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Kent County Middle School Zone Homes For Sale | Page 2

262 Homes
 
115 Chester Arms Dr, Chestertown, MD 21620
  • $259,000
  • 3Bd
  • 2Ba
  • 1,140 Sq Ft
$4K
21191 W Sharp St, Rock Hall, MD 21661
  • $610,000
  • 3Bd
  • 3Ba
  • 1,700 Sq Ft
Open SAT 10-2
101 S College Ave, Chestertown, MD 21620
  • $359,000
  • 2Bd
  • 2Ba
  • 1,036 Sq Ft
$10K
1003 Twin Ct, Chestertown, MD 21620
  • $499,900
  • 3Bd
  • 3Ba
  • 2,076 Sq Ft
$25K
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
216 Birch Run Rd, Chestertown, MD 21620
  • $750,000
  • 3Bd
  • 3Ba
  • 2,176 Sq Ft
13831 Augustine Herman Hwy, Galena, MD 21635
  • $369,900
  • 3Bd
  • 3Ba
  • 2,343 Sq Ft
16 Howell Point Rd, Betterton, MD 21610
  • $487,000
  • 3Bd
  • 3Ba
  • 1,948 Sq Ft
$8K
7982 Radcliffe Rd, Chestertown, MD 21620
  • $399,000
  • 2Bd
  • 2Ba
  • 1,904 Sq Ft
$56K
8630 Elm Rd, Chestertown, MD 21620
  • $424,900
  • 5Bd
  • 3Ba
  • 1,936 Sq Ft
$20.1K
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
25133 Smithville Rd, Worton, MD 21678
  • $357,997
  • 4Bd
  • 3Ba
  • 2,208 Sq Ft
$2K
Cannon Street, Chestertown, MD 21620
  • $196,000
  • 0.22 Acre
$154K
620 Cannon St, Chestertown, MD 21620
  • $85,000
  • 0.07 Acre
$14.9K
12118 Still Pond Creek Rd, Worton, MD 21678
  • $585,000
  • 4Bd
  • 3Ba
  • 2,322 Sq Ft
129 Trafford Dr, Chestertown, MD 21620
  • $480,000
  • 3Bd
  • 3Ba
  • 3,176 Sq Ft
5862 N Main St, Rock Hall, MD 21661
  • $345,000
  • 3Bd
  • 2Ba
  • 1,381 Sq Ft
$4K
11960 Flour Mill St, Kennedyville, MD 21645
  • $515,000
  • 7Bd
  • 5Ba
  • 3,836 Sq Ft
32745 Hunt Ln, Galena, MD 21635
  • $725,000
  • 3Bd
  • 2Ba
  • 1,120 Sq Ft
20714 Wilkins Ave, Rock Hall, MD 21661
  • $575,000
  • 3Bd
  • 3Ba
  • 1,920 Sq Ft
$24.9K
21352 Allens Ln, Rock Hall, MD 21661
  • $330,000
  • 2Bd
  • 2Ba
  • 1,710 Sq Ft
21610 Hidden Creek Dr, Rock Hall, MD 21661
  • $699,000
  • 4Bd
  • 3Ba
  • 2,185 Sq Ft
1010 Twin Ct, Chestertown, MD 21620
  • $349,900
  • 4Bd
  • 2Ba
  • 1,476 Sq Ft
$15.1K
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 TUE 6-7
14046 Tockwogh Ln, Galena, MD 21635
  • $1,595,000
  • 4Bd
  • 2Ba
  • 2,538 Sq Ft
200 Manor Ave, Chestertown, MD 21620
  • $325,000
  • 4Bd
  • 2Ba
  • 2,198 Sq Ft
12555 Coopers Ln, Worton, MD 21678
  • $1,395,000
  • 4Bd
  • 3Ba
  • 3,626 Sq Ft
Open SAT 12-2
305 Roosevelt Dr, Chestertown, MD 21620
  • $45,000
  • 0.61 Acre
$15K
121 Metcalf Rd, Chestertown, MD 21620
  • $264,900
  • 3Bd
  • 2Ba
10520 Worton Rd, Worton, MD 21678
  • $100,000
  • 3Bd
  • 1Ba
  • 1,896 Sq Ft
$25K
10540 Worton Rd, Worton, MD 21678
  • $90,000
  • 3Bd
  • 1Ba
  • 1,056 Sq Ft
$35K
316 Middle St, Millington, MD 21651
  • $25,000
  • —Bd
  • —Ba
  • 672 Sq Ft
25124 E Kentfield Rd, Worton, MD 21678
  • $565,000
  • 3Bd
  • 3Ba
  • 2,187 Sq Ft
21251 Chesapeake Ave, Rock Hall, MD 21661
  • $480,000
  • 5Bd
  • 2Ba
  • 1,664 Sq Ft
5804 Downey Ave, Rock Hall, MD 21661
  • $199,000
  • —Bd
  • —Ba
  • 5,558 Sq Ft
$26K
25028 Heather Ln, Worton, MD 21678
  • $90,000
  • 3Bd
  • 2Ba
  • 1,424 Sq Ft
$50K
5666 Walnut St, Rock Hall, MD 21661
  • $550,000
  • 3Bd
  • 2Ba
  • 1,296 Sq Ft
$49K
Photos coming soon
  • $289,000
  • —Bd
  • —Ba
321 West St, Millington, MD 21651
  • $334,900
  • 3Bd
  • 2Ba
  • 1,366 Sq Ft
$5K
5738 Beach Rd, Rock Hall, MD 21661
  • $699,900
  • 0.96 Acre
$50.1K
7680 Country Club Ln, Chestertown, MD 21620
  • $825,000
  • 5Bd
  • 4Ba
  • 2,639 Sq Ft
$60K
31923 River Park Rd, Millington, MD 21651
  • $435,000
  • 3Bd
  • 2Ba
  • 1,160 Sq Ft
9126 Fairlee Rd, Chestertown, MD 21620
  • $314,000
  • 3Bd
  • 2Ba
  • 1,216 Sq Ft
$10K
Photos coming soon
  • $195,000
  • 15 Acre
896 Washington Ave, Chestertown, MD 21620
  • $325,000
  • 3Bd
  • 1Ba
  • 1,000 Sq Ft
5686 S Main St, Rock Hall, MD 21661
  • $375,000
  • 3Bd
  • 2Ba
  • 1,326 Sq Ft
21232 Rock Hall Ave, Rock Hall, MD 21661
  • $318,000
  • 2Bd
  • 2Ba
  • 1,200 Sq Ft
$2K
51 - 100 of 262 Homes for sale in Chestertown, MD
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Chestertown, MD real estate market trends

Statistics as of October 2026
$392K
Avg. list price
$247/Sqft
Avg. price/sqft
84
Homes for sale
1,964 Sqft
Avg. home size
116 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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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: 10/1/2026. 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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