The median home value in Chestertown, MD is $313,725.
the county median home value of $178,000.
The national median home value is $277,796.
The average price of homes sold in Chestertown, MD is $313,725.
Approximately 44% of Chestertown homes are owned,
compared to 42% rented, while
14% are vacant.
Chestertown real estate listings include condos, townhomes, and single family homes for sale.
Commercial properties are also available.
If you like to see a property, contact Chestertown real estate agent to arrange a tour
today! Learn more about Chestertown Real Estate.
This custom built home has TONS OF POTENTIAL. Currently 3 finished bedrooms and 2 bathrooms, with rough-in for 3 full bathrooms and a 4th bedroom. Reclaimed hardwood floors, upgraded trim, custom kitchen cabinets, built-ins and mill work. Wooden siding and updated BAT system septic and well. Situated in a beautiful wooded setting, with stone fireplace as well as a brick chimney, kennel run, basement, wide wrap around porch, circular driveway, a place for peaceful living. Perfect opportunity for an investor or handy home owner. CASH OR CONVENTIONAL ONLY. NO FHA, VA or USDA.
Adorable fully remodeled 3 bedroom 1.5 bath in water oriented community. All new everything from the siding to the roof, kitchen, appliances, floors, HVAC, New Well. A fully encapsulated crawl space. Large lot with sizeable outdoor building. Think Big Fiber Optic Internet available. Located just 2 blocks away from the Chesapeake Bay and just 1 mile from Tolchester Marina and The Shanty beach bar and restaurant.
Great quiet Neighborhood within town limits. Conveniences of town water and sewer and another plus with trash and brush pick up weekly. This is a solid 3 bedroom, 1 bath rancher with a traditional layout. Living room , dining area and over sized family room, that runs the length of the back of the house. Only one family has lived in this house thru the years. It is ready for a new owner to add their ideas and a fresh look. Gorgeous hard wood floors were found under the carpet. The wood work in the dining area is as shiny in person as it shows in pictures. Full attic with plywood down for extra storage. Back yard is fenced in . This house is move in ready and you could do some updating along the way to make it your new home.
This timeless home built in 1782 is unique to Chestertown due to its vast lot size of just under a half acre. It is known as the historic Bolton-Anderson House with many of it's original features. The two stories have endless potential to become anything you would want. About half of the walls are open and ready for electric. This saves money and time. The third floor can be easily turned into a charming loft with views overlooking the backyard. With just a block from the Chester River, restaurants, shopping and coffee places this is a rare opportunity for a buyer. Home is "AS IS".
Looking for great location and bright, sunny space? This house has it! Located in Chestertown, close to historic district shops, restaurants, and waterfront amenities, as well as the hospital, Heron Point, and so much more! This house is in a beautiful quiet neighborhood. Tons of space, a brand-new deck, and a bright spacious addition which provides great living space! Breakfast room has a fireplace, and the family room has a gas fireplace. First floor has a powder room and dining room, plus two bonus rooms that can be a formal living room, huge home office or hobby space, or play area. The den has new carpet installed. Second level has a full bath and four bedrooms. Solid bones with a traditional floor plan. Back yard is spacious and flat, plenty of room for games, and fenced-in space for your furry friends. All appliances convey. Easy to show. Just waiting for you to make it yours. Come check out this listing while it lasts.
Quiet and peaceful Eastern Shore living. 4 Bedroom 2 Full baths. Wonderful price in this competitive market to get what you want.. Very open floor plan with upgraded kitchen including stainless steel appliances and granite countertops. Lot conveniently located to all the major routes, only minutes away from Downtown Chestertown and Centreville. A short easy commute to Middletown, Dover, Annapolis, DC, and the beaches. Located in QA County school district. Lot is being cleared, then construction will start. Still time to pick out a few items, if you hurry in! Specification sheet under documents.
Fabulously Renovated Brick Front Rancher! Don't Miss this 4 Bedroom 2 Full Bath Rancher located in the sought after Byford Development in downtown Chestertown! True 1 Level Living! Seller has outdone themselves with so many upgrades! Gorgeous New Bright White Kitchen with Custom Wolfe Soft Close Cabinets in Hanover White, Brazilian Luna Pearl Granite Counters and Whirlpool Smudge Resistant Stainless Steel Appliance Suite. Interior is Freshly Painted with a Neutral Palette, New LVP Flooring throughout main living areas with New Neutral Carpet in all 4 Bedrooms. 2 Full Bathrooms are Beautifully Remodeled. New Windows! New Central A/C, Furnace and Ductwork! New Water Heater! New Architectural Roof! New 12 x 12 Rear Deck, New Slider and more!
Multiple possibilities for this 6.5 acre property: Interested Call listing agent for aerial maps of lot. - Total interior renovation project of an 1883 structure. Roof/siding is @ 8 yrs. Unfinished attic has eaves creating 2-3 additional nooks or storage. - Potential subdivision of road frontage into 2-3 lots for development. - Possible subdivision/development of open, tree-framed meadow pending disposition of pond. - The Pond (2.5 acres) is in its 7th year of a ten year contract under the Conservation Reserve Enhancement Program (CREP), CP9 Shallow Water Areas for Wildlife. Owners contract is transferable if the land is sold or inherited and new owner agrees to terms, or owner will satisfy current contract. - Existing property is on public water/sewer. Determining number of water/sewer hookups available for development is responsibility of buyer. ================================================== IMPORTANT ACCESS INFORMATION To view the inside of the home, appointments MUST be scheduled and approved. Schedule thru the Showing Time link in BRIGHT listing. Avoid yellow taped areas. Lockbox and access is thru side door. TAKE CARE TO MAKE SURE THE DOOR IS LOCKED when you leave. It may take take some jiggling to confirm door is securely locked. Those interested in the land only are welcome to walk the grounds without an appointment with the following stipulations: By accessing the grounds you accept personal responsibility. Winter weather can be wet & sloppy. Park only in the driveway, keeping an eye out for mud. Back out of driveway -- DO NOT use "Y" or "U" turns Be aware of the terrain behind the house until you reach the meadow/pond. Wear boots! Agents, please provide feedback. Feasibility study is recommended to determine if you can develop the property as you would like.
Nearly new 3 bedroom 2 bath home in Chesapeake Landing just outside Chestertown. Country living close to town with private back yard and privacy fence. Owner purchased new in 2020 and has relocated for a career opportunity.
Investment incentives and opportunities abound with this completely renovated mixed use building in the heart of downtown Chestertown. Currently receiving an Enterprise Zone property tax credit and eligible for a Federal Historic Preservation Tax Credit. For additional photos see Commercial listing MDKE2000588 Unparalleled location for office space and downtown living in Chestertown. Top to bottom renovation, with no expense spared. Everything in the building is new with the exception of the windows, which were restored and like new. Total square footage of the 4 floors is approximately 3,600 sq feet. Commercial space offers 7 private offices, reception area, conference room, kitchenette, storage room and 3 half baths. Office space encompasses the first floor and finished basement. Historic restoration with original character and new infrastructure. Soundproofing between rooms and floors, monitored fire alarm system. Set up for CAT-5 wiring and wall-mounted video displays. The residential apartment is located on the 2nd and 3rd floors. High end finishes throughout. Refinished wood floors, a combination of new and old wood doors and beams encased in reclaimed wood give the apartment add to the apartment's warmth. The kitchen is compact, but with copious storage, granite counters, a Carrara marble backsplash, stainless steel appliances and a custom wood-trimed ceiling and. 4 bedrooms, 2.5 baths with a common living area on each floor, as well as a private balcony offering a prime view of downtown Chestertown. Apartment is subject to current lease (through July 2022), commercial space is currently unoccupied. Commercial space also available for rent, either the entire space or parts of the suite.
Are you looking for Acreage near the Water? APPROX 4.01 ACRES.... This little bungalow could be very nice with a little TLC. Near Fairlee Creek and Town / Tolchester /Rock Hall Areas... Close to all the action, YET, secluded and Cozy.. House will need to be updated some, but seller has done most of the work recently.. 4+/- acres, mostly wooded with a Stream . Check with the county on Subdividing or Adding on. The lot runs behind the house and down to Mt Pleasant Rd. See Plat Map in the Documents section. Zoned Village . The zoning info is in the documents folder. Would also make a Great Rental Property ...INCOME OPPORTUNITY!! Contact me today to schedule your tour or should you need more information.
One floor living in country setting. Low maintenance three bedroom two full bath rancher on large lot with wooded area containing 4 acres total.. 10 minutes to Rock Hall or Chestertown and under 2 hours to Baltimore and Philadelphia. Property backs to farmland. Public sewer and water.
This circa 2011, white brick house was built to celebrate the expansive views over the Chester River Yacht &Country Club golf course to the Chester River. There is an attractive patio at one end and a screened porch off the owner's suite. The landscaping around the circular driveway is lovely; the garage is set on an angle as to be unobtrusive from the road and the house entrance. Inside, all the rooms enjoy the views; the glassed in sun room being the most spectacular. Beautiful flooring, oversize crown molding, chair rails, accent & recessed lighting and painted paneling throughout. New A/C handler, Rinnai system with boosters (to reach around this 4,000+ sq. ft. house), foam insulation underground and up the walls, crawl space encapsulated, 3 temperature zones and audio wired surround sound. The kitchen and owner's suite are too great to try to describe, for instance, the marble came directly from Italy and no longer available. Laundry and "mud kitchen" are between the owner's suite and garage. Take a golf cart to the club, ride a bike into town or just sit and watch the tall ships go by.
NEW CONSTRUCTION TO START RARE FIND. 28 .86 ACRE HOME SITE WITH 18 ACRES USABLE. GREAT NEW FLOOR PLAN 4 BED 2,5 BATHS. NO MORE WORRIES ABOUT NOT ENOUGH LAND. YOU CAN RUN, JUMP JUST GO CRAZY ON THIS LOT. FLOOR PLAN ONE OF THE BUILDERS BETTER LAY OUTS. 4TH BEDROOM COULD MAKE NICE HOME OFFICE. BRING YOUR OWN PLAN IF THIS ONE DOES NOT FLOAT YOUR BOAT. LOT IS ALSO FOR SALE OUTRIGHT AT MLS# FOR LOT IS MDQA2001100
This remarkable property has so much to offer! Comfortable home with so many quality features! Beautiful concrete pool w/ hot tub and poolhouse w/ bathroom/changing area, detached 26x38 heated garage/shop/office, great location in the sought after Quaker Neck area, near Chestertown, yet not isolated. 2+ acre partially wooded lot overlooking unspoiled farmland. Wood floors, 2nd floor laundry, sunroom, custom moldings, and much more! New Roof-2019 New Septic-2021 New HVAC-2021 This house has so many upgrades that you'll need to see for yourself.
Looking for country living with public utilities? This home has both!! Located 10 mins from Chestertown and Rock Hall on the outskirts of the village of Fairlee, this home is roomy inside and out. Offers just over 2 acres of land available for gardening, play, expansion, storage or just that extra breathing room. Only a short distance to Fairlee landing so bring the boat or water toys with you. Inside you will find many updates that include new paint, flooring, kitchen cabinets, granite countertops, updated bathrooms and even a media room or first floor bedroom with a one of a kind ceiling. The attic space has also been finished into additional living space, great space for a playroom or make into an additional bedroom or two. From the square footage to the acreage, this is quiet the country charmer. Looking to add an outbuilding â¦.you have more than enough room here. Plus a home warranty through Cinch home warranty company.
Located just ten minutes from historic Chestertown this is your chance to own an amazing property, with panoramic views, perched above the coveted "Fairlee Creek"! Enjoy spectacular sunrises and sunsets from your private dock where deep water slips, 6'+/- at high tide, are just minutes from the Chesapeake Bay, yet well protected. The house was re-built approximately six years ago, with all plumbing and electric replaced and foam insulation was applied for quiet and comfort. The kitchen was designed with dual main sinks, high-speed ice-maker, quartz countertops and an over-sized island. Itâs perfect for group cooking and entertaining. The first floor has six-foot-tall windows in the living room and main suites, providing water views from nearly every room. There are two owner suites on the first floor in a split floor plan design. Hardwood floors can be found throughout first floor. The upstairs has skylights, a loft bedroom with separate heating and cooling, its own private bath plus a very large bonus room. Ceiling fans can be found throughout the house, including the screened porch. Dual hot water heaters located in the encapsulated and conditioned crawl space insure the availability of hot water when you need it. A public boat ramp is located just one property away for amazing convenience and exclusivity.
Exceptional brick Cape Cod on the Queen Anne County side of Chestertown. This beautiful home features a Florida room, den with built-in bookcases, open kitchen and wood floors throughout. Mature yard with beautiful gardens. Quiet dead end street with little traffic and a whole house gas generator for backup in emergencies.
This recently updated colonial cottage is just adorable... BRAND NEW ROOF (!!), crawl space cleaned with refreshed insulation & vapor barrier, front porch, kitchen cabinets with quiet-close hinges & appliances, flooring, built in bookcases, bathroom flooring, vanity & fixtures, a fresh coat of paint throughout, new back patio with shade sail, and refreshed landscaping. The opportunity for off street parking is available via the public access alley behind the property. Convenient to the College, Downtown, the Library, the waterfront, grocery stores, restaurants. Its exactly what you're looking for in a Chestertown home!
This lovely Victorian, with peeks of the Chester River, has been updated and remodeled while keeping many of the original features. These include stunning parquet floors, hardwood floors, bulls eye moldings, wainscoting, built-ins and more. The front parlor has a gas fireplace and there are pocket doors between the generous size dinning room, parlor and the hallway. The gourmet kitchen has granite counter tops, stainless appliances and loads of storage. The family room has a wet bar, built in bookcases and a gas fireplace. The staircase to the second floor is simply beautiful. The master bedroom is huge and boasts a lovely master bathroom and walk in closet. The 2nd bedroom faces the water and is bright and sunny. The 3rd bedroom could be an office and has access to the 2nd floor balcony. The 3rd floor with its angles and great views has been used as an apartment. It has a kitchen, bathroom and separate outside entrance along with an inside entrance. The property is nicely landscaped and includes a back yard shed and raised beds for a garden. This is a real Water Street gem!
"Widehall" is the most acclaimed historic downtown waterfront estate in Chestertown MD, since 1769. The many stewards of this magnificent residence, including two Maryland governors and two US Senators, have been ambassadors of hospitality for both town folk and national leaders. Each have protected and enhanced its authentic beauty ... from the original mahogany hanging staircase (c 1769) to geothermal heating and air (c 2013). Widehall is quite special to our town. The more formal main floor rooms provide the ideal setting for both parties and intimate gatherings. The flow between each of the rooms is perfect. Three of the six wood burning fireplaces add only a part of the warmth and ambiance of the main level of this residence. The chilled air or warm summer breeze is steps away on the first of two grand verandas overlooking the Chester River, thoughtfully added in 1911. Ascending the mahogany stairs to the second floor maintains the elegant feel of a grand home but immediately establishes a feeling of comfort and relaxation with a large family room. Surrounded by three bedrooms, each with their private baths, there are two doorways to the second of the very large waterfront verandas. A former servants wing provides for a bath, laundry room and windowed closet space. The top floor (number three) boasts three bedrooms, two baths and an additional laundry. Architects of a by-gone era creatively used dormer space for exquisite closet and storage space. Currently, each bedroom is named in honor of an acclaimed figure with close connections to Chestertown and the Eastern Shore. Your journey is not quite finished. A gracious staircase, discreetly hidden behind a wainscoted door, brings you to the unmatched "Widow's Walk" or rooftop deck with the most spectacular views of the Chester River and Chestertown. In many cities, a visit to this rooftop would be worth the price of a hefty admission. Our beautiful town and its people want to welcome you to continue the history and stories of "Widehall". Prospective buyers should be informed of the vital socio-economic trend this small town of America is experiencing and that of its acclaimed Arts & Entertainment District. Yes, our weekly Farmer's Market is "gossip central" and awesome for river and farm fresh provisions .... but it is the community that makes us a great place to to live. From monthly First Friday evenings for gallery and shop visits to a variety of annual festivals that include Downrigging weekend, Legacy Day, the Chestertown Tea Party reenactment, Dickens of a Christmas, and more add to the vibrancy of our town with Widehall enjoying the best viewing action. The convenience of a deep water dock and great lawn combined with short-walks to morning coffee and fresh pastries, evening cocktails and fine dining is unparalleled on the Eastern Shore.
You will appreciate peaceful living in this waterfront community on the Chester River just minutes from historic Chestertown.. A light-filled and spacious open floor plan is wonderful for enjoying the elegant interior amenities. You will also want to sun bathe or swim at the lovely pool, stroll the shell walking paths throughout the community and along the shoreline, go kayaking from the community dock, or just sit back and relax while enjoying the Eastern Shore lifestyle.
Very spacious split level home sited on a corner lot in Foxley Manor offers open dining/family room pleasure with a galley kitchen. The family room accesses to a patio in the side yard offering privacy with the border of trees. The home offers large windows for natural lighting and views. There is an additional family room that is quite large offering exterior access to the rear yard. This home is located within the town limits of Historic Chestertown with great convenience to shopping, the library and restaurants.
Lauretum, an 1881 country house built in the grand manner, defines a period of American history when architecture was at it more picturesque and exuberant. An exemplar of the Queen Anne style, Lauretum, Latin for "laurel grove". This unusual landmark building was designed by the renowned architect, Edmund George Lind, commissioned by the prominent Vickers family, is rich in 19th c. history. An accomplished builder of the time, R.K. Pippin was the local contractor. Fine Pippin buildings are scattered throughout Chestertown emphasizing his importance as a builder. Approached by a gravel driveway that winds rising from the County road. Other aspects of Lauretum indicate the tasteful and selective influence of a master architect. Details include pierced fretwork, Oriole window, granite sills, elaborately paned window lights, Jib-way doors that allow the interior to open to the extensive open porches. The extremely high ceilings, room transoms and the many windows speak to the importance to the late Victorian penchant for cooling rooms and fresh air in designs of that period. Lauretum has been a residence, a Bed & Breakfast and currently the cooperate offices of a national firm. The construction is stucco over solid thick brick walls. The current owners relocated the kitchen while bringing the kitchen into the very modern era. It features fine architectural details, fireplace and high-end appliances. Please call for an extensive brochure on the many details of this fine property located within Chestertown on six acres high on a prominent hill. A National Register property. Lauretum is site on the Civil Trail. Because of its size, location and architectural prominence one can envision Lauretum is so many ways. A tour will bring those used to light. Lauretum, an 1881 country house built in the grand manner, defines a period of American history when architecture was at it more picturesque and exuberant. An exemplar of the Queen Anne style, Lauretum, Latin for "laurel grove". This unusual landmark building was designed by the renowned architect, Edmund George Lind, commissioned by the prominent Vickers family is rich in 19th c. history. An accomplished builder of the time, R.K. Pippin was the local contractor. Fine Pippin buildings are scattered throughout Chestertown emphasizing his importance as a builder. Approached by a gravel driveway that winds rising from the County road. Other aspects of Lauretum indicate the tasteful and selective influence of a master architect. Details include pierced fretwork, Oriole window, granite sills, elaborately paned window lights, Jib-way doors that allow the interior to open to the extensive open porches. The extremely high ceilings, room transoms and the many windows speak to the importance to the late Victorian penchant for cooling rooms and fresh air in designs of that period. Lauretum has been a residence, a Bed & Breakfast and currently the cooperate offices of a national firm. The construction is stucco over solid thick brick walls. The current owners relocated the kitchen while bringing the kitchen into the very modern era. It features fine architectural details, fireplace and high-end appliances. Please call for an extensive brochure on the many details of this fine property located within Chestertown on six acres high on a prominent hill. A National Register property. Because of Lauretum's proximity to a well-known and admired Historic Town (home of Washington College - tenth oldest in America) one can envision the many ways Lauretum could be used including a lovely residence.