$447,343Average Value$214Average 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
Video By
Anthony Pesa
Interested in learning more about homes in this area?
Reach out to
David Landon,
an experienced agent in this area.
Agents Specializing in this Area
Sarah Miller
Hubble Bisbee Christie's International Real Estate
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On average, homes in Chestertown, MD sell after 47 days on the market compared to the national average of 57 days. The median sale price for homes in Chestertown, MD over the last 12 months is $375,000, down 1% from the median home sale price over the previous 12 months.
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
Price Improvement! Spectacular waterfront on the Chester River!! Words can't describe the uniqueness of this property. With the historic charm of an older home but high end modern upgrades, you will be living the life of luxury. Spacious rooms, magnificent views of the Chester River and your private dock with new boat lift, sandy beach, and stunning new saltwater pool. Exposed beams, scalamandre
Peter HellerColdwell Banker Chesapeake Real Estate Company
Rebuilt in 1863, the Tilley Residence showcases classic Second Empire architecture on one of Chestertown’s most prominent historic corners across from the Custom House, one of the first British Royal Ports of Entry to the Americas. Completely restored in 2025 by one of the Eastern Shore’s iconic builders, the home blends historic character with modern comfort through thoughtful updates, new
Murphy ONeillColdwell Banker Chesapeake Real Estate Company
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
Coventry Farms—Reduced to Sell, Offers EncouragedLocated in the highly desirable Coventry Farms community, this home presents a wonderful opportunity for its next owner to bring fresh vision and personal touches. With the seller preparing for a move out of the area, the property has been reduced to reflect its current condition and to encourage a timely sale. Inside, you’ll find generous
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
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 1,964 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
**To be built! 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
**To be built! 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
**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
**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
Custom builder selling his own home that has been well built, well maintained, and thoughtfully designed. This home is in great condition and offers just under 3,000 square feet of living space with 3 bedrooms and 2.5 baths. On everyone's wish list is the generous sized 2-car garage with extra side entrance. The first floor features an open and functional layout designed for everyday living. The
Welcome to your new home in the heart of Chestertown Maryland, a charming historic town nestled along the Chester River, known for its vibrant arts scene, waterfront dining, and small-town charm. This beautifully designed property blends modern finishes with timeless appeal. Step inside to find engineered hardwood floors flowing throughout the main living areas, creating both warmth and
Property Id: 2458980Built in 2023, this beautifully designed 4-bedroom, 2.5-bath home offers 2,056 square feet of modern living in a well-maintained, desirable neighborhood. Thoughtfully laid out with both comfort and functionality in mind, the home features open-concept living spaces, generous natural light, and well-proportioned bedrooms ideal for everyday living or working from
Welcome to your new home in the heart of Chestertown Maryland, a charming historic town nestled along the Chester River, known for its vibrant arts scene, waterfront dining, and small-town charm. This beautifully designed property blends modern finishes with timeless appeal. Step inside to find engineered hardwood floors flowing throughout the main living areas, creating both warmth and
Welcome to 128 N Queen Street, Unit 1. A beautiful Victorian apartment located downtown Chestertown within walking distance to the Chester River and situated close to the Washington College. First floor studio apartment. Unit is available immediately, utilities included: electric, water and sewer. Security Deposit plus one month rent (plus any proration) due at signing. Applications submitted via
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.
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.
Stunning 2 bedroom waterfront guest house just a short walk from Chestertown's historic district. Top to bottom exceptional interior design and brand new finishes from Stoltzfus Brothers Construction. Enjoy summer sunsets of the Chester River and Chestertown's timeless waterfront or take advantage of the dock and private water access. This guesthouse truly celebrates the water views from any
Joseph CiganekColdwell Banker Chesapeake Real Estate Company
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