Homes Recently Sold in Chestertown, MD

581 Homes

109 Cedar St, Chestertown, MD 21620

$318,000
3Bd
3Ba
1,397 Sq Ft

SOLD 08/14/26

202 Royston Shores Rd, Chestertown, MD 21620

$1,200,000
4Bd
3Ba
2,292 Sq Ft

SOLD 08/14/26

25440 Learman Rd, Chestertown, MD 21620

$3,000,000
3Bd
4Ba
3,142 Sq Ft

SOLD 08/14/26

102 Flying Cloud Dr, Chestertown, MD 21620

$324,000
3Bd
3Ba
1,896 Sq Ft

SOLD 08/14/26

7989 Quaker Neck Rd, Chestertown, MD 21620

$1,900,000
5Bd
5Ba
4,305 Sq Ft

SOLD 08/14/26

116 Cross St, Chestertown, MD 21620

$104,000
0.18 Acre

SOLD 08/13/26

East Street, Chestertown, MD 21620

$75,000
0.48 Acre

SOLD 08/13/26

1904 Pondtown Rd, Chestertown, MD 21620

$247,500
3Bd
1Ba
1,967 Sq Ft

SOLD 08/10/26

139 Prospect St, Chestertown, MD 21620

$195,000
3Bd
1Ba
1,200 Sq Ft

SOLD 07/31/26

304 Hadaway Dr, Chestertown, MD 21620

$300,000
4Bd
2Ba
1,325 Sq Ft

SOLD 07/30/26

7844 Chester Ct, Chestertown, MD 21620

$640,000
4Bd
3Ba
3,248 Sq Ft

SOLD 07/29/26

21217 Texas Ave, Chestertown, MD 21620

$244,000
2Bd
1Ba
912 Sq Ft

SOLD 07/27/26

521 N Kent St, Chestertown, MD 21620

$365,000
3Bd
2Ba
1,934 Sq Ft

SOLD 07/22/26

100 Prospect St, Chestertown, MD 21620

$215,000
3Bd
1Ba
1,373 Sq Ft

SOLD 07/21/26

10572 Watonga Rd, Chestertown, MD 21620

$325,000
3Bd
2Ba
1,404 Sq Ft

SOLD 07/16/26

215 Fairview Dr, Chestertown, MD 21620

$435,000
3Bd
3Ba
1,784 Sq Ft

SOLD 07/16/26

704 Truslow Rd, Chestertown, MD 21620

$453,000
3Bd
3Ba
2,060 Sq Ft

SOLD 07/14/26

221 Dutchess Rd, Chestertown, MD 21620

$228,000
3Bd
2Ba
2,260 Sq Ft

SOLD 07/13/26

23264 Clarissa Rd, Chestertown, MD 21620

$365,000
3Bd
2Ba
1,248 Sq Ft

SOLD 07/13/26

110 S Queen St, Chestertown, MD 21620

$541,500
3Bd
2Ba
1,785 Sq Ft

SOLD 07/10/26

9816 Fairlee Rd, Chestertown, MD 21620

$535,000
3Bd
3Ba
1,624 Sq Ft

SOLD 07/10/26

10584 Klamath Rd, Chestertown, MD 21620

$320,000
3Bd
2Ba

SOLD 07/08/26

206 Burchard Sawmill Rd, Chestertown, MD 21620

$9,000
1.05 Acre

SOLD 07/08/26

144 Prospect St, Chestertown, MD 21620

$165,000
2Bd
2Ba
1,082 Sq Ft

SOLD 07/07/26

21363 Lynn Ln, Chestertown, MD 21620

$205,000
3Bd
1Ba
1,314 Sq Ft

SOLD 07/02/26

114 Chester Vw, Chestertown, MD 21620

$1,650,000
3Bd
2Ba
2,064 Sq Ft

SOLD 06/30/26

108 Pine St, Chestertown, MD 21620

$85,000
3Bd
1Ba
910 Sq Ft

SOLD 06/30/26

118 Grant Ct, Chestertown, MD 21620

$460,000
3Bd
2Ba
1,664 Sq Ft

SOLD 06/29/26

7761 Broad Neck Rd, Chestertown, MD 21620

$1,550,000
5Bd
3Ba
2,700 Sq Ft

SOLD 06/29/26

23416 Cloquet Rd, Chestertown, MD 21620

$384,000
3Bd
2Ba
1,512 Sq Ft

SOLD 06/29/26

1014 Twin Ct, Chestertown, MD 21620

$525,000
3Bd
2Ba
1,817 Sq Ft

SOLD 06/26/26

423 Calvert St, Chestertown, MD 21620

$190,000
3Bd
2Ba
1,136 Sq Ft

SOLD 06/26/26

109 S College Ave, Chestertown, MD 21620

$410,000
3Bd
3Ba
1,216 Sq Ft

SOLD 06/26/26

231 Richard Dr, Chestertown, MD 21620

$1,050,000
5Bd
3Ba
2,956 Sq Ft

SOLD 06/26/26

8629 Airy Hill Rd, Chestertown, MD 21620

$395,000
3Bd
2Ba
1,440 Sq Ft

SOLD 06/25/26

205 River Rd, Chestertown, MD 21620

$855,000
4Bd
3Ba
2,877 Sq Ft

SOLD 06/24/26

202 Valley Rd, Chestertown, MD 21620

$325,000
3Bd
1Ba
1,427 Sq Ft

SOLD 06/17/26

127 Wood Duck Ln, Chestertown, MD 21620

$135,000
3Bd
2Ba
1,666 Sq Ft

SOLD 06/12/26

720 Deep Landing Rd, Chestertown, MD 21620

$360,000
3Bd
2Ba
1,271 Sq Ft

SOLD 06/12/26

112 Elm St, Chestertown, MD 21620

$249,000
3Bd
1Ba
1,356 Sq Ft

SOLD 06/12/26

301 Lincoln Dr, Chestertown, MD 21620

$293,000
3Bd
2Ba
1,152 Sq Ft

SOLD 06/08/26

126 Char Nor Manor Blvd, Chestertown, MD 21620

$349,500
3Bd
2Ba
1,304 Sq Ft

SOLD 06/05/26

21125 Iowa Ave, Chestertown, MD 21620

$339,900
2Bd
1Ba
1,294 Sq Ft

SOLD 06/05/26

113 Pear Tree Point Rd, Chestertown, MD 21620

$175,000
3Bd
1Ba
1,296 Sq Ft

SOLD 06/05/26

118 Little Harbor Way #202, Chestertown, MD 21620

$660,000
3Bd
2Ba
1,600 Sq Ft

SOLD 06/05/26

115 Acorn Dr, Chestertown, MD 21620

$290,000
2Bd
3Ba
1,864 Sq Ft

SOLD 06/04/26

lot S 253-254 Carimon Rd, Chestertown, MD 21620

$7,200
0.34 Acre

SOLD 06/04/26

22360 Great Oak Landing Rd, Chestertown, MD 21620

$525,000
5Bd
4Ba
2,688 Sq Ft

SOLD 05/29/26

2032 Pondtown Rd, Chestertown, MD 21620

$365,000
3Bd
2Ba
1,120 Sq Ft

SOLD 05/29/26

201 Birch Run Rd, Chestertown, MD 21620

$430,000
3Bd
2Ba
1,588 Sq Ft

SOLD 05/29/26

1 - 50 of 581 Homes in Chestertown, MD

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Chestertown, MD Real Estate Snapshot

List Price

$402,499

$/Sqft

$240

Homes For Sale

Home Size

1,980 Sqft

Days on Movoto

100

Frequently Asked Questions about Real Estate in Chestertown, MD

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Movoto gives you access to up-to-the-minute information about real estate in Chestertown. As a licensed brokerage in Maryland (and across the United States), Movoto has access to the latest real estate data including Chestertown Homes for Sale, Chestertown Single family for Sale, Chestertown Townhomes/Condos for Sale, Chestertown Multi family/Duplex for Sale, Chestertown Land for Sale, Chestertown New Listings for Sale, Chestertown Rentals, Chestertown Apartments for Rent, Chestertown Single Family for Rent, Chestertown Waterfront for Sale, Chestertown Foreclosures for Sale.

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