Chestertown Home Values and Market Report

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Address Beds Baths Living ft2 List Price Cost per ft2 DOM
200 High St N/A N/A N/A $2,300,000 Unknown 23 days
117 Water St N Unit #1A, 1B, 2A, & 2B 7 5 5,400 $1,500,000 $277 159 days
8796 Maryland Pkwy N/A N/A N/A $1,495,000 Unknown 59 days
8796 Maryland Pkwy 9 7 4,776 $1,495,000 $313 59 days
Little Harbor Way Unit #1 3 3 2,231 $1,459,000 $653 270 days
22470 Fairgale Farm Ln 4 5 4,257 $1,450,000 $340 65 days
327 Cannon St N/A N/A N/A $1,300,000 Unknown 123 days
105 High St 5 5 3,243 $1,245,500 $384 274 days
25416 Commerce Ln N/A N/A N/A $1,100,000 Unknown 58 days
#25 Landing Ln 4 4 2,784 $1,099,900 $395 246 days
Average: 3.3 2.7 2,041 $424,177 $275 240 days
Viewing 1 - 10 of 102
Viewing 1 - 10 of 102
Address Beds Baths Living ft2 List Price Cost per ft2 DOM
25440 Learman Rd 3 4 3,142 $3,000,000 $954 64 days
Cromwell Clark Rd N/A N/A N/A $3,000,000 Unknown 240 days
7989 Quaker Neck Rd 5 5 4,305 $2,200,000 $511 313 days
7828 Country Club Ln 3 3 2,857 $799,000 $279 6 days
407 High St 3 5 3,047 $798,000 $261 51 days
210 N Queen St 4 3 2,730 $735,000 $269 21 days
103 Maple Ave 4 3 4,536 $615,000 $135 41 days
Preston Lane 3 3 1,949 $525,000 $269 3 days
101 S Mill St 2 3 1,476 $515,000 $348 49 days
105 N Water St Unit #2 2 2 1,011 $475,000 $469 43 days
Average: 3.3 3.0 2,255 $679,862 $289 165 days
Viewing 1 - 10 of 24
Viewing 1 - 10 of 24
Address Beds Baths Living ft2 List Price Sold Price Cost per ft2 DOM Sold Date
23620 Lands End Road 5 8 9,852 $4,850,000 $4,221,800 $428 128 days 11/24/25
10121 Fairlee Road 6 5 4,954 $2,350,000 $2,100,000 $423 60 days 2/2/26
7761 Broad Neck Road 5 3 2,700 $1,500,000 $1,550,000 $574 1 day 6/29/26
7961 Quaker Neck Road 5 4 4,167 $1,550,000 $1,550,000 $371 87 days 11/7/25
10800 Cliff Road 5 4 5,241 $1,495,000 $1,524,900 $290 7 days 2/17/26
21082 Wyoming Avenue 3 4 2,699 $1,550,000 $1,350,000 $500 105 days 9/22/25
860 & 870 High Street N/A N/A N/A $375,000 $1,236,000 Unknown 611 days 1/16/26
119 High Street 5 5 4,409 $1,250,000 $1,165,000 $264 6 days 12/1/25
23393 Cacaway Farm Lane 3 4 4,446 $1,195,000 $1,150,000 $258 364 days 12/10/25
120 Speer Road N/A N/A N/A $1,250,000 $1,100,000 Unknown 230 days 12/22/25
Average: 3.2 2.4 1,955 $484,602 $472,076 $242 81 days
Viewing 1 - 10 of 149
Viewing 1 - 10 of 149