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Homes Recently Sold in Chestertown, MD | Page 3

589 Homes
 
136 Hilltop Dr, Chestertown, MD 21620
  • $376,000
  • 3Bd
  • 2Ba
  • 1,432 Sq Ft
SOLD 05/19/26
10087 John Carvill Rd, Chestertown, MD 21620
  • $695,000
  • 3Bd
  • 2Ba
  • 1,566 Sq Ft
SOLD 05/18/26
107 Metcalf Rd, Chestertown, MD 21620
  • $259,900
  • 3Bd
  • 2Ba
  • 1,200 Sq Ft
SOLD 05/18/26
23698 L Rd, Chestertown, MD 21620
  • $15,000
  • 2.6 Acre
SOLD 05/15/26
107 Longfellow Dr, Chestertown, MD 21620
  • $278,500
  • 3Bd
  • 1Ba
SOLD
132 Prospect St, Chestertown, MD 21620
  • $155,000
  • 2Bd
  • 1Ba
  • 910 Sq Ft
SOLD
100 Adela Way, Chestertown, MD 21620
  • $490,000
  • 4Bd
  • 4Ba
  • 3,799 Sq Ft
SOLD
101 Pine Tree Rd, Chestertown, MD 21620
  • $480,000
  • 4Bd
  • 2Ba
  • 1,848 Sq Ft
SOLD
217 Philosophers Ter, Chestertown, MD 21620
  • $370,000
  • 3Bd
  • 2Ba
  • 1,404 Sq Ft
SOLD
206 S Water St, Chestertown, MD 21620
  • $545,000
  • 4Bd
  • 3Ba
  • 2,008 Sq Ft
SOLD
144 Char Nor Manor Blvd, Chestertown, MD 21620
  • $50,000
  • 0.52 Acre
SOLD
103 Flying Cloud Dr, Chestertown, MD 21620
  • $339,900
  • 3Bd
  • 3Ba
  • 1,724 Sq Ft
SOLD
11040 Kylie Ln, Chestertown, MD 21620
  • $620,000
  • 4Bd
  • 4Ba
  • 3,684 Sq Ft
SOLD
515 N Kent St, Chestertown, MD 21620
  • $495,000
  • 4Bd
  • 3Ba
  • 2,220 Sq Ft
SOLD
104 Garland Ave, Chestertown, MD 21620
  • $480,000
  • 3Bd
  • 2Ba
  • 1,734 Sq Ft
SOLD
148 Step Rd, Chestertown, MD 21620
  • $365,000
  • 4Bd
  • 2Ba
  • 1,400 Sq Ft
SOLD
201 Greenwood Ave, Chestertown, MD 21620
  • $495,000
  • 4Bd
  • 3Ba
  • 3,984 Sq Ft
SOLD
216 Blakefield Dr, Chestertown, MD 21620
  • $552,000
  • 4Bd
  • 3Ba
  • 2,400 Sq Ft
SOLD
513 Round Top Rd, Chestertown, MD 21620
  • $220,000
  • 4Bd
  • 1Ba
  • 1,248 Sq Ft
SOLD
6 Byford Ct, Chestertown, MD 21620
  • $749,500
  • 3Bd
  • 3Ba
  • 3,136 Sq Ft
SOLD
206 Camelot Dr, Chestertown, MD 21620
  • $455,000
  • 4Bd
  • 4Ba
  • 2,186 Sq Ft
SOLD
23055 Old Fairlee Rd, Chestertown, MD 21620
  • $332,000
  • 3Bd
  • 2Ba
  • 1,628 Sq Ft
SOLD
112 Metcalf Rd, Chestertown, MD 21620
  • $250,000
  • 3Bd
  • 2Ba
  • 1,280 Sq Ft
SOLD
206 Flyway Ln, Chestertown, MD 21620
  • $512,500
  • 4Bd
  • 4Ba
  • 3,000 Sq Ft
SOLD
8750 Georgetown Rd, Chestertown, MD 21620
  • $334,000
  • 3Bd
  • 2Ba
  • 1,900 Sq Ft
SOLD
23110 Old Fairlee Rd, Chestertown, MD 21620
  • $330,000
  • 3Bd
  • 1Ba
  • 1,805 Sq Ft
SOLD
107 Oak Leaf Dr, Chestertown, MD 21620
  • $295,000
  • 3Bd
  • 3Ba
  • 1,947 Sq Ft
SOLD
129 Parma Rd, Chestertown, MD 21620
  • $330,000
  • 3Bd
  • 2Ba
  • 1,170 Sq Ft
SOLD
9925 Flatland Rd, Chestertown, MD 21620
  • $180,000
  • 3Bd
  • 2Ba
  • 1,368 Sq Ft
SOLD
105 Pearl Creek Ln, Chestertown, MD 21620
  • $459,000
  • 3Bd
  • 3Ba
  • 1,961 Sq Ft
SOLD
10751 Millbrook Dr, Chestertown, MD 21620
  • $350,000
  • 3Bd
  • 2Ba
  • 1,942 Sq Ft
SOLD
Elm Road, Chestertown, MD 21620
  • $13,000
  • 0.09 Acre
SOLD
Elm Road, Chestertown, MD 21620
  • $35,000
  • 0.33 Acre
SOLD
204 Rolling Rd, Chestertown, MD 21620
  • $340,000
  • 3Bd
  • 2Ba
  • 2,296 Sq Ft
SOLD
119 Darden Rd, Chestertown, MD 21620
  • $270,000
  • 3Bd
  • 2Ba
  • 1,424 Sq Ft
SOLD
121 Primrose Rd, Chestertown, MD 21620
  • $325,000
  • 3Bd
  • 3Ba
  • 2,034 Sq Ft
SOLD
200 Washington Ave, Chestertown, MD 21620
  • $650,000
  • 4Bd
  • 4Ba
  • 2,917 Sq Ft
SOLD
23069 Raleigh Rd, Chestertown, MD 21620
  • $175,000
  • 2Bd
  • —Ba
  • 1,160 Sq Ft
SOLD
213 Central Dr, Chestertown, MD 21620
  • $317,000
  • 3Bd
  • 2Ba
  • 1,232 Sq Ft
SOLD
21111 Texas Ave, Chestertown, MD 21620
  • $350,000
  • 3Bd
  • 2Ba
  • 1,680 Sq Ft
SOLD
Hoffecker Road, Chestertown, MD 21620
  • $190,000
  • 10.05 Acre
SOLD
109 Water St, Chestertown, MD 21620
  • $650,000
  • 4Bd
  • 2Ba
  • 2,064 Sq Ft
SOLD
141 Prospect St, Chestertown, MD 21620
  • $120,000
  • 4Bd
  • 2Ba
  • 1,156 Sq Ft
SOLD
108 Flying Cloud Dr, Chestertown, MD 21620
  • $364,900
  • 4Bd
  • 3Ba
  • 1,936 Sq Ft
SOLD
4671 Cliffs City Rd, Chestertown, MD 21620
  • $800,000
  • 3Bd
  • 2Ba
  • 1,783 Sq Ft
SOLD
24339 Chestertown Rd, Chestertown, MD 21620
  • $270,000
  • 3Bd
  • 1Ba
  • 960 Sq Ft
SOLD
Caulks Field Road, Chestertown, MD 21620
  • $11,000
  • 2 Acre
SOLD
134 Char Nor Manor Blvd, Chestertown, MD 21620
  • $260,000
  • 3Bd
  • 1Ba
  • 1,128 Sq Ft
SOLD
10800 Cliff Rd, Chestertown, MD 21620
  • $1,524,900
  • 5Bd
  • 4Ba
  • 5,241 Sq Ft
SOLD
21316 Persimmon Dr, Chestertown, MD 21620
  • $160,000
  • 2Bd
  • 1Ba
  • 1,232 Sq Ft
SOLD
101 - 150 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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