Chestertown, MD Homes & Real Estate

Chestertown is the county seat of Kent County, Maryland, on the Chester River on the Eastern Shore. The historic district has brick townhouses, Georgian homes and a High Street lined with shops and restaurants, and a college campus sits next to the river.

Route 213 is the main road, running north toward Chesapeake City and south toward Centreville, and Route 20 heads west to Rock Hall and the Chesapeake Bay. Route 291 and Route 297 lead to nearby villages. The Chesapeake Bay Bridge is a drive south by way of Route 213 and US-301, and Wilmington and Dover are reachable by Route 301 and local roads.

The river is part of town life. Wilmer Park sits on the waterfront with grass, a pier and a place to launch small boats, and Fountain Park is a small park in the center of town. Boaters and paddlers use the Chester River, and the Eastern Neck National Wildlife Refuge near Rock Hall is a short drive. Shopping and dining are in the center and along Route 213, and UM Shore Medical Center at Chestertown is in town.

Housing includes historic homes in and around the town center, single-family neighborhoods built in the past several decades, waterfront and farm properties outside town, and some townhomes. Older and waterfront properties can need extra checking, and we review flood zone, septic and well status and inspection items for each home.

Kent County is quiet and spread out, so buyers often compare Chestertown with Rock Hall and Centreville for setting, drive time and price. We provide recent sales from nearby, show taxes and fees, and set up tours around your schedule. A free home value is the quickest first step if you are selling.