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Single Family Homes For Sale in Chestertown, MD | Page 2

64 Homes
 
7712 Waterview Ln, Chestertown, MD 21620
  • $659,999
  • 3Bd
  • 4Ba
  • 2,716 Sq Ft
223 Mount Vernon Ave, Chestertown, MD 21620
  • $200,000
  • 4Bd
  • 1Ba
  • 1,816 Sq Ft
7482 Poplar Ave, Chestertown, MD 21620
  • $275,000
  • 3Bd
  • 1Ba
  • 975 Sq Ft
109 Parma Rd, Chestertown, MD 21620
  • $315,000
  • 3Bd
  • 2Ba
  • 1,288 Sq Ft
7464 Shortall St, Chestertown, MD 21620
  • $304,000
  • 3Bd
  • 2Ba
  • 1,232 Sq Ft
7982 Radcliffe Rd, Chestertown, MD 21620
  • $399,000
  • 2Bd
  • 2Ba
  • 1,904 Sq Ft
7828 Country Club Ln, Chestertown, MD 21620
  • $799,000
  • 3Bd
  • 3Ba
  • 2,857 Sq Ft
8999 Orchard Dr, Chestertown, MD 21620
  • $824,900
  • 5Bd
  • 4Ba
  • 4,353 Sq Ft
200 Manor Ave, Chestertown, MD 21620
  • $325,000
  • 4Bd
  • 2Ba
  • 2,198 Sq Ft
201 River Rd, Chestertown, MD 21620
  • $629,900
  • 3Bd
  • 2Ba
  • 2,430 Sq Ft
213 Byford Dr, Chestertown, MD 21620
  • $372,000
  • 4Bd
  • 2Ba
  • 1,277 Sq Ft
214 Silver Heel Rd, Chestertown, MD 21620
  • $340,000
  • 4Bd
  • 3Ba
  • 1,972 Sq Ft
611 Cannon St, Chestertown, MD 21620
  • $275,000
  • 2Bd
  • 2Ba
  • 920 Sq Ft
8620 Park Dr, Chestertown, MD 21620
  • $489,900
  • 4Bd
  • 3Ba
  • 2,524 Sq Ft
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Chestertown, MD real estate market trends

Statistics as of October 2026
$392K
Avg. list price
$247/Sqft
Avg. price/sqft
84
Homes for sale
1,964 Sqft
Avg. home size
116 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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Frequently Asked Questions about Chestertown, MD

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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
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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: 10/15/2026. 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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