Chestertown MD Real Estate & Homes for Sale

Fresh new look to this townhome includes fresh paint, new carpet and new HVAC system. Looking for an affordable option to paying rent? This two bedroom townhouse is just the answer. Close to the Bay and all Tolchester offers from it's marina, Shanty beach bar and the best spot for an incredible sunset. Tolchester Village offers the perfect location for those looking for a summer retreat or full time residence. Don't sleep on the boat when you can afford to own on land. Just minutes to Rock Hall and Historic Chestertown.

Nestled in a prime suburban commercial zone, this versatile property offers 1,300 sq ft of living space, perfect for both residential and/or commercial use. The freshly resealed driveway accommodates up to 6+ vehicles, with the potential for parking lot expansion, ensuring ample space for guests or clients. The property features two inviting front entries: one through an 8x16 sunporch, ideal for enjoying morning coffee or greeting visitors, and another through the welcoming living room with a large bay window that floods the space with natural light. The rear entry provides convenient access to the kitchen and basement. The kitchen is equipped with all essential appliances and features laminate countertops and durable vinyl flooring. A pass-through window connects the kitchen to the sunroom, enhancing the open and airy feel of the building. The basement, with its poured concrete floor and perimeter trench leading to the sump pump, offers potential for additional storage or workspace. The single level structure includes a spacious full bath and three generously sized bedrooms, perfect for a family or for converting into office spaces. This property blends functionality and charm, making it a unique opportunity for those looking to live and work in a suburban setting.

This exquisitely renovated 1800s home showcases the timeless elegance of its original architecture. Every detail has been restored to its former glory. No expense has been spared in selecting the finest finishes and materials for this renovation and it extends beyond the interior, with the creation of an outdoor oasis. This meticulously landscaped gardens and charming patio provide a private retreat right in the heart of Historic Downtown Chestertown. Chestertown is conveniently located on Maryland's Eastern Shore, less 80 miles from Washington DC and 90 miles from Philadelphia

This exquisitely renovated 1800s 2 Bedroom home showcases the timeless elegance of its original architecture. Every detail has been restored to its former glory with preserving its charm and character of its historic roots while incorporating modern updates for a truly exception living experience. Located in the heart of Chestertown with very easy walk to shops, restaurants, parks and just two blocks from the Chester River waterfront. Chestertown is conveniently located on Maryland's Eastern Shore, less 80 miles from Washington DC and 90 miles from Philadelphia

Built in 2005, this like-new home boasts an open floor plan with inviting, bright spaces. The residence features 3 bedrooms, 2.5 bathrooms, and 1,222 square feet of low-maintenance living. Enjoy the convenience of two dedicated parking spots right in front of the home, as well as no outside maintenance. The half bath comes equipped with a stacked washer and dryer for added ease. The spacious living room and dining room seamlessly flow to a sliding door that opens to a rear porch and common grounds, perfect for relaxing or entertaining. Located in Chestertown, this home is in close proximity to Washington College, Chester River Hospital Center, and the Chestertown walking trail, making it an ideal location for both convenience and leisure.

Charming Historic Chestertown investment opportunity! Once updated this building can accommodate two street-front shops and a spacious apartment upstairs. The back of the building has extra living space with a private entrance and full bathroom. The attic is flooded with natural light! One could use the attic as-is for extra storage, or it could be renovated, adding additional living space. Back deck overlooks sweet courtyard, perfect for relaxing. GREAT location and tons of character - enjoy the Chestertown Farmer's Market year round, the Chester River just a few blocks away, shops and restaurants right down the street - you cannot beat this Historic District location and opportunity. Seller has removed plaster walls downstairs and updated the electric. Other updates include: exterior painting, new metal roof and a new deck with entry to second floor apartment.

Coming Soon! Charming 2-Bedroom Home on 1 Acre with Scenic Farm Views! Welcome to your dream retreat! This delightful 2-bedroom, 1-bathroom home offers a perfect blend of comfort and charm, nestled on just over 1 acre of lush greenery. As you step inside, youâll be greeted by a spacious formal living room that invites relaxation and gatherings with loved ones. The eat-in kitchen is a cozy space, perfect for casual meals and culinary creativity, while the sun porch provides a bright, cheerful spot to enjoy your morning coffee or unwind with a good book. For those lovely evenings, the screened-in sun porch allows you to soak in the gentle breezes without the worry of pesky insects. With expansive outdoor space and picturesque views of the adjacent farm, this property is ideal for anyone seeking tranquility and a connection to nature. Donât miss your chance to own this charming home in a serene setting!

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

Spec home located in small 12 home development (to be built). Prestwick offers the best in eastern shore living with the small town charm of Chestertown, MD, yet only 1 to 2 hours from Wilmington, Philadelphia, Baltimore and Washington, DC. Join the club and have access to the great golfing, club pool, marina (with boat slips) and boat ramp or just launch the boat, paddle board or kayak at the new town marina or the many county owned ramps. Design and build the home you want with one of the area's finest builders

Park like setting with natural beauty all around you, take a quite day with very nice outdoor den . Watch the herons, eagles, ducks and geese search for food or take a leisurely kayak cruise down Mill Creek to the Chesapeake Bay. Conveniently located a short distance from Worton Creek Marina, Restaurants, Resort Style Marinas, Historic Chestertown, Parks and much more. Chesapeake Landing Offers water access with 2 marinas, boat slips and docks. A perfect location to keep for a weekend away on the beautiful Eastern Shore or primary residence.

Completely remodeled, this three-bedroom waterfront home boasts a charming front porch and enormous back porch - your private space overlooking the river - along with an enclosed sunroom featuring gorgeous river views through walls of windows. Enjoy abundant outdoor areas and stunning water views from nearly every room. The dock features 3+ feel MLW, with slips available for purchase. This condominium embodies the ideal waterfront living experience. Located in the heart of historic Chestertown, this unique property includes off-street parking and provides the convenience of walking into town for dining and shopping. Situated on Maryland's scenic Eastern Shore, it's less than 85 miles from Washington D.C. and Philadelphia, making it a perfect meeting spot for those in the Mid-Atlantic region.

Welcome to 209 Princess Anne Drive, a delightful 3-bedroom, 2-bathroom home nestled on a double lot in the heart of Chestertown, Maryland. As you step into the grand foyer, you'll immediately appreciate the spaciousness and elegance this home offers. This meticulously maintained residence boasts three comfortable bedrooms that provide ample space for relaxation and privacy. The property also features a shed equipped with camper hook-ups, perfect for outdoor enthusiasts or additional storage needs. The two-car garage offers both convenience and security for your vehicles and belongings. Outdoor living is a highlight of this home, with a back deck and patio space perfect for entertaining or unwinding after a long day. Additionally, the centrally located utility room ensures easy access and convenience for your daily chores. Situated in a desirable neighborhood, this home is close to Chestertown's charming downtown, shops, restaurants, and scenic views of the Chester River. Don't miss the opportunity to make this lovely property your new home! Schedule your private showing today!

Discover the epitome of luxury living in this exquisite townhome nestled within the prestigious water-oriented community of Chester River Landing. Designed with elegance and comfort in mind, this residence offers an unparalleled lifestyle that combines sophistication with the serene beauty of waterfront community living. The heart of the home, the open kitchen is designed for both functionality and style. It features sleek countertops, ample cabinet space, and a large island that doubles as a breakfast bar, making it perfect for meal preparation and casual dining. Enjoy the convenience and efficiency of top-of-the-line appliances throughout the home, including a stainless steel refrigerator, oven and dishwasher. Enjoy the sunset from the upper deck or below on the screened in porch by the pond with fountain. The porch was renovated this spring with high tech flex screens and ceiling was waterproofed providing for increased time for usage while keeping the area dry. This property is only 1 of 2 units with screened in porches. Chester River Landing is nestled along the serene Chester River, this charming waterfront community exudes a perfect blend of relaxation and recreational opportunities. The centerpiece of the community is a picturesque floating pier that gently sways with the rhythm of the water. This well-maintained pier offers numerous available slips, making it an ideal haven for boating enthusiasts who enjoy easy access to their watercraft. Enjoy the community pool during the day then take in the sunset on the pier with picnic tables and a gas grille. As the day transitions into evening, the fire pit area becomes a popular gathering spot. Encircled by cozy adirondack chairs, the fire pit offers a warm and inviting ambiance, perfect for sharing stories, roasting marshmallows, and enjoying the company of neighbors under the starlit sky. All of this while located in the Historic Town of Chestertown, known for its waterfront charm, restaurants, and weekend festivals! Don't miss your chance to make this remarkable property your own! Ensuite windows will be replace with new insulated double pane windows end of July!

Enjoy picturesque water views of Worton Creek from every room. Situated on over 2.5 acres of well maintained and landscaped property with irrigation and enjoy the water from the private pier with 5 ft. of depth and only minutes by boat to the Chesapeake Bay or relax by the water side pool. This five bedroom three bath home has an apartment above the detached 3 car garage with a full kitchen, living room and bedroom. The bright and open main level boast hardwood floors throughout a beautiful kitchen with central island, bosch refrigerator, dishwasher and gas stove top with double DeCor convection ovens. The living and dining rooms have cathedral ceilings and a gas fireplace. The primary suite is on one side of the house with a gas fireplace. The bathroom has a steam shower. There is a solar system on the barn roof producing 25% of the energy needs. Completing this must see property is a large barn that the first level has been converted to a multi purpose room. The second floor of the barn is unfinished with 24 ft. high cathedral ceiling and awaits your imagination to convert it to special living space or use it as is for storage. Just a few minutes down the road to Chestertown and Rock Hall and an easy drive to Annapolis, BWI, DC and Philadelphia.

Welcome home to this 3 BR 2 bath home in Kingstown Manor, situated on 1/2 acre just seconds from the Chester River. Newly refinished flooring throughout! The gorgeous, custom tiled backsplash, updated kitchen includes stainless steel appliances and is open to the dining area with built in bench seating. From the dining area you can exit the rear door onto the patio overlooking the fenced backyard with mature trees. Cased openings separate the kitchen and dining from the living room with adjoining office. Both the primary and hall baths are updated with custom tiled showers. Updates to the home also include roof, septic, HVAC, windows, doors and water softener with reverse osmosis.

Where Shore living begins! This well maintained home is established within the quiet subdivision of Kingstowne Manor. Located just on the Queen Anne's County side of the Chester River Bridge, this location offers opportunities from both Kent and Queen Anne's Counties. Just minutes from the heart of Historic Chestertown where you'll find plenty to discover through the Local Shops & Restaurants, weekly Farmers Market, Parks for Recreation and many Events throughout the year. You can fly your flag proudly as you pull into 201 Princess Anne. The asphalt drive will provide a smooth transition home and offer you plenty of area for parking. Bring your boat for quick access to the serene Chester River. By either remote or mobile app, you can open the overhead door to access this homes attached garage. It will provide ample space to keep your vehicles, toys or projects out of the weather and well protected. Equipped with a propane heater and 220 AMP service, you can comfortably stay busy year round. Stepping inside, the home offers over 2,000 square feet with 3 bedrooms, 2 baths and is established on over 3/4 of an acre. The homes attic is also fully floored for all of your storage needs! This spacious kitchen provides under cabinet lightening, beautifully crafted seamless quartz countertops and conveys all kitchen appliances. The Living Room and Primary Bedroom both provide options for electric baseboard heat. New carpeting in Primary was installed April of 2024. Stepping outside, you'll be offered plenty of backyard seating and privacy from mature surrounding trees. Relax from your day underneath the recently installed gazebo. The patio here will provide ample space for grilling and gathering. Fenced in back yard provides a worry free option to allow your children (four legged or two) to play freely. A new roof system was installed April of 2024. This system has a transferable 10 year warranty! Home is equipped with top of the line Fiber Optic Internet services. The Septic System has also been updated with an additional 80' drain field to support any of your in home services.

Charming Renovated Ranch Home in Tolchester Estates Welcome to this beautifully renovated ranch home nestled in Tolchester Estates. Recently updated, this home offers a perfect blend of modern amenities and tranquil surroundings. As you step inside, you'll notice the new flooring throughout and fresh paint that creates a bright and inviting atmosphere. The remodeled kitchen is a chef's delight, featuring brand new cabinets, elegant granite countertops, and sparkling stainless steel appliances. The spacious master bedroom boasts an en suite bathroom, providing a private retreat within your own home. Both bathrooms have been tastefully updated with contemporary fixtures and finishes. Additional recent upgrades include a new roof, ensuring peace of mind for years to come, and a new heater and air conditioner for ultimate comfort throughout the seasons. Situated in a secluded setting, this property offers privacy, perfect for relaxation and enjoying the natural surroundings. Its proximity to the water adds to the appeal, making it ideal for water enthusiasts or those seeking a serene coastal lifestyle. Don't miss out on the opportunity to make this renovated ranch home yours. Schedule a showing today and envision yourself living in this peaceful retreat in Tolchester Estates. Owner is a licensed Realtor.

Come By this brand new Cape Cod nestled in charming Pear Tree Point! This 3-bedroom, 3-bathroom haven offers the tranquility of coastal living with the ease of new construction. Step inside and discover the warmth of this open floor plan luxury vinyl plank flooring flowing throughout the main level. Unwind in the light-filled living area, perfect for entertaining, or retreat to the inviting main-floor primary bedroom suite, designed for ultimate relaxation. This private sanctuary boasts an attached bathroom with modern fixtures and finishes, and spacious walk-in closets. Unleash your inner chef in the stunning kitchen, featuring stylish shaker cabinets, gleaming granite countertops, and a suite of stainless-steel appliances. Extend your living space onto the expansive patio, perfect for al fresco dining or simply soaking up the tranquility of your waterfront surroundings. Modern finishes throughout and ample storage space completes this lovely home. But the best part? SPECIAL FINANCING options with discounted interest rates, low monthly payments, and low-down payment options make this dream a reality! Pear Tree Point offers a vibrant community atmosphere with water access, marinas, and nearby parks. Don't miss this opportunity to own a brand-new waterfront haven! Contact us today to schedule your private showing.

Looking for extra space? This home has a large extra room that could be a primary bedroom & bath with walk in closet, a den/playroom, office with a separate private entrance, gym or whatever your lifestyle is in need of! The original primary bedroom includes an attached half bath and the original hardwood floors gleam throughout most of the home! Easy access to multiple public ramps & just a short drive to Downtown Chestertown, this .55 acre home is ready for you to make it your own! *Current HVAC needs refrigerant, a Bryant 15 seer 3 ton AC is estimated to be $9,000! Credit for cost to replace or a reduction in price can be neogtiated*

Investor Alert! A rare opportunity to own a piece of History in down town Chestertown! This home has been a very lucrative rental for the past 10 years which you can easily add to your portfolio or rennovate and bring it back to its glory! One of the few homes on High Street to come with off street parking (up to 4 spaces) accessed by alley way in back. Partially fenced in back yard with privacy and open sunny deck. Nice covered front porch. Inside is boasting with original charm! Original wood floors throughout most rooms. A large eat in kitchen with breakfast nook , overlooking private back yard. Original Sash windows, cedar shingles, and metal roof. Lead Paint Certification. This home has so much potential!

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 chefâs 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, youâll 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 communityâs 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. Donât 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 â 4 bedrooms, 2.5 baths, a spacious living room, and a large kitchen makes this home irresistible â 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.

This stunning renovation is the jewel of Chestertown's revitalized upper historic district! A beautiful view of Washington College (9th best college in the country by Princeton Review), invites a walk around campus, to the river, or to downtown shops & restaurants. This home is conveniently located so that a short three blocks takes you to the new Starbucks⦠yay coffee with friends!ÂExtensive interior & exterior renovations along with plumbing, mechanical, and electrical upgrades throughout make the beauty of this stunning home more than just looks! Possible owner financing with attractive rates could make it yours! The redesigned layout and flow is comfortable and elegant: Located on the first floor off the center hall, is the living room, dining room, kitchen, den/office, half bath, all-season sun room. The new custom kitchen showcases an individually handcrafted brick floor and imported Spanish tiled backsplash. The original grand stairway leads to the second floor and a cozy sitting area  at the end of the catwalk. The primary bedroom includes a five piece luxury en-suite bath, while two additional bedrooms share a full hall bathroom. The dedicated laundry room, has storage cabinets, room for ironing and folding and a cleaning supply niche The spacious third floor garret-studio has an independent climate control, a full bathroom and an L-shaped cooking & dining counter. A comfortable sitting area, dedicated sleeping/dressing space and a study nook complete this floor. A desirable rear alley, leads to the home's private off-street parking spaces and the carriage-styled garage which can accommodate an SUV. Need even more storage or extra rooms? Easily access to the 1100 square ft basement with 7.5â ceilings from an exterior doorway off the patio or from inside the home. This property is fully fenced & gated providing privacy for outdoor activities and security for family and pets. This brick colonial Âhas been extensively renovated and is turn-key! Square footage is estimated: buyer to verify. A complete upgrade record is available upon request.