Chestertown is a town in Kent County, Maryland, United States. The population was 5,532 as of the 2020 census. It is the county seat of Kent County, the oldest county in Maryland. [4][5]

Jun 7, 2025 · Chestertown is once again looking for a new Town Manager. Earlier in 2025, the former manager had provided ample notice of his resignation, and a formal search process …

With a colonial history dating back to the 17th century, Chestertown, Maryland is proud of its maritime heritage. Sitting on the banks of the Chester River, sailing ships can still be seen …

Dec 15, 2025 · Discover the charm of Chestertown, Maryland! Explore local businesses, historic sites, and vibrant community events in the heart of our waterfront town.

Founded in 1706, Chestertown is a historic college town along the banks of the Chester River on Maryland's Eastern Shore. The brick sidewalks lined with shops, restaurants and inns …

Nov 11, 2025 · Chestertown, Maryland, is a charming small town filled with history, creativity, and outdoor fun. Located on the beautiful Chester River, it offers something for everyone, from art …

Chestertown is an unforgettable destination along the Eastern Shore of Maryland. The area is home to countless outdoor activities, making it the ideal place for wildlife viewing, hiking, …

Jan 14, 2025 · Chestertown is one of the oldest counties in Maryland, having been established as early as 1706 and characterized by brick sidewalks and antique shops lining the roads.

Realtor.com® has 116 homes for sale in Chestertown, MD. The median listing price is $307,000. Browse the latest listings and find your dream home today.

Chestertown, the county seat of Kent, the Eastern Shore of Marylands's oldest county, was founded in 1706 and served as a port of entry during colonial times. A town rich in history, its …