Chestertown Real Estate
Most Popular
23043 Bay Shore Spur
$385,000
Most Expensive
8796 Maryland Parkway
$1,495,000
Least Expensive
234 N College Avenue
$85000
Chestertown Listings Summary
Chestertown - Town vs. County Stats
Avg Price in Chestertown: $582,800 / County Avg $462,100
126%
Avg Taxes in Chestertown: $4,400 / County Avg $2,100
207%
Avg Sq. Ft. in Chestertown: 2,077 / County Avg 2,194
95%
Avg Price per/sqft in Chestertown:$281 / County Avg $211
133%
Avg Walkscore in Chestertown: 18 / County Avg 23
79%
Avg Year Built in Chestertown: 1953 / County Avg 1984
98%
Avg Days on Website in Chestertown: 141 / County Avg 155
91%
Chestertown Real Estate Market Health
New Listings
Reductions
Foreclosures
Short Sales
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
Charlottesville Area Association 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
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