Chestertown Real Estate

23043 Bay Shore Spur

$385,000

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8796 Maryland Parkway

$1,495,000

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Least Expensive

Chestertown Listings Summary

Chestertown - Town vs. County Stats

Avg Price in Chestertown: $584,600 / County Avg $465,300

126%

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

203%

Avg Sq. Ft. in Chestertown: 2,064 / County Avg 2,196

94%

Avg Price per/sqft in Chestertown:$283 / County Avg $212

134%

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: 137 / County Avg 155

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
Great Oak Estates
Heather Heights
Historic Chestertown
Mile Tree Village
Orchard Hill
Quaker Estates
Quaker Neck
Tolchester
Tolchester Estates
Washington Park

Weichert, Realtors® - Blue Ribbon (DMV)

94 Old Mills Rd
Martinsburg, WV 25401

Weichert, Realtors® - Blue Ribbon Front Royal

134B Peyton Street
Front Royal, VA 22630

Weichert, Realtors® - Blue Ribbon Bowie

4201 Mitchellville Rd, Suite 203
Bowie, MD 20716

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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 18, 2026 4:06 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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Kanawha Valley Board of REALTORS® 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 Weichert, Realtors® - Blue Ribbon (DMV) 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 18, 2026 7:55 PM UTC