Homes Recently Sold in Chestertown, MD

582 Homes

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

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

21324 Persimmon Dr, Chestertown, MD 21620

$112,500
2Bd
1Ba
1,232 Sq Ft

SOLD 06/09/26

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

10594 Millbrook Dr, Chestertown, MD 21620

$329,000
3Bd
2Ba
1,499 Sq Ft

SOLD 05/27/26

154 Longfellow Dr, Chestertown, MD 21620

$300,000
3Bd
1Ba
1,408 Sq Ft

SOLD 05/27/26

25475 Turnberry Ct, Chestertown, MD 21620

$825,000
4Bd
4Ba
4,145 Sq Ft

SOLD 05/26/26

109 Metcalf Rd, Chestertown, MD 21620

$264,900
3Bd
2Ba
1,280 Sq Ft

SOLD 05/26/26

349 351 High St, Chestertown, MD 21620

$355,000
—Bd
—Ba
3,664 Sq Ft

SOLD 05/26/26

108 Oak Leaf Dr, Chestertown, MD 21620

$296,500
2Bd
3Ba
1,867 Sq Ft

SOLD 05/22/26

136 Hilltop Dr, Chestertown, MD 21620

$376,000
3Bd
2Ba
1,432 Sq Ft

SOLD 05/19/26

10087 John Carvill Rd, Chestertown, MD 21620

$695,000
3Bd
2Ba
1,566 Sq Ft

SOLD 05/18/26

107 Metcalf Rd, Chestertown, MD 21620

$259,900
3Bd
2Ba
1,200 Sq Ft

SOLD 05/18/26

107 Conley Dr, Chestertown, MD 21620

$150,000
3Bd
1Ba
1,140 Sq Ft

SOLD 05/15/26

23698 L Rd, Chestertown, MD 21620

$15,000
2.6 Acre

SOLD 05/15/26

107 Longfellow Dr, Chestertown, MD 21620

$278,500
3Bd
1Ba

SOLD 05/14/26

132 Prospect St, Chestertown, MD 21620

$155,000
2Bd
1Ba
910 Sq Ft

SOLD 05/13/26

100 Adela Way, Chestertown, MD 21620

$490,000
4Bd
4Ba
3,799 Sq Ft

SOLD 05/08/26

101 Pine Tree Rd, Chestertown, MD 21620

$480,000
4Bd
2Ba
1,848 Sq Ft

SOLD 05/04/26

217 Philosophers Ter, Chestertown, MD 21620

$370,000
3Bd
2Ba
1,404 Sq Ft

SOLD 05/01/26

206 S Water St, Chestertown, MD 21620

$545,000
4Bd
3Ba
2,008 Sq Ft

SOLD 04/30/26

144 Char Nor Manor Blvd, Chestertown, MD 21620

$50,000
0.52 Acre

SOLD 04/29/26

103 Flying Cloud Dr, Chestertown, MD 21620

$339,900
3Bd
3Ba
1,724 Sq Ft

SOLD 04/21/26

11040 Kylie Ln, Chestertown, MD 21620

$620,000
4Bd
4Ba
3,684 Sq Ft

SOLD 04/20/26

515 N Kent St, Chestertown, MD 21620

$495,000
4Bd
3Ba
2,220 Sq Ft

SOLD 04/17/26

104 Garland Ave, Chestertown, MD 21620

$480,000
3Bd
2Ba
1,734 Sq Ft

SOLD 04/17/26

148 Step Rd, Chestertown, MD 21620

$365,000
4Bd
2Ba
1,400 Sq Ft

SOLD 04/17/26

201 Greenwood Ave, Chestertown, MD 21620

$495,000
4Bd
3Ba
3,984 Sq Ft

SOLD 04/17/26

216 Blakefield Dr, Chestertown, MD 21620

$552,000
4Bd
3Ba
2,400 Sq Ft

SOLD 04/17/26

513 Round Top Rd, Chestertown, MD 21620

$220,000
4Bd
1Ba
1,248 Sq Ft

SOLD 04/14/26

1 - 50 of 582 Homes in Chestertown, MD

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Chestertown, MD Real Estate Snapshot

List Price

$407,450

$/Sqft

$247

Homes For Sale

Home Size

1,864 Sqft

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