Recently sold homes in Chestertown, MD

smover Index for Chestertown: 45 / 100: how it is measured

60 homes sold in Chestertown, MD in the last year. Each links to its full sale record — price, photos, and details.

$435,000Sold Jul 2026

215 FAIRVIEW DRIVE

Chestertown, MD 21620

3 bd · 3 ba · 1,784 sqft

$453,000Sold Jul 2026

704 TRUSLOW ROAD

Chestertown, MD 21620

3 bd · 3 ba · 2,060 sqft

$228,000Sold Jul 2026

221 Dutchess Rd, Chestertown, MD 21620-2211, United States

Chestertown, MD 21620

3 bd · 2 ba · 2,260 sqft

$365,000Sold Jul 2026

23264 CLARISSA RD,CHESTERTOWN,MD,21620,KENT

Chestertown, MD 21620

3 bd · 2 ba · 1,248 sqft

$541,500Sold Jul 2026

110 S QUEEN STREET

Chestertown, MD 21620

3 bd · 2 ba · 1,785 sqft

$535,000Sold Jul 2026

9816 Fairlee Rd, Chestertown, MD 21620-3821, United States

Chestertown, MD 21620

3 bd · 3 ba · 1,624 sqft

$320,000Sold Jul 2026

10584 KLAMATH ROAD

Chestertown, MD 21620

3 bd · 2 ba · 0 sqft

$165,000Sold Jul 2026

144 Prospect St, Chestertown, MD 21620-1127, United States

Chestertown, MD 21620

2 bd · 2 ba · 1,082 sqft

$205,000Sold Jul 2026

21363 LYNN LANE

Chestertown, MD 21620

3 bd · 1 ba · 1,314 sqft

$85,000Sold Jun 2026

108 PINE STREET

Chestertown, MD 21620

3 bd · 1 ba · 910 sqft

$1,650,000Sold Jun 2026

114 Chester Vw, Chestertown, MD 21620-2139, United States

Chestertown, MD 21620

3 bd · 2 ba · 2,064 sqft

$384,000Sold Jun 2026

23416 CLOQUET ROAD

Chestertown, MD 21620

3 bd · 2 ba · 1,512 sqft

$1,550,000Sold Jun 2026

7761 Broad Neck Rd, Chestertown, MD 21620-4626, United States

Chestertown, MD 21620

5 bd · 3 ba · 2,700 sqft

$460,000Sold Jun 2026

118 GRANT COURT

Chestertown, MD 21620

3 bd · 2 ba · 1,664 sqft

$190,000Sold Jun 2026

423 CALVERT STREET

Chestertown, MD 21620

3 bd · 2 ba · 1,136 sqft

$410,000Sold Jun 2026

109 S COLLEGE AVE,CHESTERTOWN,MD,21620,KENT

Chestertown, MD 21620

3 bd · 3 ba · 1,216 sqft

$525,000Sold Jun 2026

1014 TWIN COURT

Chestertown, MD 21620

3 bd · 2 ba · 1,817 sqft

$1,050,000Sold Jun 2026

231 RICHARD DR,CHESTERTOWN,MD,21620,KENT

Chestertown, MD 21620

5 bd · 3 ba · 2,956 sqft

$395,000Sold Jun 2026

8629 AIRY HILL ROAD

Chestertown, MD 21620

3 bd · 2 ba · 1,440 sqft

$855,000Sold Jun 2026

205 RIVER ROAD

Chestertown, MD 21620

4 bd · 3 ba · 2,877 sqft

$325,000Sold Jun 2026

202 Valley Rd, Chestertown, MD 21620-1415, United States

Chestertown, MD 21620

3 bd · 1 ba · 1,427 sqft

$249,000Sold Jun 2026

112 ELM STREET

Chestertown, MD 21620

3 bd · 1 ba · 1,356 sqft

$360,000Sold Jun 2026

720 DEEP LANDING ROAD

Chestertown, MD 21620

3 bd · 2 ba · 1,271 sqft

$135,000Sold Jun 2026

127 WOOD DUCK LANE

Chestertown, MD 21620

3 bd · 2 ba · 1,666 sqft

$112,500Sold Jun 2026

21324 PERSIMMON DRIVE

Chestertown, MD 21620

2 bd · 1 ba · 1,232 sqft

$293,000Sold Jun 2026

301 Lincoln Dr, Chestertown, MD 21620-3334, United States

Chestertown, MD 21620

3 bd · 2 ba · 1,152 sqft

$349,500Sold Jun 2026

126 CHAR NOR MANOR BOULEVARD

Chestertown, MD 21620

3 bd · 2 ba · 1,304 sqft

$660,000Sold Jun 2026

118 Little Harbor Way, Chestertown, MD 21620-4775, United States

Chestertown, MD 21620

3 bd · 2 ba · 1,600 sqft

$175,000Sold Jun 2026

113 PEAR TREE POINT ROAD

Chestertown, MD 21620

3 bd · 1 ba · 1,296 sqft

$339,900Sold Jun 2026

21125 IOWA AVENUE

Chestertown, MD 21620

2 bd · 1 ba · 1,294 sqft

$290,000Sold Jun 2026

115 ACORN DRIVE

Chestertown, MD 21620

2 bd · 3 ba · 1,864 sqft

$525,000Sold May 2026

22360 Great Oak Landing Rd, Chestertown, MD 21620-4105, United States

Chestertown, MD 21620

5 bd · 4 ba · 2,688 sqft

$430,000Sold May 2026

201 BIRCH RUN ROAD

Chestertown, MD 21620

3 bd · 2 ba · 1,588 sqft

$365,000Sold May 2026

2032 PONDTOWN ROAD

Chestertown, MD 21620

3 bd · 2 ba · 1,120 sqft

$329,000Sold May 2026

10594 MILLBROOK DRIVE

Chestertown, MD 21620

3 bd · 2 ba · 1,499 sqft

$300,000Sold May 2026

154 LONGFELLOW DRIVE

Chestertown, MD 21620

3 bd · 1 ba · 1,408 sqft

$264,900Sold May 2026

109 METCALF RD,CHESTERTOWN,MD,21620,KENT

Chestertown, MD 21620

3 bd · 2 ba · 1,280 sqft

$825,000Sold May 2026

25475 TURNBERRY COURT

Chestertown, MD 21620

4 bd · 4 ba · 4,145 sqft

$545,000Sold Apr 2026

206 S WATER ST,CHESTERTOWN,MD,21620,KENT

Chestertown, MD 21620

4 bd · 3 ba · 2,008 sqft

$552,000Sold Apr 2026

216 Blakefield Dr, Chestertown, MD 21620-2378, United States

Chestertown, MD 21620

4 bd · 3 ba · 2,400 sqft

$295,000Sold Mar 2026

107 Oak Leaf

Chestertown, MD 21620

3 bd · 3 ba · 1,947 sqft

$665,000Sold Mar 2026

118 Little Harbor Unit#201

Chestertown, MD 21620

2 bd · 3 ba · 1,600 sqft

$350,000Sold Mar 2026

10751 Millbrook

Chestertown, MD 21620

3 bd · 2 ba · 1,942 sqft

$459,000Sold Mar 2026

105 Pearl Creek

Chestertown, MD 21620

3 bd · 3 ba · 1,961 sqft

$180,000Sold Mar 2026

9925 Flatland

Chestertown, MD 21620

3 bd · 2 ba · 1,368 sqft

$340,000Sold Mar 2026

204 Rolling

Chestertown, MD 21620

0 bd · 0 ba · 2,296 sqft

$270,000Sold Mar 2026

119 Darden

Chestertown, MD 21620

3 bd · 2 ba · 1,424 sqft

$270,000Sold Mar 2026

119 DARDEN RD,CHESTERTOWN,MD,21620,QUEEN ANNES

Chestertown, MD 21620

3 bd · 2 ba · 1,424 sqft

$325,000Sold Mar 2026

121 Primrose

Chestertown, MD 21620

3 bd · 3 ba · 2,034 sqft

$650,000Sold Mar 2026

200 Washington

Chestertown, MD 21620

2 bd · 4 ba · 2,917 sqft

$175,000Sold Mar 2026

23069 Raleigh

Chestertown, MD 21620

2 bd · 0 ba · 1,160 sqft

$317,000Sold Mar 2026

213 Central

Chestertown, MD 21620

3 bd · 2 ba · 1,232 sqft

$350,000Sold Mar 2026

21111 Texas

Chestertown, MD 21620

3 bd · 2 ba · 1,680 sqft

$125,000Sold Mar 2026

423 Calvert

Chestertown, MD 21620

3 bd · 2 ba · 1,136 sqft

$650,000Sold Feb 2026

109 Water

Chestertown, MD 21620

4 bd · 2 ba · 2,064 sqft

$120,000Sold Feb 2026

141 Prospect

Chestertown, MD 21620

4 bd · 2 ba · 1,156 sqft

$120,000Sold Feb 2026

141 PROSPECT ST,CHESTERTOWN,MD,21620,KENT

Chestertown, MD 21620

4 bd · 2 ba · 1,156 sqft

$364,900Sold Feb 2026

108 Flying Cloud

Chestertown, MD 21620

4 bd · 3 ba · 1,936 sqft

$800,000Sold Feb 2026

4671 Cliffs City

Chestertown, MD 21620

3 bd · 2 ba · 1,783 sqft

$270,000Sold Feb 2026

24339 Chestertown

Chestertown, MD 21620

3 bd · 1 ba · 960 sqft

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Listing information is provided through IDX courtesy Keller Williams Capital Properties.

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