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Chestertown
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Real Estate & Property for Sale in
Chestertown
Showing 148 - 168 of 428 properties
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Michael ONeill
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For Sale
$549,000
1271212714 Still Pond Road
Still Pond MD 21667
5
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2
Duplex
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company
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Sold
May 19, 2026
$376,000
136 Hilltop Drive
Chestertown MD 21620
3
2
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5
Single-Family
Listing courtesy of Northrop Realty and Long & Foster Real Estate, Inc.
Erin Anderson
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Under Contract
$365,000
240 Merganser Drive
Chestertown MD 21620
3
2
Single-Family
Listing courtesy of Chesapeake Real Estate Associates, LLC
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Sold
May 18, 2026
$90,000
Big Woods Rd
Church Hill MD 21623
Land
Listing courtesy of Keller Williams Select Realtors and National Land Realty, LLC
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Sold
May 18, 2026
$259,900
107 Metcalfe Road
Chestertown MD 21620
3
2
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1
Townhouse
Listing courtesy of Real Broker, LLC and Coldwell Banker Chesapeake Real Estate Company
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Sold
May 18, 2026
$695,000
10087 John Carvill Road
Chestertown MD 21620
3
2
Single-Family
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company and REMAX Chesapeake | Elkton
Cynthia Gardner
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Under Contract
$375,000
107 Flying Cloud Drive
Chestertown MD 21620
5
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Single-Family
Listing courtesy of CENTURY 21 New Millennium
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Sold
May 15, 2026
$15,000
23698 L Road
Chestertown MD 21620
Land
Listing courtesy of Taylor Properties and Unrepresented Buyer Office
Sold
May 15, 2026
$280,000
111 Cemetery Lane
Church Hill MD 21623
3
1
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Single-Family
Listing courtesy of Clark & Co Realty, LLC and Rosendale Realty
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Sold
May 15, 2026
$150,000
107 Conley Drive
Chestertown MD 21620
3
1
Townhouse
Listing courtesy of Doug Ashley Realtors, LLC and Benson & Mangold, LLC
John Carroll
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For Sale
$49,000
Sandy Bottom Rd
Chestertown MD 21620
Land
Listing courtesy of Village Real Estate Company LLC
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Sold
May 14, 2026
$278,500
107 Longfellow Drive
Kingstown MD 21620
3
1
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4
Single-Family
Listing courtesy of Doug Ashley Realtors, LLC and Lofgren-Sargent Real Estate
Mae Nordhoff
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Pending
$59,999
228 Merganser Drive
Chestertown MD 21620
Land
Listing courtesy of Benson & Mangold, LLC
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Sold
May 13, 2026
$155,000
132 Prospect Street
Chestertown MD 21620
2
1
Single-Family
Listing courtesy of ANR Realty, LLC and Long & Foster Real Estate, Inc.
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Sold
May 11, 2026
$399,900
1824 Price Station Road
Church Hill MD 21623
3
2
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2
Single-Family
Listing courtesy of Redfin Corp and Coldwell Banker Chesapeake Real Estate Company
Kaitlin Stecklair
For Sale
$135,000
109 2nd Street
Chestertown MD 21620
Land
Listing courtesy of Cross Street Realtors LLC
Sold
May 8, 2026
$362,500
115 Cemetery Lane
Church Hill MD 21623
3
2
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3
Single-Family
Listing courtesy of Redfin Corp and Benson & Mangold, LLC
Richard Keaveney
Sold
May 8, 2026
$4,200,000
29048 Belchester Road
Kennedyville MD 21645
1
2
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Single-Family
Listing courtesy of Cross Street Realtors LLC
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Sold
May 8, 2026
$490,000
100 Adela Way
Chestertown MD 21620
4
4
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2
Single-Family
Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty and Keller Williams Gateway LLC
Sold
May 8, 2026
$221,450
602 Main Street
Church Hill MD 21623
3
2
Single-Family
Listing courtesy of LPT Realty, LLC and Unrepresented Buyer Office
Richard Keaveney
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Sold
May 8, 2026
$750,000
29030 Belchester Rd
Kennedyville MD 21645
5
3
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2
Single-Family
Listing courtesy of Cross Street Realtors LLC
148 - 168 of 428
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Suburbs in Chestertown
21620
View nearby Cities
Kingstown
Worton
Butlertown
Fairlee
Georgetown
Church Hill
Kennedyville
Still Pond
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Edesville
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