Movoto Real Estate

Homes Under $400K Price For Sale in Chestertown, MD

86 Homes
 
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
104 Lincoln Dr, Chestertown, MD 21620
  • $295,000
  • 3Bd
  • 1Ba
  • 960 Sq Ft
$5K
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
101 S College Ave, Chestertown, MD 21620
  • $359,000
  • 2Bd
  • 2Ba
  • 1,036 Sq Ft
$10K
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
7982 Radcliffe Rd, Chestertown, MD 21620
  • $399,000
  • 2Bd
  • 2Ba
  • 1,904 Sq Ft
$56K
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
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
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
8886 Georgetown Rd, Chestertown, MD 21620
  • $69,900
  • 4.03 Acre
$10.1K
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
Map 36 Parcel 80 Watertower Road, Chestertown, MD 21620
  • $55,000
  • 0.7 Acre
Sandy Bottom Road, Chestertown, MD 21620
  • $49,000
  • 1.95 Acre
$10K
109 2nd St, Chestertown, MD 21620
  • $135,000
  • 1.8 Acre
$15K
8706 Elm Rd, Chestertown, MD 21620
  • $315,000
  • 3Bd
  • 2Ba
  • 1,232 Sq Ft
$5K
Cogar Road, Chestertown, MD 21620
  • $3,000
  • 0.34 Acre
2 Scheeler Road, Chestertown, MD 21620
  • $250,000
  • 0.85 Acre
3 Haacke Drive, Chestertown, MD 21620
  • $225,000
  • 0.87 Acre
Tonopah Road, Chestertown, MD 21620
  • $3,000
  • 0.34 Acre
Lenapah Rd, Chestertown, MD 21620
  • $3,000
  • 0.34 Acre
0 Round Top Rd, Chestertown, MD 21620
  • $200,000
  • 5.81 Acre
117 Water St N #2B, Chestertown, MD 21620
  • $350,000
  • 1Bd
  • 1Ba
  • 850 Sq Ft
117 Water St N #2A, Chestertown, MD 21620
  • $375,000
  • 2Bd
  • 1Ba
  • 787 Sq Ft
117 Water St N #1B, Chestertown, MD 21620
  • $200,000
  • 1Bd
  • 1Ba
  • 700 Sq Ft
22681 Wood Yard Ln, Chestertown, MD 21620
  • $15,000
  • 0.52 Acre
6746 Quaker Neck Rd, Chestertown, MD 21620
  • $339,000
  • 5Bd
  • 3Ba
  • 3,371 Sq Ft
$10K
1 - 50 of 86 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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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.
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