$441,448Average Value$217Average Price per Sq Ft33Homes 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
Retha Arrabal,
an experienced agent in this area.
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On average, homes in Chestertown, MD sell after 48 days on the market compared to the national average of 55 days. The median sale price for homes in Chestertown, MD over the last 12 months is $367,500, up 2% from the median home sale price over the previous 12 months.
Welcome home to historic Chestertown. This beautiful 5 bedroom colonial is located just one block from Washington College. Relax on your welcoming mahogany front porch before stepping inside this pristine home. Features a beautifully updated kitchen. Fresh exterior paint gleams. Iconic slate roof adds timeless appeal. Enjoy the private, fenced backyard oasis, meticulously landscaped for outdoor
Mary CarlisleColdwell Banker Chesapeake Real Estate Company
Brand new home in Historic Chestertown available for move-in now. This interior unit features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitchen with white shaker cabinets, granite countertops, and stainless steel appliances, plus a covered patio off the kitchen for outdoor enjoyment. Upstairs you'll find generously sized bedrooms including a large primary suite with
Welcome to Chesapeake Landing! Come see this amazing home offering vaulted ceilings, huge master bath, open concept, plenty of closet space, laminate flooring, and a private secluded fenced lot. Located in a water oriented neighborhood with community boat ramp and pier and nearby restaurants and marina. Move here and enjoy all the Eastern Shore has to offer!
Custom-built home in Country Club Estates with beautiful architectural details. Spacious open living space with hardwood floors and wooden beams, glowing with ample natural light! Enjoy time on the large screened porch, finished with Ipe hardwood, overlooking the peaceful creek, woods and park like setting. Five bedrooms and 4 full bathrooms, nicely designed with privacy in mind. There's an
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
Nice cleared building lot in an established community. Public water and sewer available. Property recently acquired through tax sale foreclosure. Law Firm of Shaw and Crowson P.A. in Salisbury preferred for settlement.
This 3-bedroom, 1-bathroom ranch-style home in Quaker Estates offers a solid investment opportunity with a total finished area of 936 sq ft. Built in 1963, the property features essential appliances including a refrigerator and stove, ensuring immediate functionality for tenants or future buyers. The average condition of the home allows for potential value-add renovations, which can significantly
(Lot 2 - .685 acres & Lot 3 - .689 acres) Conveniently located slightly off 291, in a private area on a dead-end road, this property is close to Chestertown and minutes away from route 301. Lots sit high off the road level and adorned with young saplings. Soil evaluation from 2011 approved for 3 beds and a 2,000 sq ft home, located just outside the critical area. Unsuccessful land evaluation
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
Back on the market due to buyer's failure to perform. Due diligence was done with the County as far as hooking up to the septic system but verify with Kent County Public Works. The corners have been marked and survey is in the documents tab. E Georgetown Rd - Parcel 70, Chestertown MD consists of 3 acres. Public water/sewer hookup is available through Kent County. Loads of opportunities for a
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
**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
**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
Ground floor apartment in nice, safe, quiet, upscale area 2 blocks from river and waterfront park, 1 block from downtown (in Historic District). Suitable for 1 person. No pets or smoking.
Cute 4 bedroom 2 bathroom Cape Cod in the quiet Crestview neighborhood in Chestertown close to Restaurants, Shopping, the brand new YMCA and the Historic District. Eat in kitchen with back deck overlooking a beautiful yard that backs up to farm land that is preserved forever. Freshly painted and new carpet! Washer & dryer in unit. Extra storage in knee walls upstairs. $25 application fee per
Welcome to 128 N Queen Street, Unit 2. Utilities included!!!A beautiful Victorian apartment located downtown Chestertown within walking distance to the Chester River and situated close to the Washington College. 2nd floor private unit with spacious living area, separate dining room, galley kitchen, full bathroom and bedroom. All with a fresh coat of paint! Unit is available immediately,
Entire historic home in downtown Chestertown for a great price!! One block from shops, restaurants, galleries and much more. Large living room opens to eat-in kitchen with beautiful countertops and all stainless steel appliances. Half bath and laundry on main floor and 3 bedrooms and two full bathrooms upstairs. Hardwood floors throughout. Private backyard with fence and storage shed. Dead end
Joseph CiganekColdwell Banker Chesapeake Real Estate Company
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
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
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