Living in Chestertown | Housing, Restaurants, Attractions | Long & Foster

Living in Chestertown, MD

If you're a history buff, fond of cobblestone streets and gas-lit lanterns, you'll love living in Chestertown, Maryland. Founded in 1706, it was named one of Maryland's six "royal ports of entry" in the 18th century. Shortly after the Boston Tea Party, Chestertown citizens resolved to prohibit buying, selling, or drinking tea, and they were even said to have held their own tea party on the Chester River. Besides its active history, the town has many amenities and activities, and with its idyllic location and natural beauty, you're bound to love living in Chestertown.

book plate chestertown md

Things to Do in Chestertown

Modern-day residents of Chestertown, Maryland, pay homage to that long-ago Boston Tea Party-inspired protest each Memorial Day weekend with the Chestertown Tea Party Festival. Folks from all over the region congregate in Chestertown, MD, for this unique event that's packed with colonial artisans and vendors, food, music, a parade, raft races, and more. The highlight of the festival is a reenactment during which costumed revelers throw tea into the Chester River.

Chestertown residents enjoy other annual festivals and annual events, too, including the RiverFest arts festival in September and National Music Festival in June. The latter is held at Washington College, a private liberal arts college established in 1782 and the 10th-oldest college in the country. From March through December, locals head to Fountain Park for the farmers market, where they shop and linger with their neighbors. Boating, swimming, and waterfront dining are also popular, especially when it's warm. Many restaurants serve up oysters and other seafood plucked from nearby Chesapeake Bay.

The arts are in season year-round, thanks to events sponsored by the Historical Society of Kent County. A couple of the most popular events include guided, lantern-led ghost walks in October and History Happy Hours the first Friday of each month; during happy hour, attendees enjoy wine, cheese, and lively programming and discussions. Chestertown, Maryland, is also home to the Schooner Sultana, a replica of a 1768 tall ship that's maintained by the Sultana Education Foundation. The foundation's public programming includes opportunities for day sails and downrigging weekends.

gallery chestertown md

Chestertown Real Estate

If living in a historic, small city convenient to the East Coast's urban hubs appeals to you, check out the diverse Chestertown real estate market. Not only is a Chestertown neighborhood a place where you'll get to know your neighbors, you'll also be able to live by the water if you choose. You'll find estate homes for sale in Chestertown, and also a wide variety of cozy cottages and bungalows, waterfront condos, affordable apartments, and single-family homes in subdivisions. 


Getting There & Around


What Locals Love

Don't Miss It

  • There’s no shortage of exciting festivals and annual events here, including the Chestertown Tea Party Festival, RiverFest Arts Festival, and the National Music Festival.
  • Outdoorsy types enjoy going for a dip or taking the powerboat out for a spin along the Chesapeake Bay.
  • The Historical Society of Kent County sponsors a variety of fun events throughout the year, including History Happy Hours and guided, lantern-led ghost tours in October.


Chestertown Real Estate at a Glance

  • 62 Homes Sold*
  • 73 Avg. Days on Market*
  • $440,000 Median Price*

*over last 3 months

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There Are 78 Properties Available in Chestertown



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