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Chestertown Real Estate & Chestertown, MD Homes For Sale | Page 3

118 Homes
 
317 Rolling Rd, Chestertown, MD 21620
  • $229,900
  • 3Bd
  • 2Ba
  • 2,344 Sq Ft
203 Manor Ave, Chestertown, MD 21620
  • $296,000
  • 3Bd
  • 2Ba
  • 1,248 Sq Ft
234 N Kent St, Chestertown, MD 21620
  • $300,000
  • 5Bd
  • 2Ba
  • 1,802 Sq Ft
7482 Poplar Ave, Chestertown, MD 21620
  • $275,000
  • 3Bd
  • 1Ba
  • 975 Sq Ft
23208 Buck Neck Rd, Chestertown, MD 21620
  • $319,900
  • 3Bd
  • 3Ba
  • 1,650 Sq Ft
124 Wilton Rd, Chestertown, MD 21620
  • $294,900
  • 3Bd
  • 1Ba
  • 1,056 Sq Ft
7828 Country Club Ln, Chestertown, MD 21620
  • $799,000
  • 3Bd
  • 3Ba
  • 2,857 Sq Ft
214 Silver Heel Rd, Chestertown, MD 21620
  • $340,000
  • 4Bd
  • 3Ba
  • 1,972 Sq Ft
6746 Quaker Neck Rd, Chestertown, MD 21620
  • $339,000
  • 5Bd
  • 3Ba
  • 3,371 Sq Ft
611 Cannon St, Chestertown, MD 21620
  • $275,000
  • 2Bd
  • 2Ba
  • 920 Sq Ft
Tonopah Rd., Chestertown, MD 21620
  • $40,000
  • 0.34 Acre
Johnsontown Road, Chestertown, MD 21620
  • $10,000
  • 0.9 Acre
Parcel Buck Neck Ldg Road, Chestertown, MD 21620
  • $5,000
  • 0.34 Acre
$3K
Redfield Road, Chestertown, MD 21620
  • $19,000
  • 0.34 Acre
$19K
23710 L Rd, Chestertown, MD 21620
  • $12,000
  • 0.5 Acre
$12K
Fish Hatchery Road, Chestertown, MD 21620
  • $18,500
  • 0.34 Acre
$18.5K
Spinnaker Road, Chestertown, MD 21620
  • $19,000
  • 0.56 Acre
$19K
Sheldrake Drive, Chestertown, MD 21620
  • $10,000
  • 0.34 Acre
$5K
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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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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: 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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