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: $577,700 / County Avg $468,200

123%

Avg Taxes in Chestertown: $4,400 / County Avg $2,200

199%

Avg Sq. Ft. in Chestertown: 2,050 / County Avg 2,197

93%

Avg Price per/sqft in Chestertown:$282 / County Avg $213

132%

Avg Walkscore in Chestertown: 18 / County Avg 23

79%

Avg Year Built in Chestertown: 1954 / County Avg 1984

99%

Avg Days on Website in Chestertown: 139 / County Avg 154

90%

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

REMAX One

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Data last updated: September 21, 2026 11:33 AM UTC

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