Chestertown Real Estate

23043 Bay Shore Spur

$385,000

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Most Expensive

6324 Quaker Neck Road

$2,895,000

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Least Expensive

Chestertown Listings Summary

Chestertown - Town vs. County Stats

Avg Price in Chestertown: $595,700 / County Avg $450,400

132%

Avg Taxes in Chestertown: $4,600 / County Avg $2,100

220%

Avg Sq. Ft. in Chestertown: 2,038 / County Avg 2,189

93%

Avg Price per/sqft in Chestertown:$292 / County Avg $206

142%

Avg Walkscore in Chestertown: 18 / County Avg 25

74%

Avg Year Built in Chestertown: 1954 / County Avg 1984

99%

Avg Days on Website in Chestertown: 143 / County Avg 157

91%

Chestertown Real Estate Market Health

New Listings

Reductions

Foreclosures

Short Sales

Neighborhoods in Chestertown MD
Chester Harbor
Chester River Landing
Chestertown
Chestertown Historic District
College Heights
Country Club Estates
Coventry Farms
Downtown Chestertown
Fairlee
Historic Chestertown
Langford
Mile Tree Village
Orchard Hill
Prestwick
Quaker Estates
The Grove
Tolchester
Tolchester Estates
Washington Park

Bowie Office

16701 Melford Blvd, Ste 100
Bowie, MD 20715

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The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which participates, and is provided by BRIGHT through a licensing agreement.

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Data last updated: November 6, 2026 4:38 PM UTC

Some properties which appear for sale on this website may no longer be available because they are under contract, have Closed or are no longer being offered for sale.

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