The median home value in Chestertown,
MD is $291,000.
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 $291,000.
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
Commercial properties are also available.
If you like to see a property, contact Chestertown real estate agent to arrange a tour
Learn more about living in Chestertown.
Don't miss this special location on Queen Street with 3 off street parking spaces and a rear bonus room that could easily be converted to a first floor master suite! A major renovation in 2015 brought modern infrastructure underlying the historic details AND added living space including a new kitchen with a roomy screened-in side porch, and a vaulted bonus room with cork flooring which is perfectly situated to suit a variety of needs. This flexible space was built with a potential master suite in mind and is currently being used as a family room and formal dining area. A full view of the fenced courtyard garden expands the feel of the bonus room while preserving privacy. It is conveniently adjacent to a full bath and laundry, making it nicely situated for conversion for one floor living, or for use as a family room, game room, beautiful office, studio, huge formal dining room, or anything else to suit your situation. This house is built to adapt and flex with your needs! The eat-in kitchen is truly in the heart of this home. Enjoy cozy cork flooring and a matching suite of stainless GE appliances. The kitchen has three doorways: One to the screened porch & the outdoors, one to the formal living room in front, and one to the laundry, bath, and bonus room to the rear. You may find that entering from the screened porch from your private parking is most convenient, while the front porch entry may be your choice after walking around town. The front porch is the place to socialize with neighbors and to enjoy the beautiful street-side gardens for which historic Queen Street is known. From the front door, invite your guests into the formal entry hall featuring a coat closet, and stairs to the second floor which leads the eye to a peek of the upstairs hall overlook. The living room is to the left in the front of the home with a gas fireplace and a handy office nook tucked under the stair. The second floor leads to two private bedroom suites both with ensuite full baths! The third floor does double duty in its current use as an artist's studio with a sink on the left and also the third bedroom with a twin bed to the right of the stairs. Right in the beating heart of historic Chestertown, this home is within a block of fine dining, an artisan bread bakery/coffee shop, a clay studio, art galleries, the Garfield Center for performing arts, the County Court house and just about two to three blocks to an ice cream store and Luncheonette, the Saturday Farmer's Market at Fountain Park, the Chester River front, the new playground at Wilmer Park, the rail- trail, post office, Cross Street shopping, Natural Food Store, and more! Home to Washington College and many festivals, Chestertown also has a brand new YMCA and is within one and a half to two hours of Baltimore, Washington, and Philadelphia airports!
Simply charming cottage in the water privileged community of Chester Harbor. The interior has been freshly painted and there are new floors through out. New built in microwave, new dryer and bathroom vanity are just a few of the upgrades. There are two bedrooms on the first floor, a third bedroom on the second floor and a home office on the second floor which could be a fourth bedroom. The yard is nicely landscaped with mature trees and new fence. It is move in ready and just minutes from Chestertown!
In c1750 this iconic property was known as Bedingfield Hands House and has enjoyed a storied life with many prominent Chestertown residents. Today, this well-maintained historic gem with enchanting curb appeal has hosted many an event for some of the most beloved non-profit organizations that give our town a very special sense of community. Before even entering the front door, visitors are welcomed by its' large, brick-pathed and picketed fence terraces and irrigated garden beds. One side path leads to a mudroom entrance, another side path guides you to a nicely sized private brick patio and screened porch. The foyer includes a full-size bath and hanging closet. To the right is an intimate library (possible 4th bedroom) with built-in bookshelves. To the left, the large living room with fireplace (currently gas) leads to a formal dining room with another fireplace and corner cabinet. Further on is a most inviting country island kitchen with hand-painted wood cabinets, stainless appliances (new in 2016), breakfast area and powder room. Access to the garage is through an ample mudroom/laundry room. The breakfast room door gives way to the rear patio and screened porch. Upstairs hosts the primary bedroom with ensuite bath with unique ceramic floor tiles. Two additional bedrooms share an end-of-hall bath. The overhead attic with pull-down steps is insulated and suitable for storage. The crawlspace below was also recently insulated along with a complete caulking of its' wood siding as part of an energy efficiency initiative. Please notice that this Realtor waited until the very end of remarks to use the word "charming" ... but it is a must to state.
Stunning, well cared for home in Coventry Farms II is the envy of many with it's beautiful landscaping and stone accent, an incredible value. Looking for Turn Key? Seller willing to negotiate with buyer on the furniture too. As you enter the front door, you are embraced by the warmth and comfort this home has to offer. You are greeted with remarkable wood flooring that flows throughout most of the home. To the left of the foyer, you find a formal living/den/office space. To the right a formal dining room that can accommodate a formal dining set or casual set with it neutral color and detailed crown molding. You will find just off the foyer the half bath which is conveniently located on the main floor for your guests. As continue through the foyer to the back of the main floor, the home opens up to a grand kitchen to the right and family room to the left. You will fall in love with the eye catching stone wood burning fireplace located in the family room. The kitchen is superb with it's granite countertops, wood cabinets, stainless appliances and large island with seating. If that isn't enough to knock your socks off, there's a bump out off the kitchen that is currently used as dinning space but could be converted to addition living space or sunroom...let your style decide. The second floor offers 4 bedrooms and two full baths. The primary bedroom located to the left of the stairs includes plenty of closet space as well as a large private bath. Soak your troubles away in the soaking tub. Not a tub person? No worries, you will find there's a separate shower along with double vanity, what's not to love?? Three nice sized guest bedrooms and hall bath complete the second floor. But wait, there's a whole other level! Not your typical basement, but another complete living area! The additional bedroom, full bath and living space with access to the backyard, is perfect for the multigenerational living situation. No matter if you decide to move in the in laws or rent to a tenant, you will find the lower level has everything you need including the unfinished space that houses the laundry area. Use this space for storage or finish it off. Either way, you can't go wrong. Let's head outside from the lower level to the the backyard, where you will be in awe of the entertaining space that awaits you. Complete with patio, BBQ space, Pegula and all enclosed for privacy, you will enjoy many hours of sun and fun. Everything was considered when designing the backyard space. No worry about storing the boat or camper, this yard includes a parking area for the toys and within the enclosed area so to comply with the community rules. Location, Location, Location! This home has it...large corner lot and adjacent to the community space, it's the perfect place to take a stroll or walk those beloved four legged family members. The perfect combination of town living with a country feel. Only minutes to downtown Historical Chestertown and all it offers. Near by walking trails, waterways and scenic views...what more do you need. No mater if you work remote, commute to the office or travel for work, this home is within driving distance to BWI and Philly airport, Wilmington De, tax free shops in Delaware, Easton, Annapolis, DC , and Baltimore. Don't miss your opportunity to snatch up this incredible value. Schedule a tour today!
Buying a new home in historic Chestertown continues to be the best option on the Eastern Shore for those looking to retire or start a new family surrounded by the tranquility of upper shore living. This is a unique opportunity to buy an affordable, yet brand new home located centrally in town a short walking distance to local stores, restaurants and the new YMCA. Your new home is a short drive from Washington College and Chestertown's historic waterfront district. This NEW CONSTRUCTION single story 3 BR duplex style townhome is complete and ready to move-in with no HOA fees or regulations. This end unit home has a private front, back and side yard with off street driveway. Inside, a modern open concept floor plan, upgraded stainless steel appliances, granite countertops and bright white cabinetry are a welcome invitation to comfortable living. There is a separate laundry room and multiple linen and storage closets to keep your living area organized. All living areas have easy to clean and maintain durable vinyl plank flooring. This single story townhome has 3 generous bedrooms and 2 full bathrooms including a master bath. Both bathrooms have matching granite countertops in modern design which coordinate with the main living area. This private end lot offers a back porch with oversized private storage closet.
Here's a sweet spot on historic Queen Street... not only a great location within a block or two of everything Chestertown, but also a sweet spot to call home with front and rear porches, a garden patio, and cozy sun-filled living spaces that say "stay awhile!" After a major rehab in 2006, this beauty has since been gently used on a part time basis and well maintained by a caring owner. Agents, please read additional agent info. It's entirely move-in ready!The owner has completed a pre-sale home inspection to share with potential buyers. From the front porch, enter onto original wood floors into the living room with a gas fireplace featuring a uniquely beautiful salvaged mantle that provides a focal point for the conversation area. The entire home is light and bright from numerous windows and wide side alleys that allow the sun in from all angles. The dining room features the original fireplace (non-working) which adds architectural interest and makes a great dry bar when entertaining. The kitchen in the rear of the home has a half bath next to the rear door, a laundry room with a window, a coat closet, a cooking island/breakfast bar, and room for a table. The ceiling over the table space is pre-wired for a pendant lamp or chandelier. Enjoy stainless appliances, granite countertops, ceramic tile flooring, a double sink with a window, and a dual fuel Jenn Air range with a downdraft exhaust fan, a gas cooktop, optional indoor grilling, and an electric oven: preferred for even baking! Upstairs, you'll find three bedrooms and two full baths. The front bath has a stall shower. The rear bath has a massive cast iron claw-foot soaking tub to stretch out in and features optional extra heat from a ceiling fixture to make it luxuriantly toasty while soaking in the tub! Both full baths are generously sized with a window and ceramic tile. The hall to the front bedroom has a door to enclose the nearest bath and make it en-suite-or-not, giving you flexibility to adapt for guests or family as you like. The rear bedroom has a vaulted ceiling, a window seat, a view of the garden, and is adjacent to the hall bath with the clawfoot tub. The third bedroom, currently used as a music room, has a window and a cute bookcase style closet. It would make a nice office, a generous walk-in closet, or hold a single bed. The third floor is unfinished attic space providing generous storage which is easily accessible via a staircase behind a door in the front bedroom. The attic is floored and has old plaster walls, two windows and has access through a wall panel to an additional lighted attic area that houses the AC ductwork. This home has street parking and the added convenience of a shared off-street parking space to the left of the front porch in the deed! Walk to the Saturday Farmer's Market, restaurants, shops, the Chester River waterfront, marina, natural foods, neighborhood groceries & convenience stores, bread shops, coffee shops, pizza, ice cream, numerous parks including a brand new playground at Wilmer Park, and even some professional services, all easily walkable from this fabulous historic district location, N Queen Street!
This home has undergone a tasteful renovation including new plumbing, wiring, framing, mechanicals, and roof. The home offers a terrific floor plan with decorative touches which include built in book shelves and cabinetry, original and reclaimed wood floors, exposed brick and wainscoting. The first floor features a full bathroom and doorway leading to the rear brick patio. Upstairs features two bedrooms, a full renovated bathroom, ample storage and access to a large unfinished attic. The location makes for an easy walk to Downtown, waterfront, shops and restaurants. The home is currently rented so please allow for 24 hour notice prior to showing.
Being sold to settle an estate, LIST PRICE STARTING PRICE, Deposit required to Bid $25,000, buyers premium applies, see full terms and conditions at the website, Contents of the house to follow real estate auction including mowers, tools, and boat. Pre-Auction offers are accepted. Property close to Round Top Park
This beautiful brick-front colonial home features a multitude of upgrades, three finished levels, and is located in a quiet and friendly neighborhood. Stunning laminate Pergo flooring meets you at the front door and carries throughout the open and airy floor plan. Lovely formal living room is situated directly off the foyer and is a great place to welcome guests in. Main level study boasts glass pain French doors and welcomes in delicate daylight. Spacious family room seamlessly flows into the sunbathed dining room that gives access to the rear sun deck. Gorgeously updated kitchen boasts stainless steel appliances, recently painted cabinets, large double sink, and moveable butcher block island with seating. Generous primary ownerâs suite hosts an expansive walk-in closet. Lavish primary en-suite bath is complete with double sink vanity, corner soaking tub, and large standing shower. Three additional bedrooms and a full bath are also present on the upper level. Lower level has been completely finished including an elegant full bath, and two forms of egress. This level creates the perfect theater room, billiards area, and exercise room. Spacious rear yard is newly fenced with vinyl privacy fencing and is a great place to soak up the summer sun. Rear patio holds a high efficiency, relaxing hot tub shaded by a canopy. Additional upgrades include fresh paint, updated light fixtures, new washer, landscaping, and a recent roof tune-up. Enjoy the peaceful and quiet views of Chestertown where you are centrally located to many popular surrounding areas. Experience the Chestertown farmerâs market and being 6 miles from Rock Hall where you can enjoy the surrounding water. Take advantage of this opportunity to own a beautiful home tastefully updated in a quiet and friendly neighborhood.
Located in a small cul-de-sac, this terrific home offers so much. The primary bedroom on the first floor has an attached bath, there are three closets for those of us who love to shop! Speaking of shopping, you are a quick five minutes away from our wonderful shops and restaurants on High Street. A roomy living room looks out onto the front lawn, and is cozied up with a gas fireplace. Exiting the living room, next is the dining area, which is also open to the den and a door into the kitchen. The den is a newish addition to this home, and overlooks a private back yard, with a beautiful deck. The yard is fully inclosed, so no worries with your furry friends. The kitchen has a breakfast area with the laundry room just off of the kitchen area. There is a large 2 car garage with more than ample storage. You will love the convenient location along with the beautiful setting! Come see this treasure!
Water, water everywhere! This incredibly unique property is situated on a sheltered deep-water creek offering a westerly, southwesterly exposure with uncompromised sunsets. Fairlee Creek offers one of the most convenient boating accesses on the upper Chesapeake Bay. This 1.9 acre property comes improved with 2 homes, a deep water dock with 5-6' depth, an outdoor barbeque patio overlooking the creek, and 575+/- feet of secure shoreline. One of the two homes on this spectacular property is conte-levered above the water offering the feeling of being on a yacht with panoramic views from every room. The second home is a three bedroom, comfortable, one floor rambler with lovely screen porch overlooking the creek. The location of this property is notable in that it is centrally located in unspoiled Kent County and convenient to both historic Chestertown and the bayfront town of Rock Hall. Great Oak Marina and Resort is a short stroll of golf cart ride away where the residents of Great Oak Estates may share in the use of the establishment's facilities including the pool, restaurant, beach, and 9-hole golf course. Great Oak Estates is a fun-filled neighborhood where the residents interact well together and the spirits are active in the summertime and peaceful in the wintertime!
Great opportunity to buy in Chester Harbor. Perfect for a first-time homebuyer , investor or someone wanting a second wanting to take advantage of this water privileged community . Hardwood floors and more! Property offers 3 bedrooms and 1 full bath, Nicely landscaped with mature trees and nice landscape. Come and take a look, easy to show, being sold as-is.
This charming family home located in the Village of Fairlee requires rehab work however when entering the property one will agree that indeed it has alot of character with great potential. There is a large two car garage with a workshop. The parcel is 1.5 acres with a large part of it being fenced in the rear. Selling as is.
Look no further, 1,820 square foot home on the most desired, Queen Street, to your dream, Rose Cottage. Rock on the front porch or eat in the enclosed back porch with large picture windows looking out onto the brick patio into the pond, and through the attached arbor to the secret garden, all fenced in. This place is a RARE FIND! Inside, a welcoming fireplace in the living room, built-in hutches/cupboards, shelves over the doorways, crystal chandelier from Vienna, professional library off the dining room, large country kitchen, propane range, huge closets throughout, plus a large cedar closet - so much space, lots of lights. The third bedroom boasts exposed beams, with cottage windows with view into the trees, exposed chimney brick in 2 of the rooms. Romantic, come and see...
Beautiful, elevated views of Fairlee Creek from this enjoyable home, situated out of the flood zone, in a quiet country setting. The private dock has deeper-water, plus there is a very convenient public boat ramp very close to the property. From this protected location, you can boat out to the Chesapeake Bay in just minutes. Gourmet kitchen with an over-sized quartz island and countertops, open to both the dining and living area, as well as the water views, perfect for entertaining. There are two bedroom suites on the first floor, as well as a third bedroom and bonus room on the second. Hardwood floors throughout. Brick-floored porch faces the water to enjoy the view. A delightful screened porch on the other side of the house will become another favorite spot. Just minutes to downtown Rock Hall and Chestertown. Under two hours from Philadelphia, South Jersey, DE or DC;. Don't miss this comfortable waterfront property, perfect as a family retreat or retirement destination.
This historically designated home, situated on High Street with a refreshing gaze of the Chester River as you enter, receives many a pause by passers-by as they meander the brick sidewalks of downtown Chestertown. The 1790 residence was completely renovated and expanded in 2004 with an eye for both formal entertainment and comfortable living. The gracious foyer with front staircase and ample coat closet leads to a large parlor with original crown moldings and a fireplace. The generously sized dining room has an adjacent wet bar, powder room and storage closet. A rear staircase leads to the primary suite on the second floor. An open floorplan emerges beyond with large island kitchen, a second dining space and sun-soaked living room with built-in cabinets and bookshelves. A wall of paned windows and French doors overlook a beautiful garden with brick pathways and mature plantings. While this beautiful property is recorded as a four-bedroom house, it currently features the entire middle to rear second floor as a primary suite with office, graciously accessed by a back staircase. The south-facing bedroom, with large walk-in closet, has a pair of French-doors leading to a nicely sized roof with wood railings and copper-topped pilasters waiting for a deck and perhaps pergola. A marbled bath includes soaking tub, glass enclosed shower, pair of sinks and full-sized washer and dryer. The office (or 4th bedroom) completes the primary suite. The front staircase leads to a nicely proportioned bedroom with fireplace and ensuite bath. Finally, another paneled door sparks curiosity until it is opened and a solidly built staircase with landing is revealed. An enchanting bedroom with two built-in beds, gabled roof, walk-in closet and ensuite bath awaits. This floor makes a perfect hideaway. The basement is 2/3 concrete slab and 1/3 wood planked lighted crawl space offering plenty of storage. A hobby/workshop room has a laundry sink. All mechanicals are easily accessed and well labeled.
Price Improvement - listing price just reduced 10,000. Welcome to this well-maintained and appointed home located in the sought-after desirable Coventry Farms Community. This upgraded 4 bedrooms, 3.5 bath colonial home includes a partially finished basement with a new finished full bathroom. This area could be an additional family room, home office or home gym. The ideas are endless. The main floor features an open concept kitchen, eating, and family room area. There is an additional dining room or could be used as home office. The primary ensuite is located upstairs with an additional three bedrooms and an additional full bathroom. The walk out basement will lead you to an enclosed porch under the deck with lots of room for entertaining. You will enjoy coffee on your deck overlooking the open back yard. Lots of room for children to play. All this is offered just outside of Downtown Chestertown, convenient to restaurants and shopping, Marina's and boat ramps nearby.
Welcome to this Beautifully Remodeled 4 Bedroom 2 Full Bath Freshly Painted and Fabulous Brick Front Rancher located in the sought after Byford Development in Downtown Chestertown! The Seller has outdone themselves with so many updates! Enjoy True 1 Level Living! Gorgeous New Bright White Kitchen with Custom Wolfe Soft Close Cabinets in Hanover White, Brazilian Luna Pearl Granite Countertops, White Gloss Subway Tile Backsplash and a Whirlpool Smudge Resistant Stainless Steel Appliance Suite and portable island. The Interior is Freshly Painted with a soft Neutral Palette, New LVP Flooring installed throughout main living areas with New Neutral Carpet in 3 of 4 Bedrooms and Modern Lighting. The 2 Full Bathrooms are Tastefully Remodeled with Custom Vanity Cabinets. New Windows in Every Room! New Central A/C System, Furnace and Ductwork! New Hot Water Heater! New Architectural Roof! Front yard is nicely landscaped! New 12 x 12 Rear Deck perfect for entertaining, New Sliding Glass Door, New Gravel Driveway and more! Schedule your showing today!
Welcome to 311 Mayfair Drive in the sought after Coventry Farms community with NO HOA! This home is sitting on just over a half acre lot and the list of upgrades is amazing! With OVER 2700 sqft of true living space, this gorgeous rancher is ready for you! In the mornings, relax on the front porch and listen to the birds chatting away in the mature trees. Enjoy stress-free, low maintenance landscaping. As you enter the home, you will notice the gorgeous hardwood floors with fresh floor polish in 2022 and 9ft ceilings throughout the main living areas. To your left, you have a large living/sitting room and/or office that leads into a formal dining room and then into the kitchen. As you walk in from the foyer you enter the HUGE Great Room. This room offers large windows and a sliding glass door to bring in the natural light and leads out to the deck and spacious backyard with plenty of room to play and have fun! Off of the great room and formal dining room is the beautiful kitchen. It boasts newer stainless steel appliances and an abundance of cabinet and counter space. This kitchen is everything you are looking for to make your culinary masterpieces! Moving down the hall to the opposite side of the home, you have 3 large bedrooms with newer carpet and 2 full bathrooms. Each bedroom has great closet space and nice natural light. The ownerâs suite is large, has a walk in closet with a closet organizer, and a comfortably spaced bathroom. Back to the kitchen, you have an adjoining sunroom, with electric, for entertaining guests, have a crab feast, or simply to enjoy the fresh air from the numerous windows. You will want to spend many days and nights out here! The sunroom leads out to a TRULY OVERSIZED 2 car garage, 25x30, with 12 ft ceilings and lofts. Massive storage space/workshop! The roof was replaced in 2019 with a lifetime warranty! The 22-seer dual-stage hybrid-heat pump HVAC system and the Navian tankless hot water heater are 7 years young. The home has a whole house water filtration system PLUS reverse osmosis system that were installed in 2015 and regularly maintained. The BONUS, the massive attic can be used as storage OR can be finished to add another 1,000+ of living space. This home is one of a kind and you will not find another home like it in Coventry Farms. Only minutes to downtown Chestertown, restaurants, shopping and marinas. This is the one you want to call HOME!
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.
Come check out this Modern Split Level home just built and finished in Nov 2021. Still has time left on the builder 1 year warranty. This 3 bedroom 2.5 bath has tons of living & entertainment space, and a wonderful open layout. The Cathedral Ceilings, Hardwood floors, and spacious kitchen with Granite counters and Stainless appliances, many upgrades above and beyond builder grade to include shower doors, Tile in master, larger vanities, water softener, ceiling fans, bump out making for larger rooms and oversized two car garage, etc. Master Bedroom with attached bath and jetted tub. Huge lower level for extra living space or bedroom. All located in a peaceful setting. Call today for more info!
Water privileged community with the convenient offering of hopping in the boat and being out within minutes for water pleasure whether it be water sports, fishing or crabbing. This home is just minutes from Chestertown and Rock Hall for dining and events. Voluntary HOA. Open floor plan.
You will immediately feel at home in this beautiful, stylish Cap Cod perfectly sited on 1 acre tucked into nature. This home offers an open floor plan - living room, dining area and kitchen with SS appliances, 4 bedrooms (2 on main level) and 2 full baths....Additional highlights include large laundry/mudroom, sidewalk, new deck off back - perfect spot for relaxing/entertaining, oversized detached 2 car garage with 2nd floor storage space, ample parking and roof only 3 years old. This one is a winner!
One Level Living! Rancher for Sale in Washington Park Community 4 bedrooms (one being used as dining room currently) 1 1/2 Baths Nice LIving Room Separate Laundry Room New Windows 2016 - New Carpet in Living Room and Laminate in Kitchen and Laundry Room 2019