Homes for Sale in Chestertown, Maryland
Chestertown is one of Maryland’s most historic towns — a charming, walkable community with colonial architecture, vibrant arts, and waterfront charm along the Chester River.
Current Properties in Chestertown:
There are currently no properties for sale by Courtney Chipouras in Chestertown.
There are currently no properties for sale by Courtney Chipouras in Chestertown.
Homes Recently Sold by Courtney in Chestertown, MD

98 Cannon Street, Chestertown, MD 21620
5, 094 SQFT | .42 ACRES
$690,000

221 Old Bridge Road, Chestertown, MD 21620
3 BD | 2 BA | 1,851 SQFT | 0.51 ACRES
$359,900

500 Washington Avenue, Chestertown, MD 21620
2,414 SQFT | .482 ACRES
$275,000

24415 Chestertown Road, Chestertown, MD 21620
2 BD | 1 BA | 1,110 SQFT | 1 ACRE
$264,900
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About Courtney Chipouras, Realtor
As a local real estate agent with deep roots in the Chesapeake Bay area, Courtney Chipouras brings professionalism, integrity, and insider knowledge to every transaction. Whether buying, selling, or investing in Chestertown real estate, she's your go-to guide.








