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

221 Old Bridge Road, Chestertown Maryland

221 Old Bridge Road, Chestertown Maryland

3 BD | 2 BA | 1,851 SQFT | 0.51 ACRES

$369,900

24415 Chestertown Road, Chestertown Maryland

24415 Chestertown Road, Chestertown Maryland

2 BD | 1 BA | 1,110 SQFT | 1 ACRE

$264,900

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Courtney Chipouras, Eastern Shore Realtor

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.

 

Courtney Chipouras at her annual Pie Party event