Chestertown Real Estate

23043 Bay Shore Spur

$385,000

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Most Expensive

6324 Quaker Neck Road

$2,895,000

Save View Details Similar Properties

Least Expensive

Chestertown Listings Summary

Chestertown - Town vs. County Stats

Avg Price in Chestertown: $621,500 / County Avg $469,500

132%

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

210%

Avg Sq. Ft. in Chestertown: 2,122 / County Avg 2,201

96%

Avg Price per/sqft in Chestertown:$293 / County Avg $213

137%

Avg Walkscore in Chestertown: 18 / County Avg 23

79%

Avg Year Built in Chestertown: 1955 / County Avg 1984

99%

Avg Days on Website in Chestertown: 134 / County Avg 154

87%

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
The Grove
Tolchester
Tolchester Estates
Washington Park

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All or a portion of the multiple listing information is provided by the Central Virginia Regional Multiple Listing Service, LLC, from a copyrighted compilation of listings. All CVR MLS information provided is deemed reliable but is not guaranteed accurate. The compilation of listings and each individual listing are ©2026 Central Virginia Regional Multiple Listing Service, LLC. All rights reserved. All MLS listings are © 2026 Central Virginia Regional Multiple Listing Service, LLC. All rights reserved. No one may copy and/or repost these MLS listings, or any portion thereof, without the written permission of an authorized officer of the Central Virginia Regional Multiple Listing Service, LLC. All listings with the CVRMLS logo are provided courtesy of the IDX program. Last Updated: September 23, 2026 10:24 PM UTC Show More...

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Information Deemed Reliable But Not Guaranteed

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.

The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Data last updated: September 23, 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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