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Homes Recently Sold in Chestertown, MD | Page 4

589 Homes
 
8833 Georgetown Rd, Chestertown, MD 21620
  • $359,000
  • 4Bd
  • 2Ba
  • 1,625 Sq Ft
SOLD
10121 Fairlee Rd, Chestertown, MD 21620
  • $2,100,000
  • 6Bd
  • 5Ba
  • 4,954 Sq Ft
SOLD
104 Iris Rd, Chestertown, MD 21620
  • $379,000
  • 3Bd
  • 2Ba
  • 1,700 Sq Ft
SOLD
303 Cedar St, Chestertown, MD 21620
  • $325,000
  • 3Bd
  • 3Ba
  • 2,577 Sq Ft
SOLD
165 Char Nor Manor Blvd, Chestertown, MD 21620
  • $424,000
  • 4Bd
  • 3Ba
  • 2,258 Sq Ft
SOLD
108 Primrose Rd, Chestertown, MD 21620
  • $392,500
  • 3Bd
  • 2Ba
  • 1,722 Sq Ft
SOLD
676 Deep Landing Rd, Chestertown, MD 21620
  • $325,000
  • 3Bd
  • 3Ba
  • 1,468 Sq Ft
SOLD
112 Silver Heel Dr, Chestertown, MD 21620
  • $379,900
  • 5Bd
  • 4Ba
  • 2,615 Sq Ft
SOLD
7521 Pine Ave, Chestertown, MD 21620
  • $235,000
  • 3Bd
  • 1Ba
  • 1,040 Sq Ft
SOLD
303 E Campus Ave, Chestertown, MD 21620
  • $364,000
  • 3Bd
  • 2Ba
  • 1,532 Sq Ft
SOLD
318 Lincoln, Chestertown, MD 21620
  • $255,000
  • 3Bd
  • 2Ba
  • 960 Sq Ft
SOLD
107 Malone Ave, Chestertown, MD 21620
  • $290,000
  • 3Bd
  • 1Ba
  • 1,200 Sq Ft
SOLD
100 Metcalf Rd, Chestertown, MD 21620
  • $240,000
  • 3Bd
  • 2Ba
  • 1,140 Sq Ft
SOLD
300 Hickory Ln, Chestertown, MD 21620
  • $1,100,000
  • 5Bd
  • 4Ba
  • 3,640 Sq Ft
SOLD
10230 John Carvill Rd, Chestertown, MD 21620
  • $740,000
  • 4Bd
  • 3Ba
  • 2,350 Sq Ft
SOLD
206 Cannon St, Chestertown, MD 21620
  • $800,000
  • 1.56 Acre
SOLD
206 Valley, Chestertown, MD 21620
  • $590,000
  • 4Bd
  • 2Ba
  • 2,869 Sq Ft
SOLD
26933 Mallard Rd, Chestertown, MD 21620
  • $555,000
  • 3Bd
  • 3Ba
  • 1,600 Sq Ft
SOLD
7653 Broad Neck Rd, Chestertown, MD 21620
  • $375,000
  • 4Bd
  • 3Ba
  • 1,790 Sq Ft
SOLD
lot24 25 Buck Neck Rd, Chestertown, MD 21620
  • $5,000
  • 0.42 Acre
SOLD
411 Greenwood Ave, Chestertown, MD 21620
  • $415,000
  • 3Bd
  • 3Ba
  • 1,676 Sq Ft
SOLD
5700 Johnsontown Rd, Chestertown, MD 21620
  • $80,000
  • 3Bd
  • 1Ba
  • 1,144 Sq Ft
SOLD
492 Pear Tree Point Rd, Chestertown, MD 21620
  • $850,000
  • 3Bd
  • 2Ba
  • 3,720 Sq Ft
SOLD
517 High St, Chestertown, MD 21620
  • $361,500
  • —Bd
  • —Ba
  • 1,728 Sq Ft
SOLD
25195 Lovers Ln, Chestertown, MD 21620
  • $350,000
  • 1Bd
  • 1Ba
  • 1,002 Sq Ft
SOLD
101 Birch Run Rd, Chestertown, MD 21620
  • $475,000
  • 3Bd
  • 2Ba
  • 1,961 Sq Ft
SOLD
23393 Cacaway Farm Ln, Chestertown, MD 21620
  • $1,150,000
  • 3Bd
  • 4Ba
  • 4,446 Sq Ft
SOLD
101 Metcalf Rd, Chestertown, MD 21620
  • $264,900
  • 3Bd
  • 2Ba
  • 1,280 Sq Ft
SOLD
302 Rosin Dr, Chestertown, MD 21620
  • $550,000
  • 5Bd
  • 4Ba
  • 3,877 Sq Ft
SOLD
600 Rosin Dr, Chestertown, MD 21620
  • $413,300
  • 3Bd
  • 2Ba
  • 1,300 Sq Ft
SOLD
7483 Shortall St, Chestertown, MD 21620
  • $287,500
  • 3Bd
  • 2Ba
  • 1,232 Sq Ft
SOLD
8951 Orchard Dr, Chestertown, MD 21620
  • $700,000
  • 4Bd
  • 4Ba
  • 3,735 Sq Ft
SOLD
119 High St, Chestertown, MD 21620
  • $1,165,000
  • 5Bd
  • 5Ba
  • 4,409 Sq Ft
SOLD
907 N Meadowview Dr, Chestertown, MD 21620
  • $375,000
  • 3Bd
  • 3Ba
  • 1,842 Sq Ft
SOLD
212 Landing Ln, Chestertown, MD 21620
  • $750,000
  • 3Bd
  • 4Ba
SOLD
221 Old Bridge Rd, Chestertown, MD 21620
  • $359,900
  • 3Bd
  • 2Ba
  • 1,851 Sq Ft
SOLD
23620 Lands End Rd, Chestertown, MD 21620
  • $4,221,800
  • 5Bd
  • 8Ba
  • 9,852 Sq Ft
SOLD
10761 Kasota Rd, Chestertown, MD 21620
  • $872,500
  • 3Bd
  • 3Ba
  • 2,582 Sq Ft
SOLD
126 Metcalf Rd, Chestertown, MD 21620
  • $230,000
  • 3Bd
  • 2Ba
  • 1,140 Sq Ft
SOLD
201 Boundary Ave, Chestertown, MD 21620
  • $425,000
  • 3Bd
  • 3Ba
  • 3,096 Sq Ft
SOLD
10050 Forrest Ln, Chestertown, MD 21620
  • $905,000
  • 4Bd
  • 2Ba
  • 1,820 Sq Ft
SOLD
23628 Canvasback Rd, Chestertown, MD 21620
  • $25,000
  • 0.34 Acre
SOLD
105 Parma Rd, Chestertown, MD 21620
  • $322,000
  • 3Bd
  • 2Ba
  • 1,232 Sq Ft
SOLD
103 Adela Way, Chestertown, MD 21620
  • $585,000
  • 4Bd
  • 4Ba
  • 5,576 Sq Ft
SOLD
124 Char Nor Manor Blvd, Chestertown, MD 21620
  • $250,000
  • 2Bd
  • 2Ba
  • 1,024 Sq Ft
SOLD
2010 Mcginnes Rd, Chestertown, MD 21620
  • $354,900
  • 3Bd
  • 1Ba
  • 1,253 Sq Ft
SOLD
225 Duke Of Kent St, Chestertown, MD 21620
  • $395,000
  • 3Bd
  • 3Ba
  • 1,850 Sq Ft
SOLD
Church Hill Road, Chestertown, MD 21620
  • $162,000
  • 5.34 Acre
SOLD
8293 Brices Mill Rd, Chestertown, MD 21620
  • $775,000
  • 4Bd
  • 3Ba
  • 2,836 Sq Ft
SOLD
201 Radcliffe Dr, Chestertown, MD 21620
  • $795,000
  • 4Bd
  • 3Ba
  • 2,736 Sq Ft
SOLD
151 - 200 of 589 Homes 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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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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