Movoto Real Estate

Chestertown, MD Homes for Sale & Real Estate

128 Homes
 
331 Devon Dr, Chestertown, MD 21620
  • $499,999
  • 4Bd
  • 4Ba
  • 3,506 Sq Ft
10 Cedar Chase Ct, Chestertown, MD 21620
  • $495,000
  • 3Bd
  • 3Ba
  • 1,656 Sq Ft
6324 Quaker Neck Rd, Chestertown, MD 21620
  • $2,895,000
  • 5Bd
  • 4Ba
  • 5,938 Sq Ft
22974 Bay Shore Rd, Chestertown, MD 21620
  • $329,900
  • 2Bd
  • 2Ba
  • 1,440 Sq Ft
8732 Elm Rd, Chestertown, MD 21620
  • $289,000
  • 3Bd
  • 2Ba
  • 1,056 Sq Ft
Open SAT 2-3
24775 Langford Rd, Chestertown, MD 21620
  • $315,000
  • 3Bd
  • 1Ba
  • 1,008 Sq Ft
8276 Broad Neck Rd, Chestertown, MD 21620
  • $1,295,000
  • 4Bd
  • 4Ba
  • 3,383 Sq Ft
104 Lincoln Dr, Chestertown, MD 21620
  • $295,000
  • 3Bd
  • 1Ba
  • 960 Sq Ft
$5K
Undisclosed, Chestertown, MD 21620
  • $695,000
  • 42.59 Acre
Towhee Road, Chestertown, MD 21620
  • $50,000
  • 0.55 Acre
217 Edmore Rd, Chestertown, MD 21620
  • $335,000
  • 3Bd
  • 2Ba
  • 1,398 Sq Ft
$10K
27942 Old Morgnec Rd, Chestertown, MD 21620
  • $89,000
  • 5.17 Acre
7415 Wilkins Ln, Chestertown, MD 21620
  • $229,000
  • 3Bd
  • 1Ba
  • 936 Sq Ft
115 Chester Arms Dr, Chestertown, MD 21620
  • $263,000
  • 3Bd
  • 2Ba
  • 1,140 Sq Ft
300 S And 302 S Mill St, Chestertown, MD 21620
  • $1,195,000
  • 0.46 Acre
212 Washington Ave, Chestertown, MD 21620
  • $675,000
  • 5Bd
  • 3Ba
  • 2,838 Sq Ft
Open SAT 10-1
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
1003 Twin Ct, Chestertown, MD 21620
  • $499,900
  • 3Bd
  • 3Ba
  • 2,076 Sq Ft
$25K
23208 Buck Neck Rd, Chestertown, MD 21620
  • $349,900
  • 3Bd
  • 3Ba
  • 1,650 Sq Ft
123 Trafford Dr, Chestertown, MD 21620
  • $370,000
  • 4Bd
  • 3Ba
  • 2,504 Sq Ft
$5K
124 Wilton Rd, Chestertown, MD 21620
  • $299,900
  • 3Bd
  • 1Ba
  • 1,056 Sq Ft
216 Birch Run Rd, Chestertown, MD 21620
  • $750,000
  • 3Bd
  • 3Ba
  • 2,176 Sq Ft
7982 Radcliffe Rd, Chestertown, MD 21620
  • $399,000
  • 2Bd
  • 2Ba
  • 1,904 Sq Ft
$56K
8630 Elm Rd, Chestertown, MD 21620
  • $424,900
  • 5Bd
  • 3Ba
  • 1,936 Sq Ft
$20.1K
10540 Tonopah Rd, Chestertown, MD 21620
  • $269,000
  • 3Bd
  • 2Ba
  • 1,404 Sq Ft
$10K
Cannon Street, Chestertown, MD 21620
  • $281,000
  • 0.29 Acre
$169K
Cannon Street, Chestertown, MD 21620
  • $196,000
  • 0.22 Acre
$154K
620 Cannon St, Chestertown, MD 21620
  • $85,000
  • 0.07 Acre
$14.9K
129 Trafford Dr, Chestertown, MD 21620
  • $480,000
  • 3Bd
  • 3Ba
  • 3,176 Sq Ft
1010 Twin Ct, Chestertown, MD 21620
  • $365,000
  • 4Bd
  • 2Ba
  • 1,476 Sq Ft
$4.9K
201 N Lynchburg Street Lots 4 5 6 7 St #LOT S 4, 5, 6 & 7, Chestertown, MD 21620
  • $300,000
  • 0.1 Acre
115 Metcalf Rd, Chestertown, MD 21620
  • $259,900
  • 3Bd
  • 2Ba
  • 1,280 Sq Ft
Open THU 6-7
200 Manor Ave, Chestertown, MD 21620
  • $325,000
  • 4Bd
  • 2Ba
  • 2,198 Sq Ft
305 Roosevelt Dr, Chestertown, MD 21620
  • $45,000
  • 0.61 Acre
$15K
121 Metcalf Rd, Chestertown, MD 21620
  • $264,900
  • 3Bd
  • 2Ba
233 Merganser Dr, Chestertown, MD 21620
  • $60,000
  • 0.5 Acre
7680 Country Club Ln, Chestertown, MD 21620
  • $825,000
  • 5Bd
  • 4Ba
  • 2,639 Sq Ft
$60K
9126 Fairlee Rd, Chestertown, MD 21620
  • $314,000
  • 3Bd
  • 2Ba
  • 1,216 Sq Ft
$10K
896 Washington Ave, Chestertown, MD 21620
  • $325,000
  • 3Bd
  • 1Ba
  • 1,000 Sq Ft
104 Conley Dr, Chestertown, MD 21620
  • $239,900
  • 3Bd
  • 2Ba
  • 1,280 Sq Ft
$7.1K
Fairlee Road, Chestertown, MD 21620
  • $75,000
  • 2.2 Acre
234 N College Ave, Chestertown, MD 21620
  • $85,000
  • 2Bd
  • 1Ba
  • 1,296 Sq Ft
$5K
104 Acorn Dr, Chestertown, MD 21620
  • $275,000
  • 3Bd
  • 3Ba
  • 1,900 Sq Ft
$9.9K
8796 Maryland Pkwy, Chestertown, MD 21620
  • $1,495,000
  • 9Bd
  • 7Ba
  • 4,776 Sq Ft
$155K
8886 Georgetown Rd, Chestertown, MD 21620
  • $69,900
  • 4.03 Acre
$10.1K
10781 Fermoy Rd, Chestertown, MD 21620
  • $429,500
  • 4Bd
  • 3Ba
  • 2,160 Sq Ft
$400
1906 Pondtown Rd, Chestertown, MD 21620
  • $110,000
  • 1.93 Acre
23741 L Rd, Chestertown, MD 21620
  • $15,000
  • 1 Acre
956 Washington Ave, Chestertown, MD 21620
  • $275,000
  • 3Bd
  • 1Ba
  • 1,248 Sq Ft
$10K
1 - 50 of 128 Homes for sale in Chestertown, MD
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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?
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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: 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.
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