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Homes Under $400K Price For Sale in Chestertown, MD | Page 2

86 Homes
 
223 Mount Vernon Ave, Chestertown, MD 21620
  • $200,000
  • 4Bd
  • 1Ba
  • 1,816 Sq Ft
7482 Poplar Ave, Chestertown, MD 21620
  • $275,000
  • 3Bd
  • 1Ba
  • 975 Sq Ft
109 Parma Rd, Chestertown, MD 21620
  • $315,000
  • 3Bd
  • 2Ba
  • 1,288 Sq Ft
533 Round Top Rd, Chestertown, MD 21620
  • $225,000
  • 4Bd
  • 2Ba
  • 1,800 Sq Ft
7464 Shortall St, Chestertown, MD 21620
  • $304,000
  • 3Bd
  • 2Ba
  • 1,232 Sq Ft
Sandpiper Road, Chestertown, MD 21620
  • $4,500
  • 0.52 Acre
21324 Persimmon Dr, Chestertown, MD 21620
  • $179,900
  • 2Bd
  • 1Ba
  • 1,232 Sq Ft
213 Byford Dr, Chestertown, MD 21620
  • $372,000
  • 4Bd
  • 2Ba
  • 1,277 Sq Ft
522 High St, Chestertown, MD 21620
  • $289,900
  • 2Bd
  • 3Ba
  • 1,518 Sq Ft
214 Silver Heel Rd, Chestertown, MD 21620
  • $340,000
  • 4Bd
  • 3Ba
  • 1,972 Sq Ft
Georgetown Road, Chestertown, MD 21620
  • $90,000
  • 3.92 Acre
$500
611 Cannon St, Chestertown, MD 21620
  • $275,000
  • 2Bd
  • 2Ba
  • 920 Sq Ft
222 Dutchess Rd, Chestertown, MD 21620
  • $320,000
  • 3Bd
  • 2Ba
  • 1,096 Sq Ft
Clarissa Road, Chestertown, MD 21620
  • $8,000
  • 0.34 Acre
$2K
404 Spring Rd, Chestertown, MD 21620
  • $19,500
  • 0.99 Acre
23043 Bay Shore Spur, Chestertown, MD 21620
  • $385,000
  • 4Bd
  • 3Ba
  • 2,630 Sq Ft
$60K
Tonopah Rd., Chestertown, MD 21620
  • $40,000
  • 0.34 Acre
Johnsontown Road, Chestertown, MD 21620
  • $10,000
  • 0.9 Acre
$15K
Buck Neck Road, Chestertown, MD 21620
  • $5,000
  • 0.34 Acre
$4K
Kinglet Road, Chestertown, MD 21620
  • $5,000
  • 0.34 Acre
$4K
Georgetown Rd, Chestertown, MD 21620
  • $55,000
  • 3 Acre
$5K
Caulks Field Road, Chestertown, MD 21620
  • $150,000
  • 2 Acre
Georgetown Road Se, Chestertown, MD 21620
  • $150,000
  • 2 Acre
Old Morgnec Road, Chestertown, MD 21620
  • $59,000
  • 1.37 Acre
$5K
Towhee Road, Chestertown, MD 21620
  • $5,000
  • 0.34 Acre
$5K
Bunting Road, Chestertown, MD 21620
  • $5,000
  • 0.34 Acre
$5K
Beltram Rd, Chestertown, MD 21620
  • $5,000
  • 0.34 Acre
$5K
Fish Hatchery Road, Chestertown, MD 21620
  • $5,000
  • 0.37 Acre
$5K
Buck Neck Landing Road, Chestertown, MD 21620
  • $9,500
  • 0.34 Acre
Parcel Buck Neck Ldg Road, Chestertown, MD 21620
  • $5,000
  • 0.34 Acre
$3K
Montgomery Avenue, Chestertown, MD 21620
  • $40,000
  • 0.11 Acre
Redfield Road, Chestertown, MD 21620
  • $38,000
  • 0.34 Acre
$23K
23710 L Rd, Chestertown, MD 21620
  • $24,000
  • 0.5 Acre
$4K
Fish Hatchery Road, Chestertown, MD 21620
  • $37,000
  • 0.34 Acre
$22K
Spinnaker Road, Chestertown, MD 21620
  • $38,000
  • 0.56 Acre
$17K
Sheldrake Drive, Chestertown, MD 21620
  • $10,000
  • 0.34 Acre
$5K
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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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Frequently Asked Questions about 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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