$446,365Average Value$221Average Price per Sq Ft30Homes For Sale
Chestertown's river access and historic charm draws homebuyers
Founded in 1706, Chestertown was once a prominent port on the Chester River. Today, commerce has slowed on Maryland’s Eastern Shore, but the community’s maritime spirit remains a draw for homebuyers, especially those looking to escape the bustle of mid-Atlantic cities. “There are a lot of second homes for people who live in Washington and Philadelphia,” says John Burke, associate broker with Gunther McClary Real Estate, who has sold homes in the area for over two decades. Chestertown’s river access and historic charm — plus the energy of Washington College, a small liberal arts school in town — appeal to full-timers and part-timers in Kent County.
Chestertown residents take advantage of being next to Chester River.
Music Life is a local music shop right downtown in historic Chestertown.
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Victorian homes downtown, plus waterfront properties
Downtown Chestertown lies along the river, with homes often dating back to the late 1800s or the early 20th century. Waterfront homes are in the highest demand, offering beautiful views and convenient access to recreation. These sell for $840,000 to $1.1 million. Queen Anne and Colonial Revival styles are found throughout the rest of downtown, with these homes selling for $360,000 to $680,000. Farther inland, midcentury and more contemporary builds are common. Ranch-style homes sell for $240,000 to $530,000, while New Traditional houses go for $250,000 to $660,000, based on size.
Victorian style homes with plenty of character can be found throughout Chestertown.
Waterfront properties in Chestertown often have dock access right from their backyards.
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Recreation revolves around the river with marinas and waterfront parks
Access to the Chester River is a selling point for the community, and many residents own boats. Riverfront homes often have docks or piers, and the town operates a public marina with boat slips for rent. The private Chester River Yacht & Country Club is just south of downtown, featuring an 18-hole golf course, a private marina and amenities like a pool and a restaurant. City parks include the waterfront Wilmer Park, which has a walking trail and a playground. Bikers and joggers can head out on the Wayne Gilchrest Trail, which runs roughly 2 miles through Chestertown on an old rail bed.
Dock your boat at the Chestertown Marina and have a fun day out on the river.
A steel art installation greets residents into Wilmer Park.
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Local restaurants and boutiques throughout downtown
High Street is the main drag through downtown. Trees shade brick sidewalks, leading to the boutiques and restaurants that occupy historic storefronts. Locally owned restaurants, like the Kitchen at the Imperial or Watershed Alley, tend to feature seafood-heavy specialties. Locals and visitors frequent the area’s galleries, gift shops and bookstores. Outside downtown, shopping centers sit across from Washington College. The Acme Markets grocery store is located in Kent Plaza alongside a few fast-food spots.
Kingstown friends catch up at The Kitchen at The Imperial in Chestertown.
Kingstown finds great clothing at Mimi's Closet in Chestertown.
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Annual festival celebrates the legendary Chestertown Tea Party
In 1774, the British government closed the port of Boston as punishment for the famous Boston Tea Party. Chestertown, at the time a major port in its own right, responded. “It’s little known, but after the Boston Tea Party, Chestertown had its own tea party,” Burke says. Today, the local protest is reenacted as part of the Chestertown Tea Party Festival, held every Memorial Day Weekend. The event includes a Colonial parade, live music and a beer garden. Burke also mentions the Sultana Downrigging Festival, which features a flotilla of schooners in the Chester River as well as live bluegrass music back ashore. Residents can also attend Washington College sporting events, including home games for the school’s NCAA DIII lacrosse team, winner of two national championships.
Enjoy live music and other festivities at the Chestertown Tea Party Festival in Chestertown, MD.
Enjoy a parade that marches through downtown Chestertown for the Tea Party Festival.
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Education at Kent County schools, as well as Washington College
The Kent County Public Schools system serves Chestertown, receiving a C-plus overall grade from Niche. Students can start at H. H. Garnett Elementary before heading to Kent County Middle and Kent County High, each rated C-plus. Kent County High offers roughly a dozen Advanced Placement courses, giving students the opportunity to earn college credit. Washington College, a private liberal arts institution with approximately 1,000 undergraduates, is also in Chestertown. “Lots of people who go to Washington College actually end up sticking around after they graduate, or moving back later,” Burke says.
H.H. Garnett Elementary School has 344 students in grades PK-5.
Kent County High School has 558 students in grades 9-12.
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Walkable downtown within a drive of larger cities
The parks and restaurants in downtown Chestertown are pedestrian-friendly. While the Maryland Upper Shore Transit system offers limited bus services toward Rock Hall in one direction and Easton in the other, locals generally drive to destinations outside Chestertown. Baltimore is 75 miles away, and Baltimore/Washington International Airport has the closest flights. The University of Maryland Shore Medical Center, located in Chestertown, has an emergency room as well as other specialties.
A drawbridge connects Chestertown and Kingstown.
BWI is only 30 minutes from Patterson Park.
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Written By
Brendan Doyle
Photography Contributed By
Bill Marrs
Interested in learning more about homes in this area?
Reach out to
Tinamarie Reamy,
an experienced agent in this area.
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On average, homes in Chestertown, MD sell after 50 days on the market compared to the national average of 54 days. The median sale price for homes in Chestertown, MD over the last 12 months is $375,000, up 1% from the median home sale price over the previous 12 months.
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
PRICE IMPROVEMENT ON THIS QUICK MOVE-IN LUXURY VILLA! $5000 towards closing. This stunning 4-bedroom villa offers a welcoming and functional layout with exceptional upgrades and finishes throughout. The main level features an oversized family room that opens to the kitchen and dining area—perfect for entertaining or everyday living. The upper level includes three spacious bedrooms, including an
Rebuilt in 1863, the Tilley Residence showcases classic Second Empire architecture on one of Chestertown’s most prominent historic corners near Widehall and the Custom House. Completely restored in 2024–2025 by one of the town’s most iconic builders, the home blends historic character with modern comfort through thoughtful updates, new systems, and refined living spaces. Just one block to the
Murphy ONeillColdwell Banker Chesapeake Real Estate Company
Here’s the opportunity buyers wait for. A classic Colonial in sought-after Coventry Farms, priced where this neighborhood rarely plays, offering space, comfort, and the chance to build equity while you live well. Step inside and you’re welcomed by a warm, traditional layout that just feels right. Accent walls add personality, the formal dining room sets the stage for holidays and celebrations,
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
Welcome to Coventry Farms in Chestertown — where comfort, elegance, and space come together in this stunning colonial-style home! Built in 2009 and meticulously maintained, this spacious property offers over 4,000 square feet of finished living space across three levels — including a fully finished basement with a full bath, perfect for entertaining, a guest suite, or a home office setup Curb
Welcome to “The Cottage,” as it’s affectionately known! This charming home offers beautiful water views of the Chesapeake Bay, creating a peaceful and relaxing place to call home. Inside, you’ll find a bright and inviting layout featuring a Florida Room, a spacious dining room with a cozy fireplace, and two comfortable bedrooms. The large living room is filled with natural light and showcases
Welcome to 24775 Langford Rd, a quiet countryside retreat just minutes from downtown Chestertown. This well-maintained three-bedroom, one-bath home sits on 1.27 acres and offers a peaceful setting with ample outdoor space. The property features a generously sized three-car detached garage/workshop and a large Trex deck with hot tub, ideal for relaxing or entertaining. In 2018, the home underwent
Buildable waterfront lot in the Chester River Landing community. This prime location captures panoramic views of the Chester River! Just steps away from deep water boat slips, which are available for lease or purchase. Perfect location to build your dream home on the water. The Chester River Landing community amenities include docks, in-ground pool, grilling and outdoor dining area right on the
E Georgetown Rd - Parcel 70, Chestertown MD consists of 3 acres. Public water/sewer hookup is available through Kent County. Call listing agent for more information regarding this offering. Loads of opportunities for a private wooded oasis. Located about 15 minutes from Chestertown or Rock Hall.
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
**Price increase due to the home’s expanded footprint—over 1,200 additional square feet!** **To be built! Welcome to this beautifully designed 3,540 sq. ft. home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The standard floor plan includes 4 bedrooms and 3.5 baths, with the option to expand to 5 bedrooms and 4.5 baths by adding a first-floor
Newly constructed three-bedroom townhome with fantastic water views from the living level and bedrooms! Spacious open living space featuring 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. You'll love the warm hardwood floors throughout the
**To be built! 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
**To be built! Welcome to this beautifully designed 1,964 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, gourmet kitchen, and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like
If you’ve been searching for an open‐concept apartment with a stunning view, your search ends here. This fully renovated third‐floor residence delivers modern style, thoughtful updates, and an airy layout that feels instantly welcoming. Step into a beautifully redesigned kitchen featuring ample cabinetry, upgraded appliances, and a spacious island perfect for cooking, gathering, or entertaining.
Property Id: 2151738This secluded home sits quietly on a family farm nestled on the bank of Morgnec creek. Built in 1990, it has 4 bedrooms and 2 baths with a full basement for storage. Although no pets are allowed, you can enjoy watching the wildlife walk through your yard while you sit outside on the deck. If interested, call or text Chris with Kendall Properties at . Credit checks and
Welcome to 509 Cannon Street! This cozy 2-bedroom, 1-bath home has been thoughtfully updated and is ready for you to move right in. Inside, you'll find a comfortable layout and a brand-new HVAC system to keep you comfortable year-round, plus the convenience of off-street parking. Tenants are responsible for electric, town water and sewer, and internet services. To qualify, applicants must have a
William SuttonColdwell Banker Chesapeake Real Estate Company
Property Id: 1453253Bright, open, newly remodeled, two bedroom apartment in downtown Chestertown. Open kitchen/living/dining room, flooded with light. Kitchen has stainless appliances, including dishwasher, and granite counters. Two large bedrooms, plentiful storage space. In-unit washer and dryer. The building has recently undergone extensive renovations, with many energy improvements,
One, two and three bedroom apartments located near Washington College, wellness/ rehab center, Churches, shopping and a short walk to downtown Chestertown. Short distance to the Chester River and Chesapeake Bay. Immediate Availability.
Property Id: 1426365A modern apartment in the heart of Chestertown. Blocks from Fountain Park and Washington College, this third floor, 2 bedroom apartment is in a building that was recently renovated to the studs, with modern windows and HVAC and original features, such as wood floors and exposed beams. In-building laundry and shared yard for tenants' use. Available immediately. Landlord
This property features 1200 square feet of living space, including one bathroom and 2 designated bedrooms. The unit comes fully furnished and is smoke-free, providing a clean and comfortable environment. Key amenities include air conditioning for climate control, a dishwasher for convenient meal cleanup, and an in-unit washer and dryer for laundry needs. The living area is spacious, allowing for
This is a perfect little house in the country on a 1 acre secluded lot 1 1/2 miles from Chestertown. It is brand new on the inside with high end finishes. New Anderson windows, new doors, tile and laminate floors, SS appliances, granite countertops, Rinnai hot water heater, mini split heat pump, Owner will cut grass and maintain exterior ( 2 tomato plants) for one year, high speed internet
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