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Real Estate & Property for Sale in Chestertown

Showing 1 - 21 of 290 properties
SoldOct 27, 2026
$329,900
10725 Worton Road
Worton MD 21678
2
2
Single-Family
Listing courtesy of Select Land & Homes, LLC and Patterson-Schwartz Real Estate | Middletown Office
SoldOct 27, 2026
$665,000
7712 Waterview Lane
Chestertown MD 21620
3
4
6
Single-Family
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company
SoldOct 27, 2026
$240,000
11060 Plum Drive
Butlertown MD 21678
3
1
Single-Family
Listing courtesy of Patterson-Schwartz Real Estate | Newark Office and Keller Williams Realty 42
SoldOct 26, 2026
$545,000
204 South Front Street
Chestertown MD 21620
2
2
Single-Family
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company and Sharon Real Estate P.C.
SoldOct 23, 2026
$664,000
478 Eagle Manor Drive
Church Hill MD 21623
4
3
2
Single-Family
Listing courtesy of CR Realty and Pearson Smith Realty, LLC
SoldOct 22, 2026
$650,000
209 Shoals Road
Crumpton MD 21628
3
3
Single-Family
Listing courtesy of Doug Ashley Realtors, LLC
SoldOct 22, 2026
$300,000
7464 Shortall St
Chestertown MD 21620
3
2
2
Single-Family
Listing courtesy of Chesapeake Real Estate Associates, LLC and Benson & Mangold, LLC
SoldOct 21, 2026
$325,000
109 Parma Road
Kingstown MD 21620
3
2
4
Single-Family
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company and Coldwell Banker Realty
SoldOct 19, 2026
SoldOct 16, 2026
$525,000
204 Double Creek Road
Chestertown MD 21620
3
3
4
Single-Family
Listing courtesy of Doug Ashley Realtors, LLC
SoldOct 15, 2026
$3,000
Sandpiper Road
Chestertown MD 21620
Land
Listing courtesy of Chesapeake Real Estate Associates, LLC and Realty One Group Capital Properties
SoldOct 7, 2026
$261,000
3C/116 The Pond Way
Church Hill MD 21623
2
2
1
Condo
Listing courtesy of Coldwell Banker Waterman Realty and Douglas Realty LLC
SoldOct 5, 2026
$1,050,000
26230 Royal Swan Road
Still Pond MD 21667
3
4
2
Rural
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company and Heroes Real Estate
SoldSep 30, 2026
$450,000
25750 Collins Avenue
Chestertown MD 21620
3
2
6
Single-Family
Listing courtesy of Doug Ashley Realtors, LLC and Coldwell Banker Chesapeake Real Estate Company
SoldSep 30, 2026
$290,000
522 High Street
Chestertown MD 21620
2
3
Single-Family
Listing courtesy of Benson & Mangold, LLC and CR Realty
SoldSep 29, 2026
$295,000
240 Round Top Road
Chestertown MD 21620
3
2
Single-Family
Listing courtesy of Clark & Co Realty, LLC and Long & Foster Real Estate, Inc.
SoldSep 28, 2026
$495,000
218 Camelot Drive
Chestertown MD 21620
5
4
6
Single-Family
Listing courtesy of Coldwell Banker Realty and Samson Properties
SoldSep 22, 2026
$349,000
123 Heath Road
Kingstown MD 21620
3
2
2
Single-Family
Listing courtesy of Chesapeake Real Estate Associates, LLC
SoldSep 22, 2026
$260,000
249 Island Lark Way
Chestertown MD 21620
3
3
Townhouse
Listing courtesy of Cross Street Realtors LLC
SoldSep 18, 2026
$332,000
11035 Bottom Road
Butlertown MD 21678
3
2
Single-Family
Listing courtesy of Keller Williams Select Realtors and Coldwell Banker Realty
SoldSep 18, 2026
$445,000
104 Church Alley
Chestertown MD 21620
2
2
Townhouse
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company and Unrepresented Buyer Office
1 - 21 of 290

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