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Real Estate & Property for Sale in Chestertown
Most Recent
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Under Contract
$749,000
415 Eagle Manor Drive
Church Hill MD 21623
Single-Family
Listing courtesy of RE/MAX Executive
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For Sale
$1,150,000
231 Richard Drive
Chestertown MD 21620
Single-Family
Listing courtesy of TTR Sotheby's International Realty
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SoldMar 5, 2026
$165,000
6179 Dorlon Drive
Edesville MD 21661
Single-Family
Listing courtesy of Chesapeake Real Estate Associates, LLC and RE/MAX Executive
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SoldMar 4, 2026
$190,000
Hoffecker Rd
Chestertown MD 21620
Land
Listing courtesy of Chesapeake Real Estate Associates, LLC and EXIT Preferred Realty
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Pending
$124,900
21324 Persimmon Drive
Chestertown MD 21620
Townhouse
Listing courtesy of Coldwell Banker Realty
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SoldMar 2, 2026
$125,000
423 Calvert Street
Chestertown MD 21620
Townhouse
Listing courtesy of Redfin Corp and Compass
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For Sale
$200,000
1B/117 North Water Street
Chestertown MD 21620
Condo
Listing courtesy of TTR Sotheby's International Realty
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SoldFeb 27, 2026
$120,000
141 Prospect St
Chestertown MD 21620
Single-Family
Listing courtesy of Taylor Properties and Chesapeake Real Estate Associates, LLC
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SoldFeb 27, 2026
$650,000
109 S Water St
Chestertown MD 21620
Townhouse
Listing courtesy of Cross Street Realtors LLC and TTR Sotheby's International Realty
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SoldFeb 26, 2026
$364,900
108 Flying Cloud Drive
Chestertown MD 21620
Single-Family
Listing courtesy of Cross Street Realtors LLC and Coldwell Banker Realty
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SoldFeb 25, 2026
$765,000
25999 Lambs Meadow Rd
Worton MD 21678
Single-Family
Listing courtesy of TTR Sotheby's International Realty and Monument Sotheby's International Realty
For Sale
$750,000
201 North Lynchburg Street
Chestertown MD 21620
Land
Listing courtesy of RE/MAX Associates-Hockessin
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For Sale
$650,000
124 Piper Court
Church Hill MD 21623
Single-Family
Listing courtesy of Berkshire Hathaway Homeservice Homesale Realty
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SoldFeb 20, 2026
$800,000
4671 Cliffs City Road
Chestertown MD 21620
Single-Family
Listing courtesy of Cummings & Co. Realtors and Unrepresented Buyer Office
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SoldFeb 20, 2026
$99,900
224 Main St
Church Hill MD 21623
Single-Family
Listing courtesy of Doug Ashley Realtors, LLC
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Under Contract
$750,000
118 Dabbling Court
Church Hill MD 21623
Single-Family
Listing courtesy of Samson Properties
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SoldFeb 19, 2026
$270,000
24339 Chestertown Road
Chestertown MD 21620
Single-Family
Listing courtesy of Doug Ashley Realtors, LLC and Chesapeake Real Estate Associates, LLC
SoldFeb 19, 2026
$11,000
Caulks Field Rd
Georgetown MD 21620
Land
Listing courtesy of Long & Foster Real Estate, Inc. and Select Land & Homes, LLC
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SoldFeb 18, 2026
$260,000
134 Char Nor Manor Boulevard
Chestertown MD 21620
Single-Family
Listing courtesy of Meredith Fine Properties and Doug Ashley Realtors, LLC
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SoldFeb 17, 2026
$1,524,900
10800 Cliff Rd
Chestertown MD 21620
Single-Family
Listing courtesy of Taylor Properties and RE/MAX Chesapeake
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For Sale
$235,000
25044 Travis Trail
Butlertown MD 21678
Single-Family
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company
127 - 147 of 427
Suburbs in Chestertown
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- (619) 566-0008