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: $620,300 / County Avg $468,500

132%

Avg Taxes in Chestertown: $4,600 / County Avg $2,200

211%

Avg Sq. Ft. in Chestertown: 2,123 / County Avg 2,193

97%

Avg Price per/sqft in Chestertown:$292 / County Avg $214

137%

Avg Walkscore in Chestertown: 18 / County Avg 23

79%

Avg Year Built in Chestertown: 1954 / County Avg 1984

98%

Avg Days on Website in Chestertown: 138 / County Avg 156

88%

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 1st Advantage

6375 Mercury Dr
Mechanicsburg, PA 17050

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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 23, 2026 3:16 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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All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of the Multiple Listing Service. Real estate listings held by brokerage firms other than REMAX 1st Advantage may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. Copyright ©2026 All rights reserved. Last Updated: September 23, 2026 6:14 PM UTC Show More...