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: $614,500 / County Avg $468,000

131%

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

211%

Avg Sq. Ft. in Chestertown: 2,113 / County Avg 2,197

96%

Avg Price per/sqft in Chestertown:$291 / County Avg $213

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: 137 / County Avg 154

89%

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 Central

2333 Welsh Road
Lansdale, PA 19446

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The data relating to real estate for sale on this web site includes listings held by MLS-IDX Participants of the Internet Data Exchange program of the Multiple Listing Service of the Pocono Mountains Association of Realtors®. Listings marked with the Internet Data Exchange logo are not necessarily the listings of the owner of this web site. All listing data is the copyrighted property of the aforesaid Association and its MLS-IDX Participants with all rights reserved. The information contained herein is believed to be accurate, but no warranty as such is expressed or implied. 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 22, 2026 3:50 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.

Some real estate firms do not participate in IDX and their listings do not appear on this website. Some properties listed with participating firms do not appear on this website at the request of the seller. Show More...