The median home value in Chestertown, MD is $370,247.
This is
higher than
the county median home value of $301,300.
The national median home value is $338,100.
The average price of homes sold in Chestertown, MD is $370,247.
Approximately 42.33% of Chestertown homes are owned,
compared to 50.71% rented, while
6.96% are vacant.
Chestertown real estate listings include condos, townhomes, and single family homes for sale.
Commercial properties are also available.
If you see a property you’re interested in, contact a Chestertown real estate agent to arrange a tour today!
Prime 1.05-Acre Vacant Land in Chestertown, MD! Located at 206 Burchard Sawmill Rd, this versatile property offers a fantastic opportunity to build your dream home or investment property in a peaceful, scenic setting. Surrounded by natural beauty and close to local amenities, this lot provides both privacy and convenience. Don’t miss out on this rare chance to own land in historic Chestertown!
Welcome to this charming 3-bedroom, 2-bathroom rancher, offering the perfect blend of comfort and convenience with one-level living in the desirable Chester Harbor community. Set on a spacious .76-acre lot on the Queen Anne's side of the Chester River, this home is ideally situated in a water-oriented neighborhood, perfect for boating enthusiasts and nature lovers alike. The home boasts a large primary bedroom with its own private bath and an impressive walk-in closet, which includes a cedar section for added storage and warmth. The kitchen and dining area, featuring newer flooring (installed just two years ago), create a modern, inviting space for meals and family gatherings. The kitchen is equipped with updated appliances, ensuring a functional and stylish area for cooking. Outside, the fenced yard—perfect for both kids (two- or four-legged)—provides a safe and spacious environment to play and explore. The fence, installed just four years ago, adds a secure touch to the property. Additionally, the detached two-car garage offers ample storage for vehicles, tools, or water toys.
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? 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 oriented haven! Contact us today to schedule your private showing .****Special Discounted Financing in available for this home, with rates are available**** Contact for details, rates subject to change, subject to loan qualification.
This end unit waterfront condo in Scott's Point has beautiful water views up and down the Chester River! It is a light filled gem with water views from every window. It has been impeccably maintained and offers wood floors, fireplace, plantation shutters, gourmet kitchen, front and back porches, second and third floor balconies and much more. There are two deeded slips (4ft. MLW) at the community dock, one with a 7 1/2 ton lift. The first floor open floor plan has a kitchen, living room, dinning area, den and half bath. The master bedroom and bath are on the second floor with two walk in closets. There is also a laundry room and home office. The third floor has two bedrooms, two full bathrooms and a sitting room with kitchen conveniences. There is plenty of storage on all three levels. Come and enjoy the water, the views and the conveniences of living in historic Chestertown!
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 space—ideal for a family room, home office, or play area. The recently renovated kitchen is a culinary enthusiast’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!
? Just Renovated Creekside Beauty – Move-In Ready! ? 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! ? 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 – perfect for relaxing or entertaining. Conveniently located near shopping, restaurants, and more! Don’t miss this opportunity to own a slice of paradise. Schedule your showing today! ??
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 23’8 X 18’4 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! Va loan has an assemble low interest rate for those who qualify for VA!
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!
ONLINE AUCTION: Bidding begins 2/5/2025 @ 10:00 AM. Bidding ends 2/7/2025 @ 12:20 PM. List Price is Suggested Opening Bid. Lot of Land located in Chestertown, Maryland within Kent County. Property is in close proximity to all the attractions in Chestertown, Maryland. Property is Vacant. Easy Access to Major Traffic Artery Chestertown Road. Deposit: $5,000.
ONLINE AUCTION: Bidding begins 2/5/2025 @ 10:00 AM. Bidding ends 2/7/2025 @ 12:25 PM. List Price is Suggested Opening Bid. Lot of Land located in Chestertown, Maryland within Kent County. Property is in close proximity to all the attractions in Chestertown, Maryland. Property is Vacant. Easy Access to Major Traffic Artery Chestertown Road. Deposit: $5,000.
ONLINE AUCTION: Bidding begins 02/05/2025 @ 10:00 AM. Bidding ends 02/07/2025 @ 12:20 PM. List Price is Suggested Opening Bid. Lot of Land located in Chestertown, Maryland within Kent County. Property is in close proximity to all the attractions in Chestertown, Maryland. Property is Vacant. Easy Access to Major Traffic Artery Chestertown Road Deposit: $5,000.
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.)
Discover serenity in this charming 2-bedroom, 2-bath oasis with 1,272 sq ft of living space. Nestled in the Chesapeake Landing community, enjoy proximity to Worton Creek's stunning views and easy access to the Chesapeake Bay. This home boasts enchanting features, including a captivating spiral staircase and elegant galvanized tray ceilings that enhance the vibrant, light-filled living area. Relax on the easterly front porch or open side deck, surrounded by nature's beauty and wildlife. With a fully encapsulated crawlspace, tankless hot water heater, and a well-equipped kitchen, this home is truly move-in ready for your peaceful Eastern Shore retreat.
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.
An adorable cottage with water views of the Chester River! Nicely maintained cottage featuring 3 bedrooms, 2 full baths with all the big ticket items completed. Newer Well and Septic, HVAC and newer Metal Roof just leaves you with finishing touches on the interior as you see fit. Currently used as a rental. Also features a detached workshop and detached garage. If you are a boater, bring your boat and the Deep Landing Boat Ramp is just minutes away . Very affordable home in our area, don't wait on this one!
This prime commercial lot offers an exceptional opportunity for your next business venture. Situated on Haacke Drive, this 0.96+/ -acre parcel is zoned C-1, which allows for a variety of commercial uses. With limited commercial land available in the town and county, this is a rare find in a desirable location with great potential for visibility and customer traffic. There is also potential for R-4 (Residential) zoning, depending on the town's planning and zoning approval. Ideal for retail, office space, or service-oriented businesses, the property is ready for development. Buyers are encouraged to check with the town regarding specific zoning regulations, potential use, and public water/sewer hook-up fees to ensure a smooth development process. Whether you’re looking to expand your business or invest in a growing area, this lot offers the perfect foundation for success. Don’t miss out on this rare opportunity!
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!
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.
This meticulously maintained 3-bedroom, 2-bathroom ranch-style home offers the perfect blend of comfort and modern features. Located in a tranquil setting that backs to farmland, it boasts an open floor plan with cathedral ceilings, creating a spacious and airy atmosphere throughout. The upgraded kitchen with stainless steel appliances that make it ideal for both cooking and entertaining. The upgraded flooring adds elegance and durability to the home, while the energy-efficient tankless water heater ensures a continuous supply of hot water. Whether you're relaxing in the living area, enjoying the views of the surrounding farmland, or hosting guest in the open space, this home is designed for modern living. It's truly a must-see for anyone seeking a move-in ready home. 1 acre lot
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 19. CLOSING HELP for acceptable contract & all reasonable offers considered! 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. Co-owner/RE agent.
