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Homes Recently Sold in Chestertown, MD | Page 9

584 Homes
 
Landing Ln, Chestertown, MD 21620
  • $815,000
  • 3Bd
  • 4Ba
  • 2,200 Sq Ft
SOLD
Lots 233 & 234 Clarissa, Chestertown, MD 21620
  • $3,000
  • 0.46 Acre
SOLD
214 Richard Dr, Chestertown, MD 21620
  • $395,000
  • 2Bd
  • 3Ba
  • 1,723 Sq Ft
SOLD
10605 Tonopah Rd, Chestertown, MD 21620
  • $299,900
  • 4Bd
  • 2Ba
  • 1,248 Sq Ft
SOLD
Caulks Field Road, Chestertown, MD 21620
  • $30,000
  • 0.67 Acre
SOLD
122 1st St, Chestertown, MD 21620
  • $135,000
  • 2Bd
  • 1Ba
  • 720 Sq Ft
SOLD
124 Edmore Rd, Chestertown, MD 21620
  • $252,000
  • 3Bd
  • 1Ba
  • 1,056 Sq Ft
SOLD
118 Westwood Ln, Chestertown, MD 21620
  • $612,500
  • 3Bd
  • 2Ba
  • 2,248 Sq Ft
SOLD
193 Westwood Ln, Chestertown, MD 21620
  • $550,000
  • 3Bd
  • 2Ba
  • 3,572 Sq Ft
SOLD
209 Myers Rd, Chestertown, MD 21620
  • $383,000
  • 3Bd
  • 2Ba
  • 1,846 Sq Ft
SOLD
22900 Handy Point Road Handy Point Rd, Chestertown, MD 21620
  • $1,700,000
  • 5Bd
  • 5Ba
  • 4,885 Sq Ft
SOLD
313 River Rd, Chestertown, MD 21620
  • $380,000
  • 4Bd
  • 3Ba
  • 2,080 Sq Ft
SOLD
510 Truslow Rd, Chestertown, MD 21620
  • $265,000
  • 9.25 Acre
SOLD
0 Gateway Dr, Chestertown, MD 21620
  • $100,000
  • 1.09 Acre
SOLD
105 Sutton Way, Chestertown, MD 21620
  • $405,000
  • 4Bd
  • 3Ba
  • 2,064 Sq Ft
SOLD
21357 Belair, Chestertown, MD 21620
  • $360,000
  • 3Bd
  • 3Ba
  • 2,008 Sq Ft
SOLD
5772 Johnsontown Rd, Chestertown, MD 21620
  • $340,000
  • 3Bd
  • 2Ba
  • 1,344 Sq Ft
SOLD
331 Park Ln, Chestertown, MD 21620
  • $1,120,000
  • 4Bd
  • 2Ba
  • 2,184 Sq Ft
SOLD
Elm Road, Chestertown, MD 21620
  • $34,500
  • 0.37 Acre
SOLD
116 Riverside Ter #7, Chestertown, MD 21620
  • $405,000
  • 2Bd
  • 2Ba
  • 900 Sq Ft
SOLD
529 Cannon St, Chestertown, MD 21620
  • $385,000
  • 3Bd
  • 2Ba
  • 1,288 Sq Ft
SOLD
103 Trafford Dr, Chestertown, MD 21620
  • $299,000
  • 3Bd
  • 3Ba
  • 1,944 Sq Ft
SOLD
125 Evergreen Farm Ln, Chestertown, MD 21620
  • $582,000
  • 1Bd
  • 1Ba
  • 1,296 Sq Ft
SOLD
106 Metcalf Rd, Chestertown, MD 21620
  • $234,900
  • 3Bd
  • 2Ba
SOLD
204 N Mill St, Chestertown, MD 21620
  • $370,000
  • 5Bd
  • 4Ba
  • 2,890 Sq Ft
SOLD
10570 Cogar Rd, Chestertown, MD 21620
  • $349,000
  • 3Bd
  • 2Ba
  • 2,862 Sq Ft
SOLD
27370 Morgnec Rd, Chestertown, MD 21620
  • $300,000
  • 3Bd
  • 2Ba
  • 1,008 Sq Ft
SOLD
Fox Chase Road, Chestertown, MD 21620
  • $375,000
  • 22.64 Acre
SOLD
614 High St, Chestertown, MD 21620
  • $210,000
  • 2Bd
  • 2Ba
  • 1,064 Sq Ft
SOLD
612 High St, Chestertown, MD 21620
  • $195,000
  • 2Bd
  • 2Ba
  • 1,064 Sq Ft
SOLD
207 N Queen St, Chestertown, MD 21620
  • $645,000
  • 4Bd
  • 2Ba
  • 2,244 Sq Ft
SOLD
703 High St, Chestertown, MD 21620
  • $280,000
  • 4Bd
  • 2Ba
  • 1,200 Sq Ft
SOLD
114 Truslow Farm Ln, Chestertown, MD 21620
  • $252,000
  • 5.32 Acre
SOLD
500 Truslow Rd, Chestertown, MD 21620
  • $140,000
  • 1.91 Acre
SOLD
1006 Twin Ct, Chestertown, MD 21620
  • $315,000
  • 3Bd
  • 3Ba
  • 1,800 Sq Ft
SOLD
200 Ashley Ln, Chestertown, MD 21620
  • $420,000
  • 3Bd
  • 2Ba
  • 1,656 Sq Ft
SOLD
202 Byford Dr, Chestertown, MD 21620
  • $402,500
  • 3Bd
  • 2Ba
  • 1,632 Sq Ft
SOLD
104 Silver Heel Dr, Chestertown, MD 21620
  • $360,000
  • 5Bd
  • 4Ba
  • 2,540 Sq Ft
SOLD
148 Grant Ct, Chestertown, MD 21620
  • $440,000
  • 3Bd
  • 2Ba
  • 1,664 Sq Ft
SOLD
7509 Sunburst Ave, Chestertown, MD 21620
  • $230,000
  • 3Bd
  • 1Ba
  • 1,026 Sq Ft
SOLD
23829 E Fork Dr, Chestertown, MD 21620
  • $1,770,000
  • 3Bd
  • 5Ba
  • 3,342 Sq Ft
SOLD
21321 Persimmon Dr, Chestertown, MD 21620
  • $155,000
  • 2Bd
  • 1Ba
  • 1,232 Sq Ft
SOLD
104 W Campus Ave, Chestertown, MD 21620
  • $850,000
  • 3Bd
  • 5Ba
  • 2,884 Sq Ft
SOLD
245 Island Lark Way, Chestertown, MD 21620
  • $272,490
  • 3Bd
  • 3Ba
  • 1,365 Sq Ft
SOLD
Church Hill Road, Chestertown, MD 21620
  • $130,000
  • 5.34 Acre
SOLD
8970 Cumberland St, Chestertown, MD 21620
  • $240,000
  • 2Bd
  • 2Ba
  • 1,069 Sq Ft
SOLD
228 Dutchess Rd, Chestertown, MD 21620
  • $220,000
  • 4Bd
  • 2Ba
  • 1,796 Sq Ft
SOLD
208 N Lynchburg St, Chestertown, MD 21620
  • $199,900
  • 3Bd
  • 1Ba
  • 1,026 Sq Ft
SOLD
114 Metcalf Rd, Chestertown, MD 21620
  • $234,500
  • 3Bd
  • 2Ba
SOLD
9096 Fairlee Rd, Chestertown, MD 21620
  • $355,500
  • 3Bd
  • 2Ba
  • 1,104 Sq Ft
SOLD
401 - 450 of 584 Homes in Chestertown, MD
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Chestertown, MD Real Estate Snapshot

List Price
$440,000
$/Sqft
$259
Homes For Sale
90
Home Size
1,964 Sqft
Days on Movoto
76

Frequently Asked Questions about Chestertown, MD

The Movoto Advantage
Movoto gives you access to the most up-to-the-minute real estate information 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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The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Movoto participates, and is provided by BRIGHT through a licensing agreement.The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated: 7/1/2026. Some properties which appear for sale on this website may no longer be available because they are under contract, have Closedor are no longer being offered for sale. Some real estate firms do not participate in IDX and their listings do not appear on this website. Some properties listed with participating firms do not appear on this website at the request of the seller. This home sale information is not to be construed as an appraisal and may not be used as such for any purpose. BRIGHTMLS is the (or a) provider of this home sale information and has compiled content from various sources. Some properties represented may not have actually solddue to reporting errors.
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