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Real Estate & Property for Sale in Chestertown

Showing 22 - 42 of 424 properties
John Carroll John Carroll
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For Sale
$79,000
Sandy Bottom Rd
Chestertown MD 21620
Land
Listing courtesy of Village Real Estate Company LLC
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SoldMay 14, 2026
$278,500
107 Longfellow Drive
Kingstown MD 21620
3
1
4
Single-Family
Listing courtesy of Doug Ashley Realtors, LLC and Lofgren-Sargent Real Estate
Maryn LeClair Maryn LeClair
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For Sale
$75,000
11200 Boyer Lane
Worton MD 21678
Land
Listing courtesy of Chesapeake Real Estate Associates, LLC
Mae Nordhoff Mae Nordhoff
For Sale
$99,000
228 Merganser Drive
Chestertown MD 21620
Land
Listing courtesy of Benson & Mangold, LLC
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SoldMay 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.
Liddy Campbell Liddy Campbell
Under Contract
$325,000
202 Valley Rd
Chestertown MD 21620
3
1
1
Single-Family
Listing courtesy of TTR Sotheby's International Realty
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SoldMay 11, 2026
$399,900
1824 Price Station Road
Church Hill MD 21623
3
2
2
Single-Family
Listing courtesy of Redfin Corp and Coldwell Banker Chesapeake Real Estate Company
Kaitlin Stecklair Kaitlin Stecklair
For Sale
$150,000
109 2nd Street
Chestertown MD 21620
Land
Listing courtesy of Cross Street Realtors LLC
Harmony Campbell Harmony Campbell
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Under Contract
$415,000
12089 Blacks Station Road
Kennedyville MD 21645
4
2
2
Single-Family
Listing courtesy of Coldwell Banker Realty
SoldMay 8, 2026
$362,500
115 Cemetery Lane
Church Hill MD 21623
3
2
3
Single-Family
Listing courtesy of Redfin Corp and Benson & Mangold, LLC
Richard Keaveney Richard Keaveney
SoldMay 8, 2026
$4,200,000
29048 Belchester Road
Kennedyville MD 21645
1
2
6
Single-Family
Listing courtesy of Cross Street Realtors LLC
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SoldMay 8, 2026
$490,000
100 Adela Way
Chestertown MD 21620
4
4
2
Single-Family
Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty and Keller Williams Gateway LLC
SoldMay 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 Richard Keaveney
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SoldMay 8, 2026
$750,000
29030 Belchester Rd
Kennedyville MD 21645
5
3
2
Single-Family
Listing courtesy of Cross Street Realtors LLC
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SoldMay 8, 2026
$1,050,000
25209 Wymont Park Road
Worton MD 21678
3
1
4
Single-Family
Listing courtesy of Doug Ashley Realtors, LLC and KELLER WILLIAMS LEGACY
Warren Hogan Warren Hogan
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Pending
$535,000
9816 Fairlee Road
Chestertown MD 21620
3
3
Single-Family
Listing courtesy of Long & Foster Real Estate, Inc.
Michele Palmer Michele Palmer
5
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For Sale
$179,000
144 Prospect Street
Chestertown MD 21620
2
2
2
Single-Family
Listing courtesy of Doug Ashley Realtors, LLC
Mary Julie Mary Julie
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Under Contract
$425,000
215 Fairview Drive
Kingstown MD 21620
3
3
4
Single-Family
Listing courtesy of Long & Foster Real Estate, Inc.
Lisa Raffetto Lisa Raffetto
5
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For Sale
$828,000
407 High Street
Chestertown MD 21620
3
5
2
Single-Family
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company
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SoldMay 6, 2026
$75,000
116 2nd Street
Crumpton MD 21628
Land
Listing courtesy of Coldwell Banker Realty and Chesapeake Real Estate Associates, LLC
SoldMay 4, 2026
$480,000
101 Pine Tree Road
Chestertown MD 21620
4
2
2
Single-Family
Listing courtesy of Rosendale Realty and RE/MAX Executive
22 - 42 of 424

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