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Real Estate & Property for Sale in Chestertown
Most Recent
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SoldFeb 13, 2026
$160,000
21316 Persimmon Drive
Chestertown MD 21620
Townhouse
Listing courtesy of Doug Ashley Realtors, LLC and Samson Properties
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Pending
$675,000
202/118 Little Harbor Way
Chestertown MD 21620
Condo
Listing courtesy of Benson & Mangold, LLC
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For Sale
$399,000
6416 Edesville Road
Edesville MD 21661
Single-Family
Listing courtesy of Rock Hall Properties Real Estate
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For Sale
$443,900
120 Reeand Ln
Church Hill MD 21623
Single-Family
Listing courtesy of Chesapeake Real Estate Associates, LLC
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For Sale
$565,000
204 Double Creek Road
Chestertown MD 21620
Single-Family
Listing courtesy of Doug Ashley Realtors, LLC
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SoldFeb 3, 2026
$359,000
8833 Georgetown Road
Georgetown MD 21620
Single-Family
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company
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SoldFeb 2, 2026
$2,100,000
10121 Fairlee Road
Chestertown MD 21620
Rural
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company and Unrepresented Buyer Office
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Under Contract
$805,000
114 Piper Ct
Church Hill MD 21623
Single-Family
Listing courtesy of Benson & Mangold, LLC
SoldJan 30, 2026
$325,000
303 Cedar Street
Chestertown MD 21620
Single-Family
Listing courtesy of Select Land & Homes, LLC and Cross Street Realtors LLC
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SoldJan 30, 2026
$379,000
104 Iris Road
Kingstown MD 21620
Single-Family
Listing courtesy of Doug Ashley Realtors, LLC and RE/MAX Executive
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SoldJan 30, 2026
$307,000
6345 Rock Hall Rd
Edesville MD 21661
Single-Family
Listing courtesy of Rock Hall Properties Real Estate and Unrepresented Buyer Office
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SoldJan 30, 2026
$424,000
165 Char Nor Manor Boulevard
Chestertown MD 21620
Single-Family
Listing courtesy of RE/MAX Executive and Long & Foster Real Estate, Inc.
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SoldJan 28, 2026
$392,500
108 Primrose Road
Kingstown MD 21620
Single-Family
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company
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SoldJan 23, 2026
$1,100,000
24028 Cliff Drive Extension
Worton MD 21678
Single-Family
Listing courtesy of Gunther-McClary Real Estate and Unrepresented Buyer Office
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SoldJan 23, 2026
$619,000
217 Austin Ct
Church Hill MD 21623
Single-Family
Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty and Keller Williams Select Realtors
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SoldJan 23, 2026
$325,000
676 Deep Landing Rd
Chestertown MD 21620
Single-Family
Listing courtesy of Cross Street Realtors LLC and Bayside Realty
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SoldJan 20, 2026
$235,000
7521 Pine Avenue
Chestertown MD 21620
Single-Family
Listing courtesy of Chesapeake Real Estate Associates, LLC and Doug Ashley Realtors, LLC
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SoldJan 16, 2026
$240,000
100 Metcalfe Road
Chestertown MD 21620
Townhouse
Listing courtesy of Bayside Realty and Douglas Realty LLC
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SoldJan 16, 2026
$255,000
318 Lincoln Drive
Chestertown MD 21620
Single-Family
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company and Samson Properties of DE, LLC
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SoldJan 16, 2026
$364,000
303 E Campus Ave
Chestertown MD 21620
Single-Family
Listing courtesy of Doug Ashley Realtors, LLC and Coldwell Banker Chesapeake Real Estate Company
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SoldJan 16, 2026
$290,000
107 Malone Avenue
Chestertown MD 21620
Single-Family
Listing courtesy of Douglas Realty LLC and Coldwell Banker Chesapeake Real Estate Company
148 - 168 of 427
Suburbs in Chestertown
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- (619) 566-0008