Movoto Real Estate

Homes Recently Sold in Chestertown, MD

584 Homes
 
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
1904 Pondtown Rd, Chestertown, MD 21620
  • $247,500
  • 3Bd
  • 1Ba
  • 1,967 Sq Ft
SOLD 08/10/26
lot9 Prestwick Dr, Chestertown, MD 21620
  • $185,000
  • 1.95 Acre
SOLD 08/10/26
139 Prospect St, Chestertown, MD 21620
  • $195,000
  • 3Bd
  • 1Ba
  • 1,200 Sq Ft
SOLD 07/31/26
304 Hadaway Dr, Chestertown, MD 21620
  • $300,000
  • 4Bd
  • 2Ba
  • 1,325 Sq Ft
SOLD 07/30/26
7844 Chester Ct, Chestertown, MD 21620
  • $640,000
  • 4Bd
  • 3Ba
  • 3,248 Sq Ft
SOLD 07/29/26
21217 Texas Ave, Chestertown, MD 21620
  • $244,000
  • 2Bd
  • 1Ba
  • 912 Sq Ft
SOLD 07/27/26
521 N Kent St, Chestertown, MD 21620
  • $365,000
  • 3Bd
  • 2Ba
  • 1,934 Sq Ft
SOLD 07/22/26
100 Prospect St, Chestertown, MD 21620
  • $215,000
  • 3Bd
  • 1Ba
  • 1,373 Sq Ft
SOLD 07/21/26
10572 Watonga Rd, Chestertown, MD 21620
  • $325,000
  • 3Bd
  • 2Ba
  • 1,404 Sq Ft
SOLD 07/16/26
215 Fairview Dr, Chestertown, MD 21620
  • $435,000
  • 3Bd
  • 3Ba
  • 1,784 Sq Ft
SOLD 07/16/26
704 Truslow Rd, Chestertown, MD 21620
  • $453,000
  • 3Bd
  • 3Ba
  • 2,060 Sq Ft
SOLD 07/14/26
221 Dutchess Rd, Chestertown, MD 21620
  • $228,000
  • 3Bd
  • 2Ba
  • 2,260 Sq Ft
SOLD 07/13/26
23264 Clarissa Rd, Chestertown, MD 21620
  • $365,000
  • 3Bd
  • 2Ba
  • 1,248 Sq Ft
SOLD 07/13/26
110 S Queen St, Chestertown, MD 21620
  • $541,500
  • 3Bd
  • 2Ba
  • 1,785 Sq Ft
SOLD 07/10/26
9816 Fairlee Rd, Chestertown, MD 21620
  • $535,000
  • 3Bd
  • 3Ba
  • 1,624 Sq Ft
SOLD 07/10/26
10584 Klamath Rd, Chestertown, MD 21620
  • $320,000
  • 3Bd
  • 2Ba
SOLD 07/08/26
206 Burchard Sawmill Rd, Chestertown, MD 21620
  • $9,000
  • 1.05 Acre
SOLD 07/08/26
1 - 50 of 584 Homes in Chestertown, MD
1 2 3 4 5 ... 12
By entering my info and clicking Submit below, I am providing my e-signature and express written consent to receive marketing emails, calls, and texts (including via automatic telephone dialing systems, AI generative, artificial or pre-recorded voice technology) relating to my inquiry from Movoto (and parties calling/messaging on their behalf) even if my number appears on the company, state, or national Do Not Call Registry. You also agree to ourTerms and Conditions and Privacy Policy. Consent not required to receive services (call 1-844-420-1270 to be connected without providing consent).

Explore nearby locations

The prices shown are the median list prices.

Narrow your search

Chestertown, MD real estate market trends

Statistics as of September 2026
$380K
Avg. list price
$246/Sqft
Avg. price/sqft
89
Homes for sale
1,936 Sqft
Avg. home size
88 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?
Schools
Ratings provided by great school

Frequently Asked Questions about Real Estate in Chestertown, MD

Meet with a real estate agent today (844) 417-0593
  • Movoto Logo
  • Download IOS APP Download Android APP
The multiple listing information is provided by BRIGHT MLS. IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Buyer to verify all information. The information provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing information updated every 15 minutes. Terms of use & Privacy Policy, California Privacy Info. Copyright © 2005 - 2026 Movoto, Inc. All rights reserved. Equal Housing Opportunity CalDRE CalDRE #01517281
Movoto Real Estate is committed to ensuring accessibility for individuals with disabilities. We are continuously working to improve the accessibility of our web experience for everyone. We welcome feedback and accommodation requests, please submit them here.
© 2026 BRIGHT, All Rights Reserved
Information Deemed Reliable But Not Guaranteed
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: 9/29/2026. 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.
Requests for information regarding mortgage products will be directed to Movoto.com affiliate, Lower, LLC - a licensed Mortgage Lender (NMLS #1124061), or, based on your location, may be redirected to a participating mortgage marketing partner that may pay Lower, LLC for any consumer contact information provided through this site.