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.
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.
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.
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.
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.
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.
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.
