The median home value in Chestertown, MD is $395,000.
This is
higher than
the county median home value of $249,900.
The national median home value is $308,980.
The average price of homes sold in Chestertown, MD is $395,000.
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 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 2-bedroom, 1.5-bath bungalow offers a bright, open layout with updates throughout. The home features a sun-filled front room, an eat-in kitchen with new butcher block seating and updated appliances, and a fully renovated bathroom with new tile and a modern vanity. A rear utility room with laundry provides extra storage and access to a small backyard-perfect for gardening or relaxing outdoors. Located within walking distance to Downtown Chestertowns restaurants, shops, farmers market, and waterfront, this property is a great opportunity to enjoy convenient in-town living.
Welcome to this beautifully designed 1,980 sq ft home in Chester River Landing, offering modern comfort and timeless style. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the living space, with cozy gas fireplace, to the gourmet kitchen and dining area-perfect for entertaining. Upstairs, the primary suite features a spa-like bath, large walk-in closet, and access to the private balcony. Two additional bedrooms share a full bathroom. the upstairs is complemented by a convenient second-floor laundry. Catch a glimpse of the Chester River from the front porch or upper covered balcony, the perfect place to enjoy morning coffee or evening cocktails. Enjoy the waterfront lifestyle of the sought-after Chester River Landing community. Deep water boat slips are available for lease or purchase. The community amenities include docks, in-ground pool, grilling and outdoor dining area right on the water, large firepit, a beach to launch kayaks, canoes and paddle boards, beautifully landscaped paths along the water's edge and much more! This home combines the charm of the Eastern Shore with the convenience of nearby marinas, shopping, and dining. Located just outside of downtown Chestertown and very close to the Chester River Yacht & Country Club.
Welcome to this beautifully designed 2,092 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 3.5 baths. Inside, an open-concept main level connects the great room, gourmet kitchen, and dining area-perfect for entertaining. There's also a private study, which could be used as additional space for guests. Upstairs, the primary suite features a spa-like bath, large walk-in closet, and sliding doors to the second floor balcony. There are two additional bedrooms, each with their own full bathroom. the upstairs is complemented by a convenient second-floor laundry. This home is designed with future needs in mind, offering the option of a residential elevator for effortless access to all levels. Enjoy the waterfront lifestyle of the sought-after Chester River Landing community. Deep water boat slips are available for lease or purchase. The community amenities include docks, in-ground pool, grilling and outdoor dining area right on the water, large firepit, a beach to launch kayaks, canoes and paddle boards, beautifully landscaped paths along the water's edge and much more! This home combines the charm of the Eastern Shore with the convenience of nearby marinas, shopping, and dining. Located just outside of downtown Chestertown and very close to the Chester River Yacht & Country Club.
Welcome to this beautifully designed 2,231 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the great room, with gas fireplace ,to the gourmet kitchen and dining area-perfect for entertaining. Upstairs, the primary suite features a spa-like bath, walk-in closets, and doors to the private waterfront deck. Two additional bedrooms share a full bath. the upstairs is complemented by a convenient second-floor laundry. Enjoy broad water views and breathtaking sunrises over the Chester River. The covered porch and expansive windows create a seamless connection to the outdoors, enhancing the waterfront lifestyle of this sought-after community. Deep water boat slips are available for lease or purchase. The community amenities include docks, in-ground pool, grilling and outdoor dining area right on the water, large firepit, a beach to launch kayaks, canoes and paddle boards, beautifully landscaped paths along the water's edge and much more! Nestled in the sought-after Chester River Landing community, this home combines the charm of the Eastern Shore with the convenience of nearby marinas, shopping, and dining. Located just outside of downtown Chestertown and very close to the Chester River Yacht & Country Club.
Welcome to 304 Hadaway Dr. This classic home has been completely reimagined and is ready for it's next chapter. Entering the home you will immediately notice the beautifully refinished original hardwood floors. As you make your way down the hallway past the newly renovated hall bath with custom tile and designer fixtures, you will find 3 spacious bedrooms. The large family room transitions into a perfectly sized dining room and conveniently placed laundry center. The kitchen is absolutely stunning, with stainless Steele appliances, granite countertops, 42" cabinets and new hardwood floors. Moving into the large primary en suit bedroom, you will fall in love with the spa like bath with a large granite vanity, custom tiled stand up shower and tile floors. The home has a brand new 30 year architectural shingle roof, new windows, furnace, water heater, flush mount lights and the whole house has been painted on the interior and exterior with Sherwin Williams designer color collection. Enjoy the large and lush front and back yards, and large driveway. All within walking distance to Washington College and the beautiful and historic town of Chestertown.
PRICE REDUCTION! Motivated Sellers - BRING US AN OFFER! This house has appraised for over $500,000 = Instant Buyer equity! Sellers' loss is your gain! This stunning 4-bedroom, 2-full-bath home is just steps from Washington College and a short stroll to downtown Chestertown. This treasure is full of historic character blended with modern updates! Sellers have INVESTED $60,000 IN RECENT UPGRADES this year, including a brand NEW roof, new electric wiring throughout the entire house, privacy fencing, fresh interior paint, and crawl space moisture barrier. The first-floor features airy living, dining, and kitchen areas and a full bath. A bright screen porch with mahogany floor converts to an all-season room overlooking the lovely, fenced backyard, ideal for year-round enjoyment. Upstairs, youll find three generous bedrooms and another full bath, plus a third-floor lofted bedroom perfect for guests or a private retreat. Original heart-pine hardwood floors run throughout. All upgrades were intended to be enjoyed by current homeowners, but they are regretfully moving to be closer to a new job. With unbeatable proximity to the college and downtown, this home offers historic Chestertown living and incredible investment potential. Homes in this coveted neighborhood rarely hit the market-dont wait, this one will be gone before you know it!
Tremendously charming historic house, sensitively restored, a short distance from Great Oak Marina. Beautiful original 18th century pine floors, mantel pieces, six-panel doors and built-in cupboard. House was originally two small historic houses located in the village of Church Creek, Dorchester County, Maryland, moved to current location ca.1980. Private yard and garden. Chestertown and Rock Hall nearby. House has upgraded electric and Best Available Technology (BAT) septic system. Well water filtration system. First story bedroom and guest bedroom, additional bedrooms up. Modern kitchen with new Whirlpool brand stainless steel appliances, gas cookstove opening to family/entertaining area. Formal parlor with gas fireplace. Sunroom with skylights, tile floor, ceiling fan, overlooking garden. Most rooms have plantation shutters. Spacious closets. New recessed lights. If owner wants to join marina with pool and beach, it is believed that current fee is $100; additional dock fee if new owner has a boat and desires slip. $350/year road maintenance.
Welcome to this stunning 2023 built home - a move-in ready, three-story residence offering 5 bedrooms and 3.5 baths across 2,615 sq ft of thoughtfully designed space. The first floor features an open layout with a spacious family room, dining area, and bright, well-appointed kitchen. This level also includes a convenient first-floor laundry and a powder room. The kitchen is equipped with stainless appliances, a large corner pantry, and a generous peninsula. Upstairs, the owners suite offers a walk-in closet and an en-suite bath with a double vanity and walk-in shower. Three additional bedrooms share a full hall bath, also with a double vanity for added convenience. The third floor provides the fifth bedroom, another full bath, and a flexible space ideal for an office, playroom, media room or storage. Extras youll love: modern smart features, a fully fenced yard, and a backyard upgraded with pavers and a concrete patio, perfect for grilling, entertaining, or relaxing outdoors. Plenty of closets and storage space. With everything already complete, this home blends comfort, convenience, and style.
Kent County welcomes you with a move-in ready home thats full of updates! This 3-bedroom, 2-bath home sits on nearly a half-acre and is just minutes from downtown Chestertown. Enjoy peace of mind with a newer roof (approximately 5 years old), central heat and air, and a tankless water heater. The home features updated bathrooms, fresh interior paint, and a large laundry room with abundant shelving and space for storage. Outside, youll find a spacious yard, storage shed, and access to a wonderful community park with a pavilion and basketball courts. A great combination of comfort, convenience, and value in a desirable location! Kent County has 21 marinas, all within minutes of this location. Live, work and play here in Kent County!
Gobbler Hill, circa 1858 with an addition built in 1989, sits like a jewel atop one of the highest points in Kent County. Listed on the National Historic Registry, the transitional architecture is an excellent example of late Greek Revival to early Italianate. The property consists of four parcels totaling over 65 acres. Wildlife abounds on the fields of native prairie grasses, wild flowers, woods, approximately 20 tilled acres and a large pond. Impeccable attention was payed to maintaining the historic character of both the interior and exterior. From the Lincrusta wall covering, 19th century faux wood finishing, plaster medallions, white and sugar pine wood floors and crown molding on the 11 ft. ceilings to the monumental copper roof, the thoughtful restoration is stunning. The newer addition beautifully blends into the original section adding modern conveniences and natural light. The library boasts black walnut bookshelves constructed by a local craftsman. Well maintained grounds offer gardens, mature trees, a classic poured concrete in ground pool with inlaid tile and stunning views. This unique, lovingly restored piece of Kent County history is now looking for a new steward to guide it into its next chapter.
Gobbler Hill, circa 1858 with an addition built in 1989, sits like a jewel atop one of the highest points in Kent County. Listed on the National Historic Registry, the transitional architecture is an excellent example of late Greek Revival to early Italianate. The property consists of four parcels totaling over 65 acres. Wildlife abounds on the fields of native prairie grasses, wild flowers, woods, approximately 20 tilled acres and a large pond. Impeccable attention was payed to maintaining the historic character of both the interior and exterior. From the Lincrusta wall covering, 19th century faux wood finishing, plaster medallions, white and sugar pine wood floors and crown molding on the 11 ft. ceilings to the monumental copper roof, the thoughtful restoration is stunning. The newer addition beautifully blends into the original section adding modern conveniences and natural light. The library boasts black walnut bookshelves constructed by a local craftsman. Well maintained grounds offer gardens, mature trees, a classic poured concrete in ground pool with inlaid tile and stunning views. This unique, lovingly restored piece of Kent County history is now looking for a new steward to guide it into its next chapter.
Charming Move-In Ready Colonial in the Heart of Town This beautifully updated Colonial blends timeless character with modern comfort. Ideally located within walking distance of local restaurants, shops, and the scenic waterfront, it offers the perfect combination of charm and convenience. The exterior showcases classic Colonial appeal with vibrant shutters, fresh paint, new roof, gutters, doors, and Andersen double-hung tilting sash windows.The welcoming front porch overlooks manicured flower beds that enhance curb appeal, while the private backyard provides the perfect setting for weekend gatherings and cookouts or just outdoor relaxation. Inside, the home has been thoughtfully renovated from top to bottom. Recent updates include a Mitsubishi Mini-Split heating and cooling system,Rinnai propane instant hot water heater, and 200-amp electrical service with all-new wiring, fixtures, and recessed lighting throughout. The kitchen is a true showstopper that is completely transformed with new cabinetry, quartz countertops, a center island, stainless steel appliances, and a vented range hood. Refinished rustic hardwood floors run throughout the main level, seamlessly blending old world craftsmanship with modern design. A separate Laundry room features a new washer and dryer with Electric Hookups. Upstairs, youll find comfortable bedrooms with Shaw carpeting and pet-proof padding and a beautifully updated bathrooms featuring tiled walls and floors, new vanity, and modern fixtures. The dry basement offers a wide step entrance from Laundry Room with excellent storage space, a new 200-amp electric panel, vapor barrier, and plenty of room for a workshop or home gym or Man Cave. Enjoy the best of in-town living with everything you need just a short stroll away. Schedule your tour today and fall in love with this move-in ready gem
Two Story Colonial on 1.37+/- acre lot, rectangular 200 x 300 ft. Approximately 2,700 sq ft. of living area in house (estimate). 4 bedrooms, 2.5 Bathrooms. ½ basement with laundry room and fix-it shop/work bench with 2 crawl spaces. Attached two-car garage with abundant built-in shelving and free-standing cabinets for lots of storage space with garage door opener on each of 2 doors. Forced Hot Air, Fuel Oil Heating; Central Air Conditioning. Well water pump upgraded in 2016. New, top-of-the-line â??Meyersâ? well pump, with increased HP. Public sewer so no septic systems to deal with. Four upstairs Bedrooms. The MBR and BR2 are huge. MBR has slider door to lovely Sunroom/Sitting room. The MBR features wainscotting on all walls; crown molding; custom wide molding around all 3 doors and the closet with remote controlled ceiling fan with dimmable light. Large living room with stunning fireplace. Wide, extra-long mantle, matching storage cabinets on both sides of fireplace, large picture window and crown molding. Two full bathrooms with showers are upstairs, each with new, in 2024, quiet, yet powerful Panasonic exhaust fan and LED light. One Powder Room is downstairs. Bright and airy, extra-long dining room. Tray ceiling. dimmable LED ceiling lights on separate, inner and outer ring circuits for versatility. Ceiling centerline is pre-wired (includes 3-way switches) for one or more chandelier lights; Pass-through window to kitchen with fancy tempered glass shelf. Family room with dropped ceiling bar area. Bar sink, granite counters, gorgeous glass door cabinets, wood-burning stove, versatile lighting, and a slider door to a the main level sunroom. Modern, ample-sized kitchen with movable island. Nearly new, upscale glass cooktop/oven, dishwasher and microwave. Build-in refrigerator surrounded by cabinets. Double sink, disposal and PC workstation with shelving matching cabinet. Extraordinary lighting includes under and over cabinet lights plus a ceiling fan with fancy light globes and attractive light globes over sink. MAJOR ADDITION & REHAB done in 2013: Extended DR by 13 feet and added 2nd story sunroom/sitting room on top of DR extension Total rehab of 1st floor sunroom. Top quality, long lasting architectural roof shingle for entire house; new flashing and roof vent seals. Both sunrooms have attractive, casement-style windows for exceptional ventilation. Seven Ceiling fans with attractive lighting: MBR, BR2, BR3, 2nd story sunroom/sitting room, kitchen and 2 on the porch. All four Slider Doors (servicing the porch and the 2 sunrooms) have built-in blinds for privacy and versatile light and view control. Spacious screened porch with porch swing. Massive stone and paver patio area includes three 10x10 ft flat, paved areas for table & chairs. Large Campfire ring within the patio. Two lovely, Amish garden sheds in excellent condition and loaded with options: 12x16 ft. shed installed in 2010, and a 10x14 ft. shed installed in 2021. Huge 16x18 ft. Raised Deck using long-life Trex engineered planks; custom Pergola over one corner. Deep Shaded, 10 x 12 ft Outer Patio Area with Pergola. Mature Trees for great privacy and shade, especially around property perimeter. Three-level, split rail fence on rear and side yard property lines. (Left-side fence only is owned and maintained by the neighbor.) Extra-Wide Driveway. Paved Parking for 10 vehicles! Also suitable for camping trailer or boat.
Beautifully Updated Home in a Serene Setting! Welcome to this stunning home filled with thoughtful improvements and timeless charm. The spacious Florida room overlooks a private, beautifully landscaped backyard - your own personal oasis. This room offers unlimited views of the back yard, which was designed in collaboration with a professional landscaper, this garden is a delight in every season and a true haven for butterflies and hummingbirds. You will delight in an outdoor sitting area under a lovely shade tree. The main level features gleaming hardwood floor, a semi-open floor plan with a cozy fireplace perfect for cool evenings, and abundant natural light that creates a calming atmosphere throughout. The large primary suite offers comfort and convenience, and there is the option for a second bedroom on the main level. Current owners have opted to make that room a large office, and it features two closets. The kitchen is a dream - spacious enough for a large island and a generous breakfast area that easily fits a full-sized table. There is a mural border that shows scenes of historic Chestertown. Pantry and plenty of storage. Upstairs, youll find two large bedrooms and a full hall bath, ideal for guests or loved ones. Each bedroom offers walk-in storage - no attic ladders needed! Solar operated fans keep the attic spaces cool. Additional highlights include leased solar panels which have been paid out, a large garage with ample storage, additional storage shed with electric and water. , and a fantastic location just minutes from the Chester River and the Chester River Yacht and Country Club. Two zone for heating and cooling. Come see this charming home for yourself - its the perfect blend of beauty, comfort, and thoughtful design!
Live in the heart of Chestertowns Historic District-see your boat from your front porch! Beautifully rebuilt and expanded, this versatile home offers 3 1/2 baths and over 2,000 sq. ft. of finished living space. The rear addition features a sunroom/mudroom with separate entrance leading to a guest suite with walk-in closet and full bath. Upstairs, enjoy a second-story waterview deck-built strong enough to support a hot tub or additional living area (double 2x8 joists per owner). Andersen composite dual-pane windows with plantation shutters offer energy efficiency and easy operation. Ample storage includes two walk-in closets plus a walk-in attic. Located on desirable Water Street, youre just steps from the waterfront, Wilmer Park, shops, restaurants, bakeries, pubs, Farmers Market, arts district, and more. Cook and entertain in style with Heartland appliances and handcrafted cabinetry in the kitchen. 206 S. Water Street-a â??feels-like-newâ? historic home in Chestertowns most walkable location. Note The vacant lot next door is not part of this property. Separate owner.
Three bedroom one-floor living on a spacious lot in Chester Harbor! Over half an acre of nicely shaded yard space, and a short distance to the public beach on Mill Creek. 3 bedrooms and 1.5 bathrooms, open living and dining space, large sunroom/ porch with wood-burning stove, and an additional wood stove in the living room. Outside there's a small storage shed and a larger workshop/shed next to the asphalt driveway. The sunroom leads to a deck overlooking the large yard. Great community with water access. Quick ten minutes into Chestertown, and less than an hour to Middletown DE or Annapolis.
Are you looking for a property with an acre of land, detached garage with electric, public water/sewer, and NO HOA? Look no further! Welcome home to 8750 Georgetown Road, a well-maintained 3-bedroom, 2-bath property tucked away in the peaceful Chestertown countryside! This home offers the perfect blend of modern comfort and rural charm - an ideal retreat for anyone seeking space, privacy, and convenient one-level living. Step inside to discover a spacious open-concept layout, designed for both everyday living and entertaining. Outdoors, youll find a detached garage with electric service-perfect for a workshop, hobby space, or storage-as well as a large blacktop driveway offering ample parking for multiple vehicles, a boat, or an RV. The large yard offers plenty of space to garden, host gatherings, or simply relax and enjoy the open air. Conveniently located within minutes of historic downtown Chestertown, marinas, shopping, dining, this home delivers the best of Eastern Shore living-quiet country surroundings with easy access to Delaware and Pennsylvania.
Newly constructed three-bedroom townhome with all the desired attributes. Fantastic water views from the living level and bedrooms! Spacious open living space with warm hardwood floors and a gourmet kitchen. 5-burner induction range, ample cabinet space, and a large island for entertaining. The home is filled with natural light and boasts multiple balconies and a front porch for relaxing. On the second level you'll find two bedrooms and two bathrooms. There's extra room for an office nook. The third bedroom encompasses the entire third floor and has a great view of the Chester River. You'll enjoy the large back balcony with views of historic Chestertown. The third level could be used as the primary bedroom; there is a large full bathroom and closet. The townhomes have a private driveway, so you'll never worry about finding a parking space. Take advantage of the easy access to Wilmer Park and Chestertown Marina, located just across the street. This townhouse is located in the heart of all Chestertown has to offer! Just a short distance to shops, restaurants, renowned bakeries, and the year-round farmers market by Fountain Park. You will have a front-row seat to the Downrigging Festival! Not to mention the many festivals held in downtown Chestertown throughout the year.
Welcome to 101 Birch Run Rd., Chestertown, MD! 3 Bedrooms 2 Full Baths Oversized 2-Car Garage .42 Acres Discover this stunning full-brick rancher located in the heart of historic Chestertown! Every inch of this 3-bedroom, 2-bath home has been completely updated with a sophisticated modern flair while maintaining an inviting, boutique-style warmth throughout. Step inside to find a bright, open-concept layout where the brand-new kitchen flows seamlessly into the family room-perfect for entertaining or relaxing by the cozy fireplace. The kitchen features sleek finishes, contemporary cabinetry, stylish lighting, and premium appliances. Both full baths have been fully renovated with todays top design trends, creating a spa-like experience at home. The homes thoughtful floor plan and attention to detail shine through every room-from fresh flooring and fixtures to elegant accents that elevate the overall aesthetic. Enjoy peace of mind with a new roof featuring 50-year architectural shingles (transferable warranty included). The oversized two-car garage provides ample space for parking and storage, while the landscaped .42-acre lot offers just the right amount of yard to enjoy without a lot of upkeep. Ideally situated within walking distance to the Chester River, Washington College, and Chestertowns charming downtown -boutiques, shops, restaurants, and regular community events await. Bring your boat, kayak, paddle-board, or jet ski and experience the best of Eastern Shore living!
Welcome to 107 Malone Ave. in the friendly community of Foxley Manor....A Great place to call "HOME"! This lovely 3 Bedroom, 1 Bath home is ready for you to make new memories, grow your family or downsize while enjoying single level living. Hardwood Floors throughout the living room and bedrooms have recently all been refinished. Through the front door is the well-lit family room with a large bay window allowing the beautiful outdoor views. Flow into the large kitchen with plenty of room for your kitchen table and you could even add a small island. Lots of counter space and cabinet space with all appliances included. There is plenty of room inside of the laundry room with the washer & dryer included as well! If you have a pet, there is a small to medium sized pet door that leads into the fenced in back yard. This home is located in between both of Chestertown's grocery stores, just off of Rt. 213, less than 2 miles to Downtown , 20 minutes to Rt. 301. Schedule your appointment to see your New Home!
Move-in ready and freshly updated in 2025! This 3-bedroom, 2-bath home offers approx. 1,600 sq. ft. of stylish living on a .387-acre corner lot with public water and sewer. Every detail has been thoughtfully upgraded-appliances and systems are brand new, complemented by luxury vinyl plank flooring throughout. The spacious layout includes a large mudroom and plenty of modern finishes. Located just minutes from Fairlee Creeks public landing for easy water access, and a short drive to downtown Chestertown and Rock Hall, this home combines comfort, convenience, and Chesapeake charm. PROPERTY CAN BE PURCHASED FOR AN ADDITIONAL COST WITH LISTING MLS #MDKE2005074, 1.8 ACRES SUBDIVIDED INTO 4 LOTS TO MAKE THIS LOT AN ESTIMATED TOTAL OF 2.19 ACRES!
READY TO FINISH!!! LVP Flooring installed on 10/04/2025 on the main and upper levels. Materials, fixtures, applicances cabinetry, washer/dryer and new toilet on site and ready to install. Discover the potential of 423 Calvert Street - a two-story, 1,136 sq. ft. townhouse built in 1992 and set on a 2,006 sq. ft. lot. This 3-bedroom, 1.5-bath home has already undergone major updates in 2025, including new flooring, appliances, fresh paint, and a newer roof. Renovations are well underway, with all remaining materials provided, giving the next owner an incredible opportunity to add the finishing touches. The property features a fenced front entry, a deep backyard with rear parking access, and plenty of outdoor space to enjoy. Ideally located near historic downtown Chestertown, youll find shopping, dining, entertainment, and events just minutes away, along with the waterfront park along the scenic Chester River and the nearby Washington College campus. Offered at just $185,000, this home presents exceptional value for use as a primary residence, a second home retreat, or an investment rental. All of this in Chestertown - a charming Eastern Shore community known for its rich history, vibrant arts scene, events, riverfront beauty, and welcoming small-town atmosphere.
YOUR DIAMOND IN ROUGH.........Home is original and needs updating through out....Priced to sell. Good bones, will need a buyer with vision. Main level has a large eat in kitchen, living room area and laundry room. Upper level has 3 bedrooms, 2 full bath; including master on suite. Large deck and fenced in back yard. Minutes from The Chester Bridge.