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: $614,500 / County Avg $551,000

112%

Avg Taxes in Chestertown: $4,600 / County Avg $4,000

117%

Avg Sq. Ft. in Chestertown: 2,113 / County Avg 2,042

103%

Avg Price per/sqft in Chestertown:$291 / County Avg $270

108%

Avg Walkscore in Chestertown: 18 / County Avg 25

73%

Avg Year Built in Chestertown: 1954 / County Avg 1960

100%

Avg Days on Website in Chestertown: 137 / County Avg 118

116%

Chestertown Real Estate Market Health

New Listings

Reductions

Foreclosures

Short Sales

Neighborhoods in Chestertown MD
Byford Development
Chesapeake Landing
Chester Harbor
Chester River Landing
Chestertown
Chestertown Historic District
Country Club Estates
Coventry Farms
Crestview
Fairgale Properties
Fairlee
Foxley Manor
Heather Heights
Historic Chestertown
Mile Tree Village
Orchard Hill
Quaker Estates
Quaker Neck
Tolchester
Tolchester Estates
Washington Park

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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: September 22, 2026 8:02 AM 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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