Chestertown MD Real Estate & Homes for Sale

Welcome to your dream home in the charming sought after community of Chester Harbor! This delightful property boasts 3 spacious bedrooms and 2 full updated bathrooms, perfectly designed for comfort and modern living. Step into the huge master bedroom, perfect for all buyers. The finished basement provides versatile additional living spaceâ??ideal for a family room, home office, or play area. The recently renovated kitchen is a culinary enthusiastâ??s dream, featuring contemporary finishes and high-end appliances that make meal prep a pleasure. Outside, the great yard is perfect for entertaining, gardening, or simply enjoying the serene surroundings. Enjoy the HUGE garage located in the rear of the property. Chester Harbor Community has a voluntary HOA ($30/year), which offers water access, a beach, community events, and a playground. Just around the corner is Round Top Park offering tennis, pickleball, and basket ball courts, a playground, and pavilion. Minutes from Chestertown's historic waterfront, restaurants, shopping, and marinas

Move-in ready and waiting for you! Start the new year in this charming 3-bedroom, 1-bath rancher. The brand-new kitchen is a showstopper, featuring sleek granite countertops, stylish new cabinets, and stainless steel appliances. Durable and attractive LVP flooring flows seamlessly throughout the home, creating a low-maintenance living space. Freshly painted from top to bottom, this home feels brand new. Enjoy your mornings or evenings on the new paver patio or front covered porch perfect for relaxing or entertaining and make use of the 8x8 shed for all your storage needs. With an HVAC system, roof, and BAT septic system just 9 years young, this home offers peace of mind for years to come. Situated in a water-oriented community, the optional $25 HOA grants access to community water privileges and park access. Conveniently located just minutes from Chestertown and within walking distance to Round Top Park, this is a must-see property! Whether you're starting fresh, downsizing, or seeking a perfect getaway spot, this home checks all the boxes. Schedule your showing today!

ð??¡ Just Renovated Creekside Beauty â?? Move-In Ready! ð??? Discover your dream home with this beautifully renovated 4-bedroom, 2.5-bath gem that overlooks a serene creek. Perfectly blending modern upgrades with cozy charm, this property has everything you need and more! â?¨ Key Features: Spacious 2-Car Garage Bonus Room: Use as a 4th bedroom, home office, or entertainment haven! Brand New Roof for peace of mind. Updated Bathrooms with modern finishes. Fully renovated kitchen with quartz countertops and stainless steel appliances. New HVAC systems with dual zones for ultimate comfort upstairs and downstairs. All New Flooring and freshly painted throughout. Step outside to enjoy your restored decks with stunning water views â?? perfect for relaxing or entertaining. Conveniently located near shopping, restaurants, and more! Donâ??t miss this opportunity to own a slice of paradise. Schedule your showing today! ð??¡â?¨

Need additional space, no problem! This home has a sunken den with a brick wood fireplace off the main living room that could be used as an office and a humongous 23â??8 X 18â??4 family room currently used as the Billards room hosting a 9ft pool table/gym off the kitchen/dinning room that was added in 2021! This room is great for entertaining & hosting large parties and could be a fantastic place to have a daycare! A voluntary HOA allows access to the communities private beach, dock and playground all located on Rosin Creek with access to the Chester River! We are running late on getting our professional photos! So sorry for the delay!

Lovely all one floor living in quiet neighborhood with updated features throughout! Brand new gorgeous kitchen with white shaker cabinetry featuring dovetail construction soft close drawers, solid butcher block countertops, tile backsplash, large island, brand new stainless steel appliances and much more! eng hardwood flooring, recessed lighting, vertical custom ship lap, gas fireplace, screened porch opportunity and much much more! ABSOLUTE MUST SEE MOVE IN READY HOME!

Welcome to Chester Harbor. Great 3 bed 2 bath rancher awaits new owners. The floor plan includes generous Eat -in kitchen and large living room, separate laundry, and a huge screened in porch for picking crabs, parties, or just relaxing. New flooring , fresh paint, and new kitchen counters are a few of the recent updates. Tree lined rear yard and front holly hedge provide surprising privacy. Close to Historic Chestertown and many local points of interest. Voluntary HOA is $25 a year and provides for community water access and park privileges. Shed is " AS IS". Open House January 11th (12- 2 PM.)

Ring in the New Year at 23315 Sandpiper! Nestled quietly within the water-oriented community of Chesapeake Landing and within walking distance to picturesque views of Worton Creek. Established in-between multiple ramps and marinas, providing convenient access to the Chesapeake Bay and many of its tributaries. The surrounding woods, open field and neighboring pond offer peace in nature with an abundance of wildlife found throughout. Enjoy peaceful mornings on the easterly facing front porch or unwind on the open side deck. Inside you'll notice natural light gleaming throughout with unique features that will make this home stand out from the rest. Spotlighting a spiral staircase as your center piece while galvanized tray ceilings elegantly accent the living area. This 2 bed, 2 bath home is move in ready and comes equipped with a fully encapsulated crawlspace, tankless hot water heater, spacious laundry area with washer/dryer and kitchen that conveys all appliances.

Brick rancher located on the corner of Greenwood and Glen Street in College Heights offers a large screened porch, eat-in kitchen and dining room. Home is convenient to downtown historic Chestertown , Washington College and hospital. Property is served with public water/sewer. Underground oil tank has been removed and the crawlspace is encapsulated.

OWN FOR LESS THAN THE COST OF RENTING. Built in 2005, this beautifully maintained home offers modern comforts and an inviting atmosphere. The open floor plan on the main level features bright, airy spaces that seamlessly connect to a charming brick patio via sliding glass doors. With 3 bedrooms, 2.5 bathrooms, and 1,222 square feet of low-maintenance living, this home is designed for ease and comfort. Enjoy the convenience of two dedicated parking spaces right at your doorstep and the peace of mind that comes with no outdoor upkeep. The spacious living and dining areas flow effortlessly to the rear porch and shared common grounds, creating the perfect setting for relaxation or entertaining. Nestled in Chestertown, this home is ideally located near Washington College, Chester River Hospital Center, and the Chestertown walking trail, offering easy access to both local amenities and recreational opportunities.

Welcome to Chester Harbor - a family oriented place to live! The Chester Harbor Community has a voluntary HOA of $30/year, which offers water access, a beach, community events, and a playground. Close by is Round Top Park offering tennis, pickleball, and basketball courts, a playground, and a pavilion. Minutes from Chestertown's historic waterfront, restaurants, shopping, and marinas. Queen Annes County Schools! Comfortable serene and convenient - this well cared for home has hardwood floors and a new hot water heater and water tank on 3/11/2023 and an attached workshop!

Brand New Gorgeous Custom Home ready Jan 12. CLOSING HELP for acceptable contract! Fall in love with the 1st floor bedroom/bath/WIC, 2 car garage, gourmet kitchen with large island & granite counters, cathedral ceilings, huge family room, 1st floor laundry, front porch, sky-basement on 2nd floor for storage, 2 large bedrooms and full bath on second floor. This great floor plan is hard to find with all of these upgrades and is perfectly situated on an acre lot in a beautiful country setting. Relax and watch the sun rise or set as you boast to your family & friends about this amazing house you just bought. Great country location near the Chester River, boat ramps, beaches, parks, hospitals, restaurants, shopping. Convenient to the beaches, Dover, Middletown, Annapolis & DC/Balt. Won't last long! Co-owner/RE agent.

Rare end unit townhome in Oak Hollow. Close to shopping and college. Spacious rooms. Open kitchen with granite counters and a kitchen island. Sliders to patio and to upper level deck. Large yard. Half bath on the main floor. 3 bedrooms and 2 full baths on the upper floor. Family room in the basement as well as an oversized 1 car garage with lots of storage. Roof has recently been replaced. Overall, a great unit in a great location!

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 unofficial bedroom in the basement, thereâ??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, 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. Interior pictures and layout coming soon!

This impeccably maintained home is a true standout and has it ALL! With 5 spacious bedrooms - with both main level & upper level primary suites - and 3.5 baths, including a main level primary suite with a walk-in closet featuring a premium wood built-in system, dual vanity, and a double-headed walk-in tiled shower. This home offers both luxury and convenience. The updated kitchen is an ideal space, with granite countertops, stainless steel appliances, a stylish tile backsplash, and 2015 KraftMaid cabinetry in a stunning navy blue. Every room is thoughtfully painted and wallpapered, adding character to the gleaming hardwood floors and plush, high-quality carpets throughout. The home also boasts an updated HVAC system and a brand new asphalt driveway. The basement includes a rec room and ample storage space, while the expansive 0.8-acre lot overlooks serene pastoral farmland, with a beautiful hardscaped patio perfect for outdoor entertaining. Best of all, this home is located under 1.5 miles from the heart of downtown Chestertown, so youâ??re just minutes away from shopping, dining, and all the charm the town has to offer.

A highly coveted Chester River waterfront just minutes from Historic Downtown Chestertown. This large home has an ample sunroom overlooking the yard to the Riverfront, an in-ground pool within the 100' buffer, a dock with 3+ MLW, an expansive primary suite with sweeping water views, a private space for a home office, playroom, or in-law suite, and a detached three car garage for toys, vehicles, and storage. All situated on almost one full acre. Brand new upgrades since Sept '24 include central AC, roof, refinished hardwood floors, and paint throughout. With easy access to Morgnec Rd, Rt. 301 is only 12 minutes away... which leaves you only an hour's drive from Wilmington, DE or Philadelphia, PA. And into the heart of NYC in less than three hours. Escape to the Eastern Shore lifestyle!

Adorable and Affordable in Chester Harbor community! This 4-bedroom 2 bath home is ready for you! situated on a .8-acre level lot that backs to trees and open fields, this home offers a private retreat in a sought-after Water oriented community. There is a large Country Kitchen with room for table and chairs. Laundry in Kitchen is convenient and easy to access. Main level has two bedrooms and 2 baths while the finished lower level offers plenty of space and 2 bedrooms. Come and enjoy the tranquil and walkable neighborhood that is close to Chestertown and offers Queen Annes County Schools!

Welcome home to this beautiful end unit townhome in the newer community of The Village At Chestertown. This 3 bedroom, 2.5 bath townhome looks out over the beautiful pond with fountain, and a great walking path around the pond and community. Furry friends are welcome at the nearby dog park as well. This home is less than a year old and has had some upgrades added since the purchase, such as the maintenance free fully fenced back yard, ceiling fans, upgraded light fixtures, upgraded bathroom vanities, kitchen faucet, hardware, and more! Easy commute to Rt. 301, and the brand new YMCA is right around the corner! Enjoy Chestertown with it's small town charm, great restaurants, artistic venues, and close to Washington College. Schedule your tour today!

Welcome to this lovely home with a detached garage in the community of Woods Edge in Kent County! The home features three spacious bedrooms with built-in closets, a full bath with dual vanities and a soaking tub, a family room with a fireplace that opens to the kitchen with appliances and wooden cabinets, and a sunroom with tiled floors and a sliding door that leads to the backyard. The home is located near the Chesapeake Bay and is just a 10-minute drive to the beaches and marina. Additionally, it is 9 minutes away from the ACME market and local restaurants.

This fabulous craftsman style 3 bedroom home, is perfectly situated to enjoy the beauty and tranquility of the East fork of Langford Creek/Bay with approximately 150' of shoreline and sandy beach. Great room was added in 2001, with a loft and cat walk to offer added living area. Updated kitchen in 2022 The subject property is one of 5 waterfront properties that belong in the Cacaway Farm Cooperative Housing Corporation, an exclusive farm housing community. Experience the same benefits of a fee simple ownership but share the cost of expenses. Enjoy privacy and the use of your own waterfront with sandy beach by way of a gentle slope to the water, launching kayaks or canoes while deep water slip at the community dock is also included. A south facing direction on the water side offers wonderful & welcoming breezes throughout the summer. It is improved by 2 car heated garage built in 2006 plus a smaller area for storage with a bonus area above. The area above has radiant floor heat. A BAT septic was installed in last 4 years, with a new shared sewage disposal area maintained by the county. Please do not drive down Cacaway Farm Lane without an appointment. This is a private lane.

EXCEPTIONAL VALUE-This charming Cape Cod home offers exceptional value with a recent $10,000 price reduction and new carpet throughout. Located on a desirable corner lot in Kingstown, this property is just a short walk or bike ride from historic Chestertown. The home features a modernized kitchen, updated bathrooms, and custom tile floors. Enjoy the convenience of a first-floor bedroom, a spacious living room, and a combined dining/family room. The second floor includes two additional bedrooms and a full bath. Outside, a private backyard with a 14 x 10 deck and privacy fence provides a peaceful retreat. The oversized three-car detached garage, with approximately 900 sq ft of space, comes equipped with a storage loft and newly installed electric. While the property is addressed as Chestertown, it is actually situated on the Queen Anne's County side of the Chester River. The area offers a wealth of activities, including a weekly farmers market, local events, boating, dining, shopping, and easy access to the YMCA. Plus, it's conveniently close to Washington College, enriching the community's vibrant atmosphere. This is a fantastic opportunity to own a lovely, well-maintained home in a prime location!

Welcome to 116 Pine Chip Road, a beautifully renovated Cape Cod in the heart of Chestertown, MD, Queen Anne's County. This 3-bedroom, 1 1/2-bathroom home has undergone a complete transformation, boasting new siding, windows, doors, and drywall throughout. The modern upgrades continue inside, where you'll find stunning LVP flooring on all three levels. The main level features two spacious bedrooms, each with double closets, and a full bathroom. The custom kitchen is a chef's dream, featuring a gas stove, upgraded quartz countertops, solid wood cabinets, and stylish open shelving. Upstairs, the primary bedroom offers a private retreat with a mini-split AC/heat unit, a large dressing room, and a convenient 1/2 bath. The finished basement is perfect for entertaining, complete with surround sound, a laundry room, and a utility room. The outdoor space is equally impressive, with a newly installed privacy fence surrounding the backyard. The fence includes three personal gates and one large gate for vehicle access. Additionally, the property features a shed and a detached garage, providing ample storage and workspace. This home is move-in ready and offers a perfect blend of modern amenities and classic charm. Don't miss the opportunity to make 116 Pine Chip Road your new home!

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.

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

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.

Discover 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. Boat Slips are Available for lease or purchase. 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. Open room on first floor could be used for a third bedroom for guests. 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. 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!