Movoto Real Estate

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

78 Homes
 
125 Skippers Ln, Chestertown, MD 21620
  • $399,000
  • 3Bd
  • 2Ba
  • 1,080 Sq Ft
New 13 Hours
305 Roosevelt Dr, Chestertown, MD 21620
  • $40,000
  • 0.61 Acre
229 Merganser Dr, Chestertown, MD 21620
  • $50,000
  • 1Bd
  • 1Ba
  • 924 Sq Ft
New 3 Days
201 Garland Way, Chestertown, MD 21620
  • $375,000
  • 4Bd
  • 3Ba
  • 2,886 Sq Ft
New 4 Days
403 Calvert St, Chestertown, MD 21620
  • $135,000
  • 3Bd
  • 2Ba
  • 1,136 Sq Ft
7545 Quaker Neck Rd, Chestertown, MD 21620
  • $175,000
  • 3Bd
  • 1Ba
  • 1,360 Sq Ft
501 High St, Chestertown, MD 21620
  • $349,900
  • —Bd
  • —Ba
  • 2,008 Sq Ft
8668 Elm Rd, Chestertown, MD 21620
  • $349,900
  • 4Bd
  • 2Ba
  • 1,440 Sq Ft
326 Talbot Blvd, Chestertown, MD 21620
  • $399,990
  • 4Bd
  • 3Ba
  • 2,397 Sq Ft
$20K
24607 Chestertown Rd, Chestertown, MD 21620
  • $365,000
  • 3Bd
  • 3Ba
  • 2,294 Sq Ft
21338 Virginia Ave, Chestertown, MD 21620
  • $400,000
  • 2Bd
  • 2Ba
  • 1,000 Sq Ft
330 Talbot Blvd, Chestertown, MD 21620
  • $399,990
  • 3Bd
  • 2Ba
  • 2,603 Sq Ft
8820 Cumberland St, Chestertown, MD 21620
  • $281,500
  • 3Bd
  • 2Ba
  • 1,080 Sq Ft
$31K
103 Metcalf Rd, Chestertown, MD 21620
  • $259,900
  • 3Bd
  • 3Ba
  • 1,280 Sq Ft
Open SAT 11-1
22974 Bay Shore Rd, Chestertown, MD 21620
  • $315,000
  • 2Bd
  • 2Ba
  • 1,440 Sq Ft
$14.9K
24775 Langford Rd, Chestertown, MD 21620
  • $305,000
  • 3Bd
  • 1Ba
  • 1,008 Sq Ft
$10K
8732 Elm Rd, Chestertown, MD 21620
  • $289,000
  • 3Bd
  • 2Ba
  • 1,056 Sq Ft
104 Lincoln Dr, Chestertown, MD 21620
  • $275,000
  • 3Bd
  • 1Ba
  • 960 Sq Ft
$10K
Towhee Road, Chestertown, MD 21620
  • $40,000
  • 0.55 Acre
$10K
115 Chester Arms Dr, Chestertown, MD 21620
  • $259,000
  • 3Bd
  • 2Ba
  • 1,140 Sq Ft
$4K
7415 Wilkins Ln, Chestertown, MD 21620
  • $222,000
  • 3Bd
  • 1Ba
  • 936 Sq Ft
$7K
101 S College Ave, Chestertown, MD 21620
  • $359,000
  • 2Bd
  • 2Ba
  • 1,036 Sq Ft
$10K
123 Trafford Dr, Chestertown, MD 21620
  • $370,000
  • 4Bd
  • 3Ba
  • 2,504 Sq Ft
$5K
10540 Tonopah Rd, Chestertown, MD 21620
  • $267,000
  • 3Bd
  • 2Ba
  • 1,404 Sq Ft
$2K
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
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
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
  • $299,500
  • 3Bd
  • 2Ba
  • 1,216 Sq Ft
$14K
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
  • $79,000
  • 2Bd
  • 1Ba
  • 1,296 Sq Ft
$6K
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
  • $125,000
  • 1.8 Acre
$10K
2 Scheeler Road, Chestertown, MD 21620
  • $250,000
  • 0.85 Acre
3 Haacke Drive, Chestertown, MD 21620
  • $225,000
  • 0.87 Acre
0 Round Top Rd, Chestertown, MD 21620
  • $200,000
  • 5.81 Acre
22681 Wood Yard Ln, Chestertown, MD 21620
  • $15,000
  • 0.52 Acre
Georgetown Road, Chestertown, MD 21620
  • $90,000
  • 3.92 Acre
$500
222 Dutchess Rd, Chestertown, MD 21620
  • $298,000
  • 3Bd
  • 2Ba
  • 1,096 Sq Ft
$22K
1 - 50 of 78 Homes for sale in Chestertown, MD
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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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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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