Chestertown Real Estate

23043 Bay Shore Spur

$385,000

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8796 Maryland Parkway

$1,495,000

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Chestertown Listings Summary

Chestertown - Town vs. County Stats

Avg Price in Chestertown: $592,600 / County Avg $466,000

127%

Avg Taxes in Chestertown: $4,700 / County Avg $2,100

222%

Avg Sq. Ft. in Chestertown: 2,253 / County Avg 2,231

101%

Avg Price per/sqft in Chestertown:$263 / County Avg $209

126%

Avg Walkscore in Chestertown: 18 / County Avg 23

79%

Avg Year Built in Chestertown: 1954 / County Avg 1985

98%

Avg Days on Website in Chestertown: 138 / County Avg 150

92%

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
Double Creek Woods
Fairgale Properties
Fairlee
Foxley Manor
Great Oak Estates
Heather Heights
Historic Chestertown
Mile Tree Village
Orchard Hill
Quaker Neck
Tolchester
Tolchester Estates

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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: August 24, 2026 5:10 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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