Chestertown MD Real Estate & Homes for Sale

This beautiful custom home on an acre of land has 4 Beds and 2.5 baths. There is an eat-in-Kitchen with granite countertops that is completed by the Maple Wood Island, Gas cooking, and stainless steel appliances, soft close cabinets and 2 pantry's. This home has a Large living and Dining room too! The 'Florida Sunroom' allows could be an office or a place to read a book in the sunshine and the double doors lead out to your fenced in yard. Acacia hardwood floors throughout! This home boasts a new water treatment system (owned) and gutter guard system so you don't have to worry about all the trees that make this home your private oasis in the woods. Upstairs the primary bedroom has a beautiful ensuite bath with separate jetted tub, shower and a double vanity. It also has walk in closest with a window as well as an additional large closet. There is a dedicated laundry room upstairs, ample closet space and 3 other bedrooms that share an updated bathroom. Don't forget the garage and storage room with 2 decks outside! Schedule your showing today!

Cute rancher in Chesapeake Landing. Nice front porch. Large living room with a woodstove with brick hearth and mantle. Laminate flooring throughout most of the house. 3 bedrooms and 2 full baths. Guest bathroom is a great size and also contains the washer dryer. Stainless appliances. Kitchen Island. Nice sized lot with multiple sheds. A great property at a great price!!!

Welcome to your new home in the Village at Chestertown! Built in 2023, this home offers modern living new construction with many upgrades. Featuring three spacious bedrooms and two and a half bathrooms, this home is move-in ready and waiting for you. Step inside to discover a beautifully upgraded kitchen with stunning quartz countertops, tile backsplash, and stainless steel appliances. The open-concept living area is perfect for entertaining, centered around a cozy electric fireplace with a charming shiplap accent wall, creating a warm and inviting atmosphere. Outside, you'll find a fenced rear yard, ideal for privacy and outdoor activities. Whether you're hosting a summer barbecue or enjoying a quiet evening under the stars, this space is perfect for all your outdoor needs. Additionally, the detached 12x24 garage provides ample storage and parking space. Every detail in this home has been thoughtfully designed for comfort and style, making it the perfect place to start your next chapter. Don't miss the opportunity to make this home your own. Schedule a viewing today and experience the best of modern living in the sold out Village at Chestertown!

Welcome to 101 Landing Lane, an exquisite residence offering exceptional living in the prestigious Chester River Landing Community. Boasting an expansive 3,300 square feet of meticulously designed living space, this home features luxurious amenities and elegant finishes across three levels, ensuring comfort and style at every turn.Step inside to discover the warmth of hardwood floors that flow seamlessly throughout the home. The main level features a spacious guest bedroom and a full bath, perfect for accommodating visitors with style and ease. A well-appointed study on this level offers a quiet retreat for work or relaxation, ensuring a versatile and functional living space. The lower-level deck is perfect for relaxing with a good book, overlooking the scenic community pond, and the attached one-car garage provides parking and storage space. The second level's open floor plan integrates the kitchen, living room, and dining room, creating an inviting space ideal for modern living and entertaining, with hardwood floors throughout. The gourmet kitchen is a chef's dream, showcasing rich wood cabinets, stone countertops, and stainless steel appliances. The living and dining areas extend effortlessly to an upper-level balcony, perfect for al fresco dining and providing serene views of the community pond. The primary bedroom on this level offers a luxurious sanctuary with a large walk-in closet and beautifully finished bathroom The third level is designed for leisure and entertainment. Here, you'll find an additional bedroom and a versatile game room, perfect for family fun or casual get-togethers. The game room can be adapted to suit your lifestyle needs, whether as a media room, playroom, or hobby space.Residents enjoy easy water access and exclusive use of the community's private dock and swimming pool. The swimming pool offers a refreshing escape during the warmer months, perfect for relaxation and recreation. Experience the epitome of elegant living in a vibrant and friendly community in this move-in ready home. Don't miss the opportunity to make 101 Landing Lane yours. Schedule a private tour today and discover all the exceptional features this property has to offer.

Looking for something truly special? Don't miss this unique offering, located in the vibrant heart of Chestertown's Historic and Arts & Entertainment Districts! Boasting a legacy of over half a century under the stewardship of one devoted family, this multi-family property presents a rare opportunity for visionary investors and passionate renovators alike. Situated on a generous lot, steeped in the rich history of Chestertown and prominently featured on historic maps as the Laurence Lots, this property offers a canvas brimming with potential. Whether you envision revitalizing it into a majestic single-family residence or retaining its current configuration with a townhouse on one side and two apartments on the other, the possibilities are boundless. While the property stands as a testament to enduring charm and character, it's essential to note that significant settling has occurred over the years. As such, unlocking its full potential will necessitate considerable renovation efforts. This property is a bona fide fixer-upper and is exclusively offered in its current "as is" condition, awaiting the transformative touch of its next custodian. With its prime location , this property represents not only an investment opportunity but a chance to become part of Chestertown's storied legacy. Seize the chance to breathe new life into this home and craft a future brimming with possibility. Embrace the challenge, unleash your creativity, and make your mark on Chestertown's captivating tapestry of history and culture. Schedule your viewing today and prepare to embark on an unforgettable journey of restoration and renewal!

Well maintained Cape Cod in the sought after Coventry Farms subdivision in Chestertown - 1st Floor Master Bedroom includes a spacious walk in closet and a large Full Bath with Walk in Shower - 4 bedrooms, 2.5 baths, a spacious living room, and a large kitchen makes this home irresistible - Be sure to step outside from the dining room through the sliding glass door into the large screened-in deck - Perfect for outdoor entertaining or sitting comfortably and enjoying the secluded backyard greenery.

Construction will be done in 3 weeks, but come see it TODAY! Just over 1500 sq' - Three (3) bedrooms and Two and a half (2.5) baths. It boasts water views of the Chester River and an open-concept layout. The kitchen has stainless steel appliances, and the main-level master suite has a walk-in closet and ensuite. Upstairs, you'll find two more generously sized bedrooms and an additional full bathroom. High speed internet is available. The home is located at the end of a quiet, private street. Queen Anne's County Impact Fees have been paid by the Seller.

Welcome to a captivating opportunity to reside in the idyllic neighborhood of The Grove in picturesque Queen Anne's County. Prepare to be enchanted by this charming abode, where every detail exudes warmth and comfort.Step inside and be greeted by the timeless elegance of hardwood floors and plush carpeting, inviting you to kick off your shoes and make yourself at home. The heart of the main floor boasts a cozy gas fireplace, creating a cozy ambiance perfect for intimate gatherings or quiet evenings curled up with a good book.With four bedrooms and 2.5 baths, there's ample space for your family to spread out and relax. The open floor plan seamlessly connects the living spaces, allowing for effortless flow and easy entertaining. The kitchen, a culinary haven, beckons with its modern amenities and ample counter space, inspiring culinary creativity and culinary delights.Recent updates abound in this haven of comfort and style, including new skylights that bathe the interiors in natural light, and a spacious deck where you can savor morning coffee or evening cocktails while overlooking your fenced backyard and the serene vistas of rolling farmlands.Venture downstairs to discover a sprawling recreation room, offering endless possibilities for entertainment and relaxation. Whether you envision a home theater, a game room, or a fitness area, this versatile space is ready to fulfill your every need. A separate office provides a quiet retreat for work or study, while an additional bedroom offers flexibility for guests or extended family.Storage woes are a thing of the past, with plenty of space to stow away your belongings or unleash your creativity to reimagine the possibilities of each room.Embrace the quintessential charm of country living while still enjoying the convenience of modern amenities. The Grove offers a tranquil escape from the hustle and bustle of city life, with its tree-lined streets and sense of community.Don't miss your chance to make this enchanting retreat your own. Schedule a viewing today and embark on a journey to a life of comfort, convenience, and timeless elegance in The Grove.

A stunning renovation in the historic district! This stately brick colonial overlooks the meticulous campus green at Washington College; a view that invites a walk to downtown Chestertown, and a location that gives you a front row seat to college activities and events. It is also one short block to the University of Maryland Shore Medical Center. A desirable rear alley, provides access to the home's private off-street parking space and the carriage-styled garage, which can accommodate a SUV. Located on the first floor off the center hall,is the living room, dining room, kitchen, den/office, half bath, all- season sun room, and inside stairs to the full basement, The new custom kitchen showcases an individually handcrafted brick floor and an imported Spanish tiled backsplash. Wrap around natural lighting, open shelving, oversized island and walk in-pantry make this kitchen one of a kind, and completes the first floor. The second floor begins with the original grand stairway and a cozy sitting area in the window nook at the end of the catwalk. The primary bedroom comes with a five piece luxury en-suite bath, while two additional bedrooms share a full bathroom off the landing. The dedicated laundry room, also on the second floor, has storage cabinets, room for ironing and folding and a cleaning supply niche. The third floor garret-studio apartment completes the living areas inside this home. This spacious studio has a full bathroom, dedicated cooking & eating area and independent climate control. A comfortable sitting area and separate sleeping space, and separate desk space round out this studio. There is also a full basement of approximately 1100 square ft with both interior access and a highly coveted exterior access. 7.5 foot high basement ceilings, provide an excellent opportunity to design an additional apartment, fitness studio, family room, wood shop etc. Exterior and mechanical upgrades include: a new roof, gutters & downspouts, a new front landing with oversized walkways and raised brick landscape beds. Significant wiring upgrades include a new electrical service and wiring for new electrical components. Plumbing upgrades include a new main shut off valve and a new water line between the house and street. Replacement of most of the interior plumbing was done to accommodate updated fixtures. The one-car, carriage styled garage has been placed for optimum versatility. It makes a charming extension of the outdoor entertaining space to effortlessly plan for changeable Chesapeake-country weather. Simply move the car, open the barn doors, turn on the the oversized crystal chandelier and the tone is set for gatherings protected from the elements! With the double barn doors opened, the terraced courtyard can be incorporated into any event. This property is fully fenced & gated providing privacy for outdoor activities and security for family pets. This brick center-hall colonial has been extensively renovated and is turn-key! Square footage is estimated: buyer to verify. A complete upgrade record is available upon request. Talk to your agent about possible owner financing on this home.

Welcome home to this stunning new construction in Chestertown's prestigious waterfront community, Chester River Landing. This exquisite three-bedroom, two-and-a-half-bath home offers luxurious living and breathtaking views of the Chester River. Nestled in a serene setting, this property blends modern design with coastal charm. The spacious, open floorplan layout provides ample room for relaxation and entertaining. With high-end finishes including granite countertops, luxury vinyl and tile flooring, Hardie plank siding, stainless steel appliances, etc. and attention to detail, this home promises a lifestyle of comfort and sophistication. Immerse yourself in the beauty of the waterfront community, enjoying the bbq/picnic area, shell walking paths, community pool and the deep-water community dock. The Chester River Yacht and County Club is a short way up the road to play a round of golf, fine dining and social events or head into historic downtown Chestertown just minutes away for shopping, restaurants, plays, farmer's markets and more!

Welcome home to this stunning new construction in Chestertown's prestigious waterfront community, Chester River Landing. This exquisite three-bedroom, two-and-a-half-bath home offers luxurious living and breathtaking views of the Chester River. Nestled in a serene setting, this property blends modern design with coastal charm. The spacious, open floorplan layout provides ample room for relaxation and entertaining. With high-end finishes including granite countertops, luxury vinyl and tile flooring, Hardie plank siding, stainless steel appliances, etc. and attention to detail, this home promises a lifestyle of comfort and sophistication. Immerse yourself in the beauty of the waterfront community, enjoying the bbq/picnic area, shell walking paths, community pool and the deep-water community dock. The Chester River Yacht and County Club is a short way up the road to play a round of golf, fine dining and social events or head into historic downtown Chestertown just minutes away for shopping, restaurants, plays, farmer's markets and more!

Welcome home to this stunning new construction in Chestertown's prestigious waterfront community, Chester River Landing. This exquisite three-bedroom, two-and-a-half-bath home offers luxurious living and breathtaking views of the Chester River. Nestled in a serene setting, this property blends modern design with coastal charm. The spacious, open floorplan layout provides ample room for relaxation and entertaining. With high-end finishes including granite countertops, luxury vinyl and tile flooring, Hardie plank siding, stainless steel appliances, etc. and attention to detail, this home promises a lifestyle of comfort and sophistication. Immerse yourself in the beauty of the waterfront community, enjoying the bbq/picnic area, shell walking paths, community pool and the deep-water community dock. The Chester River Yacht and County Club is a short way up the road to play a round of golf, fine dining and social events or head into historic downtown Chestertown just minutes away for shopping, restaurants, plays, farmer's markets and more!

Welcome home to this stunning new construction in Chestertown's prestigious waterfront community, Chester River Landing. This exquisite three-bedroom, two-and-a-half-bath home offers luxurious living and breathtaking views of the Chester River. Nestled in a serene setting, this property blends modern design with coastal charm. The spacious, open floorplan layout provides ample room for relaxation and entertaining. With high-end finishes including granite countertops, luxury vinyl and tile flooring, Hardie plank siding, stainless steel appliances, etc. and attention to detail, this home promises a lifestyle of comfort and sophistication. Immerse yourself in the beauty of the waterfront community, enjoying the bbq/picnic area, shell walking paths, community pool and the deep-water community dock. The Chester River Yacht and County Club is a short way up the road to play a round of golf, fine dining and social events or head into historic downtown Chestertown just minutes away for shopping, restaurants, plays, farmer's markets and more!

Looking for something truly special? Don't miss this unique offering, located in the vibrant heart of Chestertown's Historic and Arts & Entertainment Districts! Boasting a legacy of over half a century under the stewardship of one devoted family, this multi-family property presents a rare opportunity for visionary investors and passionate renovators alike.Situated on a generous lot, steeped in the rich history of Chestertown and prominently featured on historic maps as the Laurence Lots, this property offers a canvas brimming with potential. Whether you envision revitalizing it into a majestic single-family residence or retaining its current configuration with a townhouse on one side and two apartments on the other, the possibilities are boundless.While the property stands as a testament to enduring charm and character, it's essential to note that significant settling has occurred over the years. As such, unlocking its full potential will necessitate considerable renovation efforts. This property is a bona fide fixer-upper and is exclusively offered in its current "as is" condition, awaiting the transformative touch of its next custodian.With its prime location , this property represents not only an investment opportunity but a chance to become part of Chestertown's storied legacy. Seize the chance to breathe new life into this home and craft a future brimming with possibility. Embrace the challenge, unleash your creativity, and make your mark on Chestertown's captivating tapestry of history and culture. Schedule your viewing today and prepare to embark on an unforgettable journey of restoration and renewal!

Wonderful renovation, modern, efficient, and move in ready! Home features vaulted ceilings with open flexible floorplan and 2 brand new luxury bathrooms. Energy efficient instant hot water heater. Large side deck, plenty of parking, small storage shed, and updated BAT system septic. Spacious yard for a garden and family events. Can't pass up this AFFORDABLE price point for like new construction, but not a townhouse!

A stately 1800's waterfront Victorian home, rich in history enters a new chapter in life with 6 new condominium units. Make sure to bring all you water toys or a lounge chair to relax on the banks of Chester River. All the units have been renovated with with upgraded bathrooms and brand new kitchens. Enjoy all the amenities of living waterfront--Community dock, kayak storage, patio, and your own ground level storage. This is a unique setting offering waterfront living in downtown historic Chestertown and includes off street parking. Walk to downtown restaurants and shops. Beautiful southeast views of the Chester River with spectacular sunrises and plenty of year-round sunshine. Take in the all of the nearly year-round waterfront activities from your own back yard, including Chestertown Tea Party, 4th of July fireworks and Sultana down rigging weekend. Located on Maryland's scenic eastern shore less than 85 miles from Washington DC to the south or Philadelphia to the north, this home is the perfect meeting spot for those living in the Mid-Atlantic region. This unit offers a 2 Bed 1 bath has a brand new kitchen and upgraded bathroom along with broad southeast river views.

A stately 1800's waterfront Victorian home, rich in history enters a new chapter in life with 6 new condominium units. Make sure to bring all you water toys or a lounge chair to relax on the banks of Chester River. All the units have been renovated with with upgraded bathrooms and brand new kitchens. Enjoy all the amenities of living waterfront--Community dock, kayak storage, patio, and your own ground level storage. This is a unique setting offering waterfront living in downtown historic Chestertown and includes off street parking. Walk to downtown restaurants and shops. Beautiful southeast views of the Chester River with spectacular sunrises and plenty of year-round sunshine. Take in the all of the nearly year-round waterfront activities from your own back yard, including Chestertown Tea Party, 4th of July fireworks and Sultana down rigging weekend. Located on Maryland's scenic eastern shore less than 85 miles from Washington DC to the south or Philadelphia to the north, this home is the perfect meeting spot for those living in the Mid-Atlantic region. This unit offers a 1 Bed 1 bath has a brand new kitchen, with island, and upgraded bathroom along with up and down river views.

A stately 1800's waterfront Victorian home, rich in history enters a new chapter in life with 6 new condominium units. Make sure to bring all you water toys or a lounge chair to relax on the banks of Chester River. All the units have been renovated with with upgraded bathrooms and brand new kitchens. Enjoy all the amenities of living waterfront--Community dock, kayak storage, patio, and your own ground level storage. This is a unique setting offering waterfront living in downtown historic Chestertown and includes off street parking. Walk to downtown restaurants and shops. Beautiful southeast views of the Chester River with spectacular sunrises and plenty of year-round sunshine. Take in the all of the nearly year-round waterfront activities from your own back yard, including Chestertown Tea Party, 4th of July fireworks and Sultana down rigging weekend. Located on Maryland's scenic eastern shore less than 85 miles from Washington DC to the south or Philadelphia to the north, this home is the perfect meeting spot for those living in the Mid-Atlantic region. This unit offers a 2 Bed 1 bath has a brand new kitchen, with island and upgraded bathroom along with up and down river views.

A stately 1800's waterfront Victorian home, rich in history enters a new chapter in life with 6 new condominium units. Make sure to bring all you water toys or a lounge chair to relax on the banks of Chester River. All the units have been renovated with with upgraded bathrooms and brand new kitchens. Enjoy all the amenities of living waterfront--Community dock, kayak storage, patio, and your own ground level storage.This is a unique setting offering waterfront living in downtown historic Chestertown and includes off street parking. Walk to downtown restaurants and shops. Beautiful southeast views of the Chester River with spectacular sunrises and plenty of year-round sunshine. Take in the all of the nearly year-round waterfront activities from your own back yard, including Chestertown Tea Party, 4th of July fireworks and Sultana down rigging weekend.Located on Maryland's scenic eastern shore less than 85 miles from Washington DC to the south or Philadelphia to the north, this home is the perfect meeting spot for those living in the Mid-Atlantic region.This unit offers a 1 Bed 1 bath has a brand new kitchen, with island, and upgraded bathroom along with up and down river views.

Beautifully renovated waterfront on the Chester River, located between historic downtown Chestertown and the Chester River Yacht and Country Club. Renovations include including new kitchen and bathrooms. This property boasts a deep water dock with lift for your boating, swimming and fishing pleasures. Come and enjoy all the Chestertown has to offer with just a short walk to down town shops, restaurants and parks..

This BRAND NEW 3-bedroom, 2.5-bathroom Cape Cod home is move-in ready! It boasts water views of the Chester River and an open-concept layout. The kitchen has stainless steel appliances, and the main-level master suite has a walk-in closet and ensuite. Upstairs, you'll find two more generously sized bedrooms and an additional full bathroom. High speed internet is available. The home is located at the end of a quiet, private street.Queen Anne's County Impact Fees have been paid by the Seller.

Every so often a property like 240 Round Top Landing Road, Chestertown hits the market that checks all the boxes. This Chester River waterfront estate is situated on 10 acres , offering deep water, pier, 25' x 50 ' in-ground pool, screened porch , 3 bedroom/3.5 bath main house and a carriage house. The architectural design and the superb craftsmanship are evident as soon as you enter the driveway. Beautiful trees(Peach,Pear, Pines, Poplars, Sycamores, Magnolias' Crepe Myrtles) enhance the park-like setting. Notable features are geo-thermal heat; gas and wood burning fireplaces, chef's kitchen; first floor spacious primary bedroom suite , and open living areas. As far as the exterior, the stucco siding is either over brick or block so no stucco is over frame. Some poplar siding on main house and cedar siding on carriage house.

Step into a world of timeless elegance and tranquility with this meticulously maintained retreat. As you turn into the Fairgale Subdivision, it feels as though you are entering an estate, with majestic trees lining both sides of the paved road, creating a sense of grandeur and privacy. Nestled on the shores of an oversized pond, this exquisite home offers not only stunning views but also exclusive access to a community dock and dedicated boat slip with a lift onto Fairlee Creek. Originally built in 2000 and impeccably maintained and updated, this home welcomes you with a beautifully designed foyer that sets the bar for living beautifully. The living room, open to a gracious dining area, exudes warmth and hospitality, making it the perfect setting for gatherings with loved ones. French doors beckon you to the covered patio, where you can bask in the serene ambiance and enjoy the sights and sounds of nature. Below, the guinite pool invites you to relax and unwind, surrounded by ample space for poolside lounging and entertaining. The main level boasts four bedrooms, including a luxurious owner's suite complete with a cozy gas fireplace and direct access to the pool area. The master bath is a sanctuary in itself, featuring separate vanities, a spacious walk-in shower, a soothing soaking tub, and generous storage space. The second bathroom, versatile in its design, offers built-in bookshelves and two closets, making it ideal for use as an office or guest suite. A convenient half bath, with access to the pool, adds to the home's functionality and convenience. The recently updated kitchen is a Cook's delight, equipped with an island, ample storage, and all the necessary appliances. Adjacent to the kitchen, the family room beckons with built-ins, a fireplace, and abundant natural light, creating a cozy yet inviting atmosphere. The Florida Room, bathed in sunlight, offers a perfect spot for plants and relaxation, with seamless access to the pool area. Two additional bedrooms, one with an attached sitting room, and a full bath complete the main level, ensuring comfort and convenience for all. Downstairs, a newly added bedroom and bathroom, along with a spacious great room, provide endless possibilities for entertainment and recreation. The expansive storage room offers potential for additional living space or customization to suit your needs. Upstairs, the attic boasts a large cedar room for storage, with even more space available if needed. The quality of construction is evident throughout, ensuring durability and longevity for years to come. Don't miss this opportunity to experience the beauty and serenity of waterfront living at its finest. Schedule a viewing today and make this exquisite property your own slice of paradise in this great neighborhood.

Well maintained 2 bedroom 1 bath Colonial on .69 acres with winter water views of Fishing Creek! Features Include: Screened Porch * 1-Car Attached Garage * Tilt-in Insulated Double Pane Windows * Large Living / Dining Room Combo with Brick Accented Gas Fireplace * Updated Kitchen with Stainless Steel Appliances * Separate Laundry Room off Kitchen * 2 Generous Sized Upper Level Bedrooms + a Large Bathroom with Separate Make-Up Table. * Dual Zone Central Air, Dual Zone Hot Water Baseboard Heat * Full RV Hookup with Water, Sewer & Electric in Back Yard. *As Per 2021 Listing, 2011 BAT System Upgrade Allows For The Addition of a 3rd Bedroom* Conveniently located just minutes from all the shops and restaurants Chestertown has to offer, this quaint property offers a little rural lifestyle without the isolation!

Welcome to your tranquil retreat at Orchard Hill, where modern sophistication meets peaceful living on 1.89 acres of beautifully landscaped grounds. This stunning Cape Cod style home offers an abundance of amenities and thoughtful details throughout.As you step inside, you're greeted by the grandeur of vaulted ceilings that create an open and airy atmosphere. The ground floor primary bedroom provides convenience and luxury, complete with a upgraded kitchen featuring granite countertops, quality stainless steel appliances, an island with a gas cooktop, and a built-in wine refrigerator.The primary bedroom is a true sanctuary, featuring a luxury primary bath with a jetted tub and a stylish tile shower with glass doors. The main level's open layout is perfect for entertaining, with the added convenience of a bar with a sink.The second floor offers a guest bedroom, a full bath, and a loft that could easily be converted into a third bedroom or utilized as a versatile space according to your needs.Outdoor living is equally impressive, with a screened porch, large composite deck with a retractable canopy, a gazebo, and beautiful English cottage gardens featuring many native plants. The expansive outdoor space is perfect for gardening, outdoor activities, or simply enjoying the serene surroundings.Backing to trees and farmland, this property provides a peaceful backdrop and ample privacy. It's truly a must-see for those seeking a blend of modern luxury and peaceful countryside living. Schedule a showing today to experience the beauty and serenity of this exceptional property at Orchard Hill.