Chestertown Real Estate

23043 Bay Shore Spur

$385,000

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8796 Maryland Parkway

$1,495,000

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Chestertown Listings Summary

Chestertown - Town vs. County Stats

Avg Price in Chestertown: $578,500 / County Avg $464,000

125%

Avg Taxes in Chestertown: $4,400 / County Avg $2,100

206%

Avg Sq. Ft. in Chestertown: 2,092 / County Avg 2,191

95%

Avg Price per/sqft in Chestertown:$277 / County Avg $212

131%

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: 136 / County Avg 156

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
Double Creek Woods
Fairgale Properties
Fairlee
Foxley Manor
Great Oak Estates
Heather Heights
Historic Chestertown
Mile Tree Village
Orchard Hill
Quaker Estates
Quaker Neck
Tolchester
Tolchester Estates

Charles Town Saratoga Office

91 E Saratoga Dr Suite E
Charles Town, WV 25414

Should you require assistance in navigating our website or searching for real estate, please contact our offices at 304-930-5128.

Samson Properties. Nancy Williams, Broker. 91 E. Saratoga Drive Charles Town, WV 25414. 304.930.5128

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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 10, 2026 12:40 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...