Movoto Real Estate

Homes Recently Sold in Chestertown, MD

589 Homes
 
8999 Orchard Dr, Chestertown, MD 21620
  • $824,900
  • 5Bd
  • 4Ba
  • 4,353 Sq Ft
SOLD 11/12/26
200 Manor Ave, Chestertown, MD 21620
  • $325,000
  • 4Bd
  • 2Ba
  • 2,198 Sq Ft
SOLD 11/12/26
223 Mount Vernon Ave, Chestertown, MD 21620
  • $175,000
  • 4Bd
  • 1Ba
  • 1,816 Sq Ft
SOLD 11/06/26
10484 Cogar Rd, Chestertown, MD 21620
  • $238,000
  • 3Bd
  • 1Ba
  • 1,008 Sq Ft
SOLD 11/05/26
8620 Park Dr, Chestertown, MD 21620
  • $500,500
  • 4Bd
  • 3Ba
  • 2,524 Sq Ft
SOLD 11/05/26
7982 Radcliffe Rd, Chestertown, MD 21620
  • $390,000
  • 2Bd
  • 2Ba
  • 1,904 Sq Ft
SOLD 11/04/26
201 River Rd, Chestertown, MD 21620
  • $629,000
  • 3Bd
  • 2Ba
  • 2,430 Sq Ft
SOLD 10/30/26
213 Byford Dr, Chestertown, MD 21620
  • $350,000
  • 4Bd
  • 2Ba
  • 1,277 Sq Ft
SOLD 10/30/26
21324 Persimmon Dr, Chestertown, MD 21620
  • $175,000
  • 2Bd
  • 1Ba
  • 1,232 Sq Ft
SOLD 10/28/26
7712 Waterview Ln, Chestertown, MD 21620
  • $665,000
  • 3Bd
  • 4Ba
  • 2,716 Sq Ft
SOLD 10/27/26
204 S Water St, Chestertown, MD 21620
  • $545,000
  • 2Bd
  • 2Ba
  • 1,306 Sq Ft
SOLD 10/26/26
7464 Shortall St, Chestertown, MD 21620
  • $300,000
  • 3Bd
  • 2Ba
  • 1,232 Sq Ft
SOLD 10/22/26
109 Parma Rd, Chestertown, MD 21620
  • $325,000
  • 3Bd
  • 2Ba
  • 1,288 Sq Ft
SOLD 10/21/26
204 Double Creek Rd, Chestertown, MD 21620
  • $525,000
  • 3Bd
  • 3Ba
  • 2,927 Sq Ft
SOLD 10/16/26
Sandpiper Road, Chestertown, MD 21620
  • $3,000
  • 0.52 Acre
SOLD 10/15/26
25750 Collins Ave, Chestertown, MD 21620
  • $450,000
  • 3Bd
  • 2Ba
  • 3,262 Sq Ft
SOLD 09/30/26
522 High St, Chestertown, MD 21620
  • $290,000
  • 2Bd
  • 3Ba
  • 1,518 Sq Ft
SOLD 09/30/26
240 Round Top Rd, Chestertown, MD 21620
  • $295,000
  • 3Bd
  • 2Ba
  • 1,132 Sq Ft
SOLD 09/29/26
218 Camelot Dr, Chestertown, MD 21620
  • $495,000
  • 5Bd
  • 4Ba
  • 3,932 Sq Ft
SOLD 09/28/26
249 Island Lark Way, Chestertown, MD 21620
  • $260,000
  • 3Bd
  • 3Ba
  • 1,420 Sq Ft
SOLD 09/22/26
123 Heath Rd, Chestertown, MD 21620
  • $349,000
  • 3Bd
  • 2Ba
  • 1,792 Sq Ft
SOLD 09/22/26
104 Church Aly, Chestertown, MD 21620
  • $445,000
  • 2Bd
  • 2Ba
  • 1,058 Sq Ft
SOLD 09/18/26
240 Merganser Dr, Chestertown, MD 21620
  • $360,000
  • 3Bd
  • 2Ba
  • 1,120 Sq Ft
SOLD 09/16/26
8312 Broad Neck Rd, Chestertown, MD 21620
  • $330,000
  • 3Bd
  • 2Ba
  • 3,292 Sq Ft
SOLD 09/14/26
21146 Montana Ave, Chestertown, MD 21620
  • $290,000
  • 2Bd
  • 2Ba
  • 1,500 Sq Ft
SOLD 09/11/26
202 Pine St, Chestertown, MD 21620
  • $222,000
  • 3Bd
  • 1Ba
  • 1,341 Sq Ft
SOLD 09/08/26
407 High St, Chestertown, MD 21620
  • $725,000
  • 3Bd
  • 5Ba
  • 3,047 Sq Ft
SOLD 09/08/26
207 Lincoln Dr, Chestertown, MD 21620
  • $141,000
  • 4Bd
  • 2Ba
  • 1,152 Sq Ft
SOLD 09/03/26
105 N Water St #2, Chestertown, MD 21620
  • $460,000
  • 2Bd
  • 2Ba
  • 1,011 Sq Ft
SOLD 09/03/26
210 N Queen St, Chestertown, MD 21620
  • $730,000
  • 4Bd
  • 3Ba
  • 2,730 Sq Ft
SOLD 09/01/26
10720 Foreston Rd, Chestertown, MD 21620
  • $316,000
  • 3Bd
  • 2Ba
  • 1,412 Sq Ft
SOLD 09/01/26
101 S Mill St, Chestertown, MD 21620
  • $500,000
  • 2Bd
  • 3Ba
  • 1,476 Sq Ft
SOLD 09/01/26
222 Mount Vernon Ave, Chestertown, MD 21620
  • $433,000
  • 4Bd
  • 2Ba
  • 1,656 Sq Ft
SOLD 09/01/26
103 Maple Ave, Chestertown, MD 21620
  • $615,000
  • 4Bd
  • 3Ba
  • 4,536 Sq Ft
SOLD 08/27/26
107 Conley Dr, Chestertown, MD 21620
  • $245,000
  • 3Bd
  • 1Ba
  • 1,140 Sq Ft
SOLD 08/25/26
517 Round Top Rd, Chestertown, MD 21620
  • $289,000
  • 3Bd
  • 1Ba
  • 1,248 Sq Ft
SOLD 08/21/26
110 Prospect St, Chestertown, MD 21620
  • $55,000
  • 3Bd
  • 2Ba
  • 2,210 Sq Ft
SOLD 08/21/26
7903 Radcliffe Rd, Chestertown, MD 21620
  • $705,000
  • 3Bd
  • 4Ba
  • 4,037 Sq Ft
SOLD 08/19/26
22481 Goose Hollow Dr, Chestertown, MD 21620
  • $335,320
  • 3Bd
  • 2Ba
  • 1,296 Sq Ft
SOLD 08/18/26
107 Flying Cloud Dr, Chestertown, MD 21620
  • $380,000
  • 5Bd
  • 4Ba
  • 2,534 Sq Ft
SOLD 08/18/26
Preston Lane, Chestertown, MD 21620
  • $525,000
  • 3Bd
  • 3Ba
  • 2,824 Sq Ft
SOLD 08/16/26
109 Cedar St, Chestertown, MD 21620
  • $318,000
  • 3Bd
  • 3Ba
  • 1,397 Sq Ft
SOLD 08/14/26
202 Royston Shores Rd, Chestertown, MD 21620
  • $1,200,000
  • 4Bd
  • 3Ba
  • 2,292 Sq Ft
SOLD 08/14/26
25440 Learman Rd, Chestertown, MD 21620
  • $3,000,000
  • 3Bd
  • 4Ba
  • 3,142 Sq Ft
SOLD 08/14/26
102 Flying Cloud Dr, Chestertown, MD 21620
  • $324,000
  • 3Bd
  • 3Ba
  • 1,896 Sq Ft
SOLD 08/14/26
228 Merganser Dr, Chestertown, MD 21620
  • $42,000
  • 0.51 Acre
SOLD 08/14/26
311 Devon Dr, Chestertown, MD 21620
  • $465,000
  • 4Bd
  • 3Ba
  • 3,504 Sq Ft
SOLD 08/14/26
7989 Quaker Neck Rd, Chestertown, MD 21620
  • $1,900,000
  • 5Bd
  • 5Ba
  • 4,305 Sq Ft
SOLD 08/14/26
116 Cross St, Chestertown, MD 21620
  • $104,000
  • 0.18 Acre
SOLD 08/13/26
East Street, Chestertown, MD 21620
  • $75,000
  • 0.48 Acre
SOLD 08/13/26
1 - 50 of 589 Homes in Chestertown, MD
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Chestertown, MD real estate market trends

Statistics as of November 2026
$422K
Avg. list price
$237/Sqft
Avg. price/sqft
90
Homes for sale
1,994 Sqft
Avg. home size
110 Days
Avg. days on market
Movoto makes it easy to track market trends in Chestertown, MD. Whether you’re entering the market or planning your next move, understanding these key metrics can guide smart decisions. Looking for more detailed housing market stats in Chestertown, MD?
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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: 11/12/2026. 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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