Homes Recently Sold in Chestertown, MD

580 Homes

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

6 Byford Ct, Chestertown, MD 21620

$749,500
3Bd
3Ba
3,136 Sq Ft

SOLD 04/13/26

206 Camelot Dr, Chestertown, MD 21620

$455,000
4Bd
4Ba
2,186 Sq Ft

SOLD 04/13/26

23055 Old Fairlee Rd, Chestertown, MD 21620

$332,000
3Bd
2Ba
1,628 Sq Ft

SOLD 04/10/26

112 Metcalf Rd, Chestertown, MD 21620

$250,000
3Bd
2Ba
1,280 Sq Ft

SOLD 04/10/26

206 Flyway Ln, Chestertown, MD 21620

$512,500
4Bd
4Ba
3,000 Sq Ft

SOLD 04/08/26

8750 Georgetown Rd, Chestertown, MD 21620

$334,000
3Bd
2Ba
1,900 Sq Ft

SOLD 04/06/26

23110 Old Fairlee Rd, Chestertown, MD 21620

$330,000
3Bd
1Ba
1,805 Sq Ft

SOLD 04/03/26

107 Oak Leaf Dr, Chestertown, MD 21620

$295,000
3Bd
3Ba
1,947 Sq Ft

SOLD 03/31/26

129 Parma Rd, Chestertown, MD 21620

$330,000
3Bd
2Ba
1,170 Sq Ft

SOLD 03/31/26

118 Little Harbor Way #201, Chestertown, MD 21620

$665,000
2Bd
3Ba
1,600 Sq Ft

SOLD 03/30/26

9925 Flatland Rd, Chestertown, MD 21620

$180,000
3Bd
2Ba
1,368 Sq Ft

SOLD 03/27/26

105 Pearl Creek Ln, Chestertown, MD 21620

$459,000
3Bd
3Ba
1,961 Sq Ft

SOLD 03/27/26

10751 Millbrook Dr, Chestertown, MD 21620

$350,000
3Bd
2Ba
1,942 Sq Ft

SOLD 03/27/26

Elm Road, Chestertown, MD 21620

$13,000
0.09 Acre

SOLD 03/24/26

Elm Road, Chestertown, MD 21620

$35,000
0.33 Acre

SOLD 03/20/26

204 Rolling Rd, Chestertown, MD 21620

$340,000
3Bd
2Ba
2,296 Sq Ft

SOLD 03/19/26

119 Darden Rd, Chestertown, MD 21620

$270,000
3Bd
2Ba
1,424 Sq Ft

SOLD 03/18/26

121 Primrose Rd, Chestertown, MD 21620

$325,000
3Bd
3Ba
2,034 Sq Ft

SOLD 03/18/26

200 Washington Ave, Chestertown, MD 21620

$650,000
4Bd
4Ba
2,917 Sq Ft

SOLD 03/10/26

23069 Raleigh Rd, Chestertown, MD 21620

$175,000
2Bd
—Ba
1,160 Sq Ft

SOLD 03/10/26

213 Central Dr, Chestertown, MD 21620

$317,000
3Bd
2Ba
1,232 Sq Ft

SOLD 03/09/26

21111 Texas Ave, Chestertown, MD 21620

$350,000
3Bd
2Ba
1,680 Sq Ft

SOLD 03/05/26

Hoffecker Road, Chestertown, MD 21620

$190,000
10.05 Acre

SOLD 03/04/26

423 Calvert St, Chestertown, MD 21620

$125,000
3Bd
2Ba
1,136 Sq Ft

SOLD 03/02/26

109 Water St, Chestertown, MD 21620

$650,000
4Bd
2Ba
2,064 Sq Ft

SOLD 02/27/26

141 Prospect St, Chestertown, MD 21620

$120,000
4Bd
2Ba
1,156 Sq Ft

SOLD 02/27/26

108 Flying Cloud Dr, Chestertown, MD 21620

$364,900
4Bd
3Ba
1,936 Sq Ft

SOLD 02/26/26

4671 Cliffs City Rd, Chestertown, MD 21620

$800,000
3Bd
2Ba
1,783 Sq Ft

SOLD 02/20/26

24339 Chestertown Rd, Chestertown, MD 21620

$270,000
3Bd
1Ba
960 Sq Ft

SOLD 02/19/26

Caulks Field Road, Chestertown, MD 21620

$11,000
2 Acre

SOLD 02/19/26

134 Char Nor Manor Blvd, Chestertown, MD 21620

$260,000
3Bd
1Ba
1,128 Sq Ft

SOLD 02/18/26

10800 Cliff Rd, Chestertown, MD 21620

$1,524,900
5Bd
4Ba
5,241 Sq Ft

SOLD 02/17/26

21316 Persimmon Dr, Chestertown, MD 21620

$160,000
2Bd
1Ba
1,232 Sq Ft

SOLD 02/13/26

8833 Georgetown Rd, Chestertown, MD 21620

$359,000
4Bd
2Ba
1,625 Sq Ft

SOLD 02/03/26

1 - 50 of 580 Homes in Chestertown, MD

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Chestertown, MD Real Estate Snapshot

List Price

$399,900

$/Sqft

$247

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Home Size

1,865 Sqft

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