Properties For Sale in Chestertown

Price Improvement! Spectacular waterfront on the Chester River!! Words can't describe the uniqueness of this property. With the historic charm of an older home but high end modern upgrades, you will be living the life of luxury. Spacious rooms, magnificent views of the Chester River and your priv...

Rebuilt in 1863, the Tilley Residence showcases classic Second Empire architecture on one of Chestertown's most prominent historic corners across from the Custom House, one of the first British Royal Ports of Entry to the Americas. Completely restored in 2025 by one of the Eastern Shore's iconic ...

Built in 1780/1840, Highcroft is in the heart of the Historic District near the Chester River. A rare in-town property that offers a 2-car garage with a second floor and a long driveway for tons of off-street parking. 3 bedrooms, 4 full baths and 1 half bath. Primary bedroom has his and hers priv...

This lovely Victorian, with peeks of the Chester River, has been updated and remodeled while keeping many of the original features. These include stunning parquet floors, hardwood floors, bulls eye moldings, wainscoting, built-ins and more. The front parlor has a gas fireplace and there are pocke...