Movoto Real Estate

Single Family Homes For Sale in Chestertown, MD

64 Homes
 
8901 S Bayview Dr, Chestertown, MD 21620
  • $525,000
  • 3Bd
  • 3Ba
  • 1,833 Sq Ft
New 39 Hours
21338 Virginia Ave, Chestertown, MD 21620
  • $400,000
  • 2Bd
  • 2Ba
  • 1,000 Sq Ft
New 2 Days
326 Talbolt Blvd, Chestertown, MD 21620
  • $549,990
  • 3Bd
  • 3Ba
  • 3,301 Sq Ft
New 2 Days
330 Talbot Blvd, Chestertown, MD 21620
  • $489,990
  • 3Bd
  • 4Ba
  • 2,603 Sq Ft
New 2 Days
10484 Cogar Rd, Chestertown, MD 21620
  • $238,000
  • 3Bd
  • 1Ba
  • 1,008 Sq Ft
New 2 Days
10 Cedar Chase Ct, Chestertown, MD 21620
  • $495,000
  • 3Bd
  • 3Ba
  • 1,656 Sq Ft
New 4 Days
203 Manor Ave, Chestertown, MD 21620
  • $296,000
  • 3Bd
  • 2Ba
  • 1,248 Sq Ft
New 5 Days
106 Harlan Loop, Chestertown, MD 21620
  • $425,000
  • 4Bd
  • 3Ba
  • 3,165 Sq Ft
New 5 Days
326 Talbot Blvd, Chestertown, MD 21620
  • $529,990
  • 2Bd
  • 2Ba
  • 3,104 Sq Ft
326 Talbot Blvd, Chestertown, MD 21620
  • $474,990
  • 2Bd
  • 2Ba
  • 2,642 Sq Ft
326 Talbot Blvd, Chestertown, MD 21620
  • $509,990
  • 3Bd
  • 3Ba
  • 3,301 Sq Ft
326 Talbot Blvd, Chestertown, MD 21620
  • $499,990
  • 3Bd
  • 2Ba
  • 3,176 Sq Ft
326 Talbot Blvd, Chestertown, MD 21620
  • $439,990
  • 2Bd
  • 2Ba
  • 2,346 Sq Ft
326 Talbot Blvd, Chestertown, MD 21620
  • $564,990
  • 3Bd
  • 3Ba
  • 3,790 Sq Ft
204 S Water St, Chestertown, MD 21620
  • $565,000
  • 2Bd
  • 2Ba
  • 1,306 Sq Ft
8986 Orchard Dr, Chestertown, MD 21620
  • $679,900
  • 3Bd
  • 4Ba
  • 3,228 Sq Ft
234 N Kent St, Chestertown, MD 21620
  • $325,000
  • 5Bd
  • 2Ba
  • 1,802 Sq Ft
212 Washington Ave, Chestertown, MD 21620
  • $675,000
  • 5Bd
  • 3Ba
  • 2,838 Sq Ft
8820 Cumberland St, Chestertown, MD 21620
  • $312,500
  • 3Bd
  • 2Ba
  • 1,080 Sq Ft
329 Union Church Rd, Chestertown, MD 21620
  • $568,900
  • 4Bd
  • 3Ba
  • 2,464 Sq Ft
Open WED 5-7
6324 Quaker Neck Rd, Chestertown, MD 21620
  • $2,895,000
  • 5Bd
  • 4Ba
  • 5,938 Sq Ft
22974 Bay Shore Rd, Chestertown, MD 21620
  • $315,000
  • 2Bd
  • 2Ba
  • 1,440 Sq Ft
$14.9K
8732 Elm Rd, Chestertown, MD 21620
  • $289,000
  • 3Bd
  • 2Ba
  • 1,056 Sq Ft
24775 Langford Rd, Chestertown, MD 21620
  • $305,000
  • 3Bd
  • 1Ba
  • 1,008 Sq Ft
$10K
104 Lincoln Dr, Chestertown, MD 21620
  • $275,000
  • 3Bd
  • 1Ba
  • 960 Sq Ft
$10K
217 Edmore Rd, Chestertown, MD 21620
  • $325,000
  • 3Bd
  • 2Ba
  • 1,398 Sq Ft
$10K
7415 Wilkins Ln, Chestertown, MD 21620
  • $222,000
  • 3Bd
  • 1Ba
  • 936 Sq Ft
$7K
115 Chester Arms Dr, Chestertown, MD 21620
  • $259,000
  • 3Bd
  • 2Ba
  • 1,140 Sq Ft
$4K
8184 Rock Hall Rd, Chestertown, MD 21620
  • $38,200,000
  • 4Bd
  • 2Ba
  • 2,330 Sq Ft
101 S College Ave, Chestertown, MD 21620
  • $359,000
  • 2Bd
  • 2Ba
  • 1,036 Sq Ft
$10K
23208 Buck Neck Rd, Chestertown, MD 21620
  • $319,900
  • 3Bd
  • 3Ba
  • 1,650 Sq Ft
$30K
123 Trafford Dr, Chestertown, MD 21620
  • $370,000
  • 4Bd
  • 3Ba
  • 2,504 Sq Ft
$5K
124 Wilton Rd, Chestertown, MD 21620
  • $294,900
  • 3Bd
  • 1Ba
  • 1,056 Sq Ft
$5K
216 Birch Run Rd, Chestertown, MD 21620
  • $750,000
  • 3Bd
  • 3Ba
  • 2,176 Sq Ft
8630 Elm Rd, Chestertown, MD 21620
  • $399,900
  • 5Bd
  • 3Ba
  • 1,936 Sq Ft
Open SUN 1-3
129 Trafford Dr, Chestertown, MD 21620
  • $480,000
  • 3Bd
  • 3Ba
  • 3,176 Sq Ft
1010 Twin Ct, Chestertown, MD 21620
  • $349,900
  • 4Bd
  • 2Ba
  • 1,476 Sq Ft
$15.1K
7680 Country Club Ln, Chestertown, MD 21620
  • $825,000
  • 5Bd
  • 4Ba
  • 2,639 Sq Ft
$60K
9126 Fairlee Rd, Chestertown, MD 21620
  • $313,500
  • 3Bd
  • 2Ba
  • 1,216 Sq Ft
Open SUN 11-12
896 Washington Ave, Chestertown, MD 21620
  • $325,000
  • 3Bd
  • 1Ba
  • 1,000 Sq Ft
234 N College Ave, Chestertown, MD 21620
  • $85,000
  • 2Bd
  • 1Ba
  • 1,296 Sq Ft
$5K
8796 Maryland Pkwy, Chestertown, MD 21620
  • $1,495,000
  • 9Bd
  • 7Ba
  • 4,776 Sq Ft
$155K
10781 Fermoy Rd, Chestertown, MD 21620
  • $429,500
  • 4Bd
  • 3Ba
  • 2,160 Sq Ft
$400
22470 Fairgale Farm Ln, Chestertown, MD 21620
  • $1,375,000
  • 4Bd
  • 5Ba
  • 4,257 Sq Ft
$75K
103 Sutton Way, Chestertown, MD 21620
  • $509,000
  • 5Bd
  • 4Ba
  • 3,816 Sq Ft
$41K
106 Queen St S, Chestertown, MD 21620
  • $829,000
  • 3Bd
  • 4Ba
  • 2,472 Sq Ft
$36K
6746 Quaker Neck Rd, Chestertown, MD 21620
  • $339,000
  • 5Bd
  • 3Ba
  • 3,371 Sq Ft
$10K
105 High St, Chestertown, MD 21620
  • $1,245,500
  • 5Bd
  • 5Ba
  • 3,243 Sq Ft
$50K
222 Dutchess Rd, Chestertown, MD 21620
  • $320,000
  • 3Bd
  • 2Ba
  • 1,096 Sq Ft
23043 Bay Shore Spur, Chestertown, MD 21620
  • $385,000
  • 4Bd
  • 3Ba
  • 2,630 Sq Ft
$60K
1 - 50 of 64 Houses for sale in Chestertown, MD
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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 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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