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Real Estate & Property for Sale in Chestertown

Showing 190 - 210 of 428 properties
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SoldDec 24, 2025
$294,000
25135 Smithville Road
Butlertown MD 21678
3
1
2
Single-Family
Listing courtesy of RE/MAX Advantage Realty and Coldwell Banker Chesapeake Real Estate
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SoldDec 22, 2025
$80,000
5700 Johnsontown Road
Chestertown MD 21620
3
1
Single-Family
Listing courtesy of Tesla Realty Group, LLC and Coldwell Banker Chesapeake Real Estate
Jordan Larigan Jordan Larigan
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SoldDec 22, 2025
$120,000
1040 Price Station Road
Church Hill MD 21623
4
2
Single-Family
Listing courtesy of Vybe Realty
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SoldDec 19, 2025
$361,500
517 High Street
Chestertown MD 21620
3
Duplex
Listing courtesy of L. C. Parker Real Estate and Select Land & Homes, LLC
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SoldDec 19, 2025
$850,000
492 Pear Tree Point Road
Chestertown MD 21620
3
2
2
Single-Family
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company and Benson & Mangold, LLC
SoldDec 15, 2025
$350,000
25195 Lovers Lane
Chestertown MD 21620
1
1
Single-Family
Listing courtesy of Select Land & Homes, LLC and Unrepresented Buyer Office
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SoldDec 11, 2025
$542,000
272 Granny Branch Road
Church Hill MD 21623
5
4
5
Single-Family
Listing courtesy of Coldwell Banker Realty and eXp Realty, LLC (E - SR12 - Maryland)
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SoldDec 11, 2025
$475,000
101 Birch Run Road
Chestertown MD 21620
3
2
2
Single-Family
Listing courtesy of Remax Vision and RE/MAX Real Estate Connections
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SoldDec 10, 2025
$1,150,000
23393 Cacaway Farm Lane
Chestertown MD 21620
3
4
2
Other
Listing courtesy of Gunther-McClary Real Estate and Rock Hall Properties Real Estate
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SoldDec 9, 2025
$355,000
10740 Worton Road
Worton MD 21678
3
3
3
Single-Family
Listing courtesy of Doug Ashley Realtors, LLC and Cross Street Realtors LLC
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SoldDec 8, 2025
$75,000
109 2nd Street
Chestertown MD 21620
Land
Listing courtesy of Ashland Auction Group LLC and Unrepresented Buyer Office
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SoldDec 5, 2025
$550,000
302 Rosin Drive
Kingstown MD 21620
5
4
6
Single-Family
Listing courtesy of Cross Street Realtors LLC
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SoldDec 5, 2025
$349,900
26994 Branchtown Road
Worton MD 21678
4
2
Single-Family
Listing courtesy of Kevin Dey Realty and Chesapeake Real Estate Associates, LLC
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SoldDec 5, 2025
$287,500
7483 Shortall Street
Chestertown MD 21620
3
2
Single-Family
Listing courtesy of RE/MAX Executive and ExecuHome Realty
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SoldDec 5, 2025
$264,900
101 Metcalfe Road
Chestertown MD 21620
3
2
1
Townhouse
Listing courtesy of Real Broker, LLC and Chesapeake Real Estate Associates, LLC
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SoldDec 5, 2025
$413,300
600 Rosin Drive
Kingstown MD 21620
3
2
Single-Family
Listing courtesy of Doug Ashley Realtors, LLC
Julia Hilfiker Julia Hilfiker
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For Sale
$765,900
37 Landing Lane
Chestertown MD 21620
3
3
2
Condo
Listing courtesy of Gunther-McClary Real Estate
John Burke John Burke
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For Sale
$753,500
36 Landing Lane
Chestertown MD 21620
3
3
2
Condo
Listing courtesy of Gunther-McClary Real Estate
Julia Hilfiker Julia Hilfiker
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For Sale
$786,900
35 Landing Lane
Chestertown MD 21620
3
3
2
Condo
Listing courtesy of Gunther-McClary Real Estate
John Burke John Burke
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For Sale
$813,900
104 Landing Lane
Chestertown MD 21620
3
4
2
Condo
Listing courtesy of Gunther-McClary Real Estate
John Burke John Burke
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For Sale
$839,500
102 Little Harbor Way
Chestertown MD 21620
3
3
2
Condo
Listing courtesy of Gunther-McClary Real Estate
190 - 210 of 428

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