The median home value in Chestertown, MD is $245,000.
the county median home value of $183,500.
The national median home value is $185,800.
The average price of homes sold in Chestertown, MD is $245,000.
Approximately 41.87% of Chestertown homes are owned,
compared to 42.32% rented, while
15.82% 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!
Learn more about Chestertown Real Estate.
The location of the main house, 3 cottages, in-ground pool & pool house in the critical area buffer make this waterfront compound offering one that is extraordinary and extremely rare. Situated on the banks of Comegys Bight roughly 7.5 miles from Historic Chestertown is a 51.55-acre whimsical oasis with nature & riding trails, pastures, barns, farmland, woodlands... make this your Camelot...
This property is private, secluded and beautiful waterfront. It also includes another lot which will be transferred which is 1.15 AC. Cute cottage, in good condition, featuring an enclosed porch with a deck. Beautiful water front with a private dock and beach. Not much exterior maintenance, or interior maintenance needed. Just come and enjoy life on Fairlee Creek.
Do I have the girl for you! She's a bit old-fashioned, but she has solid bones. This 3 BR brick rancher, set amidst flowering shrubs on a quiet street in College Heights, offers a country size sunlit kitchen, polished hardwood floors, wood burning fireplace, double pane windows and a 1-car attached garage. All within walking distance to everything Chestertown has to offer; Washington College, restaurants, local shops, new marina and much more. Check her out and see what comfortable living is all about!
Custom built home on the market for the first time! The open floor plan has 2 story living room. Balcony on the 2nd floor to bedrooms. Warm Honey tone wood details, mantel, and trim create a very inviting atmosphere. Wonderful home backs up to the stream that offers great views of birds and nature while providing privacy. Enjoy the screened-in porch in the warm weather or snuggle by the fireplace on cold evenings.A prestigeous neighborhood close to the Country Club, golfing, boating and downtown Chestertown!
This 1536 sq foot home, sitting on a large lot in Tolchester Estates, has lots of potential! With a dry crawl space, all systems in good working condition, and recently inspected and maintained roof. Complete with two porches, water views, and a community beach with boat ramp only blocks away.
Eastern Shore Farm set on 22 acres in a private setting is a true gem conveniently located just 2 miles from downtown Chestertown. The pristine horse farm has a 6-stall horse barn with hay loft, tack room and workshop. There is also two run-in sheds, machinery shed, an 8 acre hay field, and 10 acres of fenced pasture. Amenities enhancing the property include a stream with bass, a pergola, vegetable and flower gardens. Surrounded by mature landscaping, the 3 bedroom country home offers pastoral views, a first floor bedroom and full bath, and bright open kitchen. Anchored by a beautiful raised hearth fireplace, the living room opens to the screened porch. Founded in 1706, Chestertown is a picturesque walking town set on the banks of the Chester River with 18th century homes, cafes, pubs, galleries and shops. Enjoy the Chester River Walk, waterfront dining and marina or take a river cruise on the Chester River Packet. Residents enjoy the vibrant arts community, parks, walking trails and water activities. Annual events include the Chestertown Tea Party and Tall Ship Downrigging Weekend. Chestertown is also home to Washington College. Located about 90-minutes from Washington and Philadelphia.
One block away from the Chester River and two blocks away from Downtown Chestertown, this home offers an updated kitchen with two wall ovens, Avanza countertops, ceramic tile floor with a brick fireplace and skylight. The large addition on the back has 8 sliding glass doors with a French door and brick step entrance into the kitchen. All windows have been updated and boast interior blinds for ease & to keep dust to a minimum. The crawl space has lighting and is completely encapsulated. A black metal fence surrounds the back yard with gate and a white vinyl privacy fence is located on the street side allowing the extensive landscaping and brick patio to be completely closed in by fencing. This all brick home in this highly coveted area is waiting for you!
Bring your plans & start building! The footprint is solid, the water & sewer lines are BRAND NEW, the electric supply and breaker box are BRAND NEW, and the lot is HUGE with tons of potential! All within walking distance to everything Downtown Chestertown has to offer... shops, restaurants, parks & the new marina. The backyard abuts the Rail-to-Trail pathway, allowing for easy access to the Chester River waterfront, Washington College & beyond - up to the shopping centers. Easy to see, come visit this great opportunity soon! *The fine print: plans would have to be approved. Property is located within the Historic District.
Welcome to this charming Cape Cod in the community of Chesapeake Landing. The 2/3 Bedroom 2 bath cottage is nestled in the water oriented community with deeded access to Worton Creek. Bright airy open floor plan with cathedral ceiling, enclosed loft room and wrap around deck. Worton creek is but a few hundred foot walk from the front door. Home is nestled in a peaceful wooded section of Worton Creek and is not in the flood plain.
This offering of one & 1/4 waterfront acres at the end of a cul de sac sits in a private, park-like setting on Worton Creek. The improved lot is fully bulkheaded with a dock. The well maintained three bedroom, two bath ranch with a waterside three season room has had periodic upgrades during its current ownership
Welcome to 'Knot Now Boat House', which has been a very tastefully remodeled home located on Fairlee Creek. This can be a full time residence or your Holiday retreat or week-end get away. Fully updated kitchen with new counter tops, cabinets, and stainless appliances, Wonderful color choices with paint,decorating and flooring. New HVAC system and tankless water heater. Has own private dock with power lift and jet ski ramps. Plenty of room for all your water toys. Detached garage with extra storage area. A must see if your seeking waterfront property with your own private dock.
Hilltop Farm C. 1810 in historic Chestertown includes 113 acres with waterfront on Langford Creek off the Chester River. Property includes large 8 feet deep fresh water pond and impoundment.Perc test done in 2019 for new construction 3500 +sf on the waterfront portion of the farm to accommodate a new waterfront residence with privacy. Many options with the property operating as a residence, farm or combination. Great relationship with local farmer regarding crops and maintenance. This is a rare opportunity to own a piece of Eastern Shore history and build your dream home surrounded by wildlife on the shores of Langford Creek.
Fabulous opportunity for multiple uses with the property. House can be a residence or rent out with a couple of apartments or office space. Oversized Garage is bigger than the house at 1760 square feet! Have a shop or keep cars or boats with all this space! Zoned suburban commercial. House has newly refinished wood floors and multipurpose floor plan. NIce private yard and plenty of off street parking.
Cute rancher located a few miles outside of Chestertown. Great living space. Kitchen has all of the major appliances. Laundry is located in the bath for easy access. Great backyard that overlooks farm fields. There is a one car detached garage. Currently used as a rental and has received a lead free certification.
Welcome to Tolchester Estates. This 2 bedroom 2 bath home would be perfect for a summer retreat or to live at year around offering stunning views of the Chesapeake Bay from your kitchen, dining room, and rear deck! This home is situated on nearly a half an acre with a 2 car detached garage. The property also features a well house w/ water treatment system and basement for additional storage and a gazebo to relax outdoors. Off the master bedroom there is a wonderful 8x15 sun room perfect for relaxing or additional space. The partially finished basement with walk out egress and a full bathroom offers endless possibilities. Put this home on your list to tour, you will not be disappointed.
Wonderful Water Street Condo with elevated views, a private balcony, and a boat slip to enjoy the Chester River. Large eat-in kitchen, beautifully renovated with stainless steel appliances, farmhouse sink and custom cabinets. The property also offers an open living room with gas fireplace and views of Chestertown's Historic District, in addition to a Master bedroom, two full bathrooms, and a second bedroom/office space. Perfectly situated to enjoy all the Chester River AND Chestertown's Historic District has to offer!
Opportunity is knocking!! This beautiful home is located in Heather Heights conveniently situated between The Chester River Yacht and Country Club and Historic Chestertown. The home is turn key and well maintained with spacious rooms, wood floors, corian counters, large florida room overlooking the back yard, with attached garage. There are currently 4 bedrooms with the option to take the smallest bedroom and make it an office like the current owners have. Call to schedule your showing!!
Big Price Reduction! Here's your private waterfront getaway or retirement home! Peaceful views of the water and yard. Fish and kyack from your backyard or launch your motorboat at the community boat launch 200 feet away. Home in good condition has large rooms with lots of windows bringing in all the views. Open floor plan with wood burning fireplace in Living Room. Enjoy the deck under the retractable awning or relax in the large screened-in porch. Large garage, perfect for your boat, car collection or work shop. The upstairs has a large finished Family Room and Bedroom. This property has a lot of potential with 1.75 waterfront acres and a short walk to the boat launch and community area. Easy to see!
Welcome to this prime Historic District location in charming Chestertown! This home features Victorian style, original wide plank hardwood floors, many of the rooms feature chair rail, and cornices, with high ceilings. Two non-working slate fire places. Side entrance to patio and rear entrance to large level yard and one car garage and two car parking area.
Goose Landing is a 3.17 acre 4 bedroom 2.5 bathroom secluded waterfront home nestled on Fairlee Creek that boasts 350 feet of waterfront with panoramic views from almost every room, a 100 foot dock with swim platform. Fairlee Creek is fresh water year round and has some of the best swimming, water skiing, kayaking and fishing on the Chesapeake. The entrance to the Bay, as well as Great Oak Landing, are only a five minute boat ride away. The Public boat launch is 1/4 mile away. Take advantage of historic Chestertown and Rock Hall for shopping and dining as they are both only 9 miles away. Enjoy entertaining with a large great room, fireplace, several outside deck areas, screened in porch, patio, and plenty of yard. Fun time in the large family room/ Game Room and fireplace for cozy nights. Let everyone help and cook in this Kitchen! It's perfect for entertaining with large Breakfast bar overlooking the Great Room. First-floor master Bedroom suite. Take the spiral staircase to the 2nd floor with 3 bedrooms and another full bathroom. Freshly painted home and Deck. A separate workroom with electric and covered storage site can be for a footprint to build another structure. Peace, nature, beautiful water and a great home at a terrific price!
You'll simply fall in love with this charming Cape Cod. Located in sought after Coventry Farms and minutes from historic downtown Chestertown. This home has been meticulously maintained; fresh paint, new flooring, countertops, and more! 4 spacious bedrooms, 2 bath, living room, kitchen/dining combo opening to the large deck for easy summertime entertaining! Come see everything this delightful hom and Chestertown has to offer! There are no HOA or Front Foot Fees.