Chestertown Real Estate

23043 Bay Shore Spur

$385,000

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Most Expensive

6324 Quaker Neck Road

$2,895,000

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Least Expensive

Chestertown Listings Summary

Chestertown - Town vs. County Stats

Avg Price in Chestertown: $621,400 / County Avg $469,300

132%

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

211%

Avg Sq. Ft. in Chestertown: 2,122 / County Avg 2,199

96%

Avg Price per/sqft in Chestertown:$293 / County Avg $213

137%

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: 135 / County Avg 157

86%

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
The Grove
Tolchester
Tolchester Estates
Washington Park

Smart Realty, LLC

1700 Elton Rd
Silver Spring, MD 20903

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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.

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Data last updated: September 25, 2026 8:34 AM UTC

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