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Real Estate & Property for Sale in Chestertown
Most Recent
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SoldNov 7, 2025
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For Sale
$322,500
304 Hadaway Drive
Chestertown MD 21620
Single-Family
Listing courtesy of Redfin Corporation
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For Sale
$429,999
222 Mt Vernon Avenue
Chestertown MD 21620
Single-Family
Listing courtesy of Long & Foster Real Estate, Inc.
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For Sale
$289,900
545/545 High Street
Chestertown MD 21620
Townhouse
Listing courtesy of Select Land & Homes, LLC
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SoldNov 5, 2025
$535,000
5179 Quaker Neck Rd
Chestertown MD 21620
Single-Family
Listing courtesy of Hyatt & Company Real Estate, LLC and KELLER WILLIAMS LEGACY
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SoldNov 5, 2025
$695,000
110 S Mill St
Chestertown MD 21620
Single-Family
Listing courtesy of Gunther-McClary Real Estate and Cross Street Realtors LLC
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SoldNov 3, 2025
$435,000
25800 Collins Ave
Chestertown MD 21620
Single-Family
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company and NORTHROP REALTY
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SoldOct 31, 2025
$60,000
Station Rd
Worton MD 21678
Land
Listing courtesy of Doug Ashley Realtors, LLC and RE/MAX Chesapeake
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SoldOct 31, 2025
$560,000
136 Truslow Farm Lane
Kingstown MD 21620
Land
Listing courtesy of Chesapeake Real Estate Associates, LLC and Coldwell Banker Chesapeake Real Estate Company
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SoldOct 31, 2025
$485,960
726 Aldora Drive
Chestertown MD 21620
Townhouse
Listing courtesy of Builder Solutions Realty and Vybe Realty
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SoldOct 30, 2025
$520,000
11307 Urieville Lane
Worton MD 21678
Single-Family
Listing courtesy of RE/MAX Executive and Select Land & Homes, LLC
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SoldOct 30, 2025
$250,000
2101 Dudley Corners Road
Crumpton MD 21628
Single-Family
Listing courtesy of Benson & Mangold, LLC and Rock Hall Properties Real Estate
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SoldOct 30, 2025
$319,500
29380 Old Locust Grove Rd
Kennedyville MD 21645
Single-Family
Listing courtesy of Select Land & Homes, LLC and Coldwell Banker Chesapeake Real Estate Company
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SoldOct 30, 2025
$392,500
128 Edmore Road
Kingstown MD 21620
Single-Family
Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty and Long & Foster Real Estate, Inc.
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SoldOct 30, 2025
$264,900
24415 Chestertown Rd
Chestertown MD 21620
Single-Family
Listing courtesy of TTR Sotheby's International Realty and Remax Vision
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SoldOct 28, 2025
$130,000
334 Eagle Manor Drive
Church Hill MD 21623
Land
Listing courtesy of Chesapeake Real Estate Associates, LLC and Long & Foster Real Estate, Inc.
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SoldOct 27, 2025
$620,000
7729 Country Club Ln
Chestertown MD 21620
Single-Family
Listing courtesy of Cross Street Realtors LLC and Vybe Realty
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For Sale
$419,900
109 South College Avenue
Chestertown MD 21620
Single-Family
Listing courtesy of Taylor Properties
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SoldOct 24, 2025
$398,000
221 Richard Drive
Chestertown MD 21620
Single-Family
Listing courtesy of TTR Sotheby's International Realty
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For Sale
$670,000
7844 Chester Ct
Chestertown MD 21620
Single-Family
Listing courtesy of Doug Ashley Realtors, LLC
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SoldOct 22, 2025
$2,000,000
12530 Dads Desire Lane
Worton MD 21678
Single-Family
Listing courtesy of Compass and Unrepresented Buyer Office
253 - 273 of 426
Suburbs in Chestertown
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- (619) 566-0008