Easy access to Route 213, Chestertown, Church Hill and Centreville. AG Tax paid by current owner. Buyer to perform own due diligence. Do not enter property without an appointment.

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!

Great chance to purchase a corner lot just across the river from Chestertown's Historic District. Sit and listen to the birds by the pond on this peaceful retreat just minutes from the town's shops, galleries, and waterfront. There aren't many more opportunities like this. Please see the documents for the perc approval and site plan.

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.