Homes Recently Sold in 21690, MD

363 Homes

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

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

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

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

103 Flying Cloud Dr, Chestertown, MD 21620

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

SOLD 04/21/26

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

201 Greenwood Ave, Chestertown, MD 21620

$495,000
4Bd
3Ba
3,984 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

112 Metcalf Rd, Chestertown, MD 21620

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

SOLD 04/10/26

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

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

213 Central Dr, Chestertown, MD 21620

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

SOLD 03/09/26

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

104 Iris Rd, Chestertown, MD 21620

$379,000
3Bd
2Ba
1,700 Sq Ft

SOLD 01/30/26

303 Cedar St, Chestertown, MD 21620

$325,000
3Bd
3Ba
2,577 Sq Ft

SOLD 01/30/26

108 Primrose Rd, Chestertown, MD 21620

$392,500
3Bd
2Ba
1,722 Sq Ft

SOLD 01/28/26

112 Silver Heel Dr, Chestertown, MD 21620

$379,900
5Bd
4Ba
2,615 Sq Ft

SOLD 01/21/26

7521 Pine Ave, Chestertown, MD 21620

$235,000
3Bd
1Ba
1,040 Sq Ft

SOLD 01/20/26

318 Lincoln, Chestertown, MD 21620

$255,000
3Bd
2Ba
960 Sq Ft

SOLD 01/16/26

107 Malone Ave, Chestertown, MD 21620

$290,000
3Bd
1Ba
1,200 Sq Ft

SOLD 01/16/26

100 Metcalf Rd, Chestertown, MD 21620

$240,000
3Bd
2Ba
1,140 Sq Ft

SOLD 01/16/26

206 Cannon St, Chestertown, MD 21620

$800,000
1.56 Acre

SOLD 01/15/26

206 Valley, Chestertown, MD 21620

$590,000
4Bd
2Ba
2,869 Sq Ft

SOLD 01/12/26

26933 Mallard Rd, Chestertown, MD 21620

$555,000
3Bd
3Ba
1,600 Sq Ft

SOLD 01/12/26

411 Greenwood Ave, Chestertown, MD 21620

$415,000
3Bd
3Ba
1,676 Sq Ft

SOLD 01/07/26

492 Pear Tree Point Rd, Chestertown, MD 21620

$850,000
3Bd
2Ba
3,720 Sq Ft

SOLD 12/19/25

517 High St, Chestertown, MD 21620

$361,500
—Bd
—Ba
1,728 Sq Ft

SOLD 12/19/25

25195 Lovers Ln, Chestertown, MD 21620

$350,000
1Bd
1Ba
1,002 Sq Ft

SOLD 12/15/25

101 Birch Run Rd, Chestertown, MD 21620

$475,000
3Bd
2Ba
1,961 Sq Ft

SOLD 12/11/25

101 Metcalf Rd, Chestertown, MD 21620

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

SOLD 12/05/25

302 Rosin Dr, Chestertown, MD 21620

$550,000
5Bd
4Ba
3,877 Sq Ft

SOLD 12/05/25

600 Rosin Dr, Chestertown, MD 21620

$413,300
3Bd
2Ba
1,300 Sq Ft

SOLD 12/05/25

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