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

View from the waterfront of 98 cannon street restaurant in Chestertown, Maryland

98 Cannon Street, Chestertown, MD 21620

5, 094 SQFT | .42 ACRES

$690,000

View from the street of 221 Old Bridge Road in Chestertown, Maryland

221 Old Bridge Road, Chestertown, MD 21620

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

$359,900

Aerial front view of 500 Washington Avenue in Chestertown, Maryland

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

Explore the Lifestyle

Check out recent posts about Chestertown including insider insights, local guides, and real estate advice.

Retiring in Chestertown, MD: What to Know Before You Make the Move

Eastern Shore Fall Scenery

A Local’s Guide to Chestertown This Fall (Beyond the Festivals)

Street view of Downtown Chestertown, MD

Living in Kent County: A Realtor’s Perspective

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