Explore Homes for Sale in Chestertown, MD

Chestertown, MD offers a unique blend of historic charm, waterfront beauty, and small-town living on Maryland’s Eastern Shore. From Colonial-era homes in the heart of downtown to serene riverfront retreats, this area has something for every type of buyer. Explore current real estate listings and discover the lifestyle that makes Chestertown one of the Eastern Shore’s most sought-after destinations.