Chestertown Real Estate

23043 Bay Shore Spur

$385,000

Save View Details Similar Properties

Most Expensive

8796 Maryland Parkway

$1,495,000

Save View Details Similar Properties

Least Expensive

Chestertown Listings Summary

Chestertown - Town vs. County Stats

Avg Price in Chestertown: $579,500 / County Avg $557,600

104%

Avg Taxes in Chestertown: $4,300 / County Avg $4,000

109%

Avg Sq. Ft. in Chestertown: 2,040 / County Avg 2,051

99%

Avg Price per/sqft in Chestertown:$284 / County Avg $272

104%

Avg Walkscore in Chestertown: 18 / County Avg 25

73%

Avg Year Built in Chestertown: 1954 / County Avg 1960

100%

Avg Days on Website in Chestertown: 139 / County Avg 119

117%

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

Anne Arundel Properties

175 Admiral Cochrane Dr Suite 112
Annapolis, MD 21401

Should you require assistance in navigating our website or searching for real estate, please contact our offices at 301-970-2447.

MLS® Disclaimer

© BRIGHT, All Rights Reserved

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 21, 2026 12:41 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.

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...