Sign up to stay up to date on the Chestertown Home Values!

or Create your own market report
Active Properties
Address Beds Baths Living ft2 List Price Cost per ft2 DOM
329 Union Church Rd 4 3 2,464 $568,900 $230 0 days
No address N/A N/A N/A $695,000 Unknown 1 day
7415 Wilkins Ln 3 1 936 $229,000 $244 7 days
7482 Poplar Ave 3 1 975 $275,000 $282 1 day
24775 Langford Rd 3 1 1,008 $315,000 $312 7 days
104 Lincoln Dr 3 1 960 $300,000 $312 0 days
302 S Mill St N/A N/A N/A $1,195,000 Unknown 10 days
212 Washington Ave 5 3 2,838 $675,000 $237 10 days
8184 Rock Hall Rd 4 2 2,330 $38,200,000 $16,394 13 days
302 S Mill St 2 1 806 $1,195,000 $1,482 13 days
217 Edmore Rd 3 2 1,398 $345,000 $246 4 days
22400 Great Oak Landing Rd. 4 3 2,864 $649,000 $226 18 days
7464 Shortall St 3 2 1,232 $304,000 $246 11 days
23208 Buck Neck Rd 3 3 1,650 $349,900 $212 21 days
1003 Twin Ct 3 3 2,076 $524,900 $252 19 days
123 Trafford Dr 4 3 1,804 $375,000 $207 22 days
117 N Water St Unit #3B 1 1 N/A $295,000 Unknown 20 days
115 Chester Arms Dr 3 2 1,140 $263,000 $230 7 days
101 S College Ave 2 2 1,036 $359,000 $346 17 days
7982 Radcliffe Rd 2 2 1,904 $455,000 $238 28 days
Cannon St N/A N/A N/A $450,000 Unknown 29 days
124 Wilton Rd 3 1 1,056 $299,900 $283 21 days
Cannon St N/A N/A N/A $350,000 Unknown 29 days
216 Birch Run Rd 3 3 2,176 $750,000 $344 22 days
8630 Elm Rd 5 3 1,936 $424,900 $219 27 days
109 Parma Rd 3 2 1,288 $315,000 $244 8 days
129 Trafford Dr 3 3 2,176 $480,000 $220 32 days
10540 Tonopah Rd 3 2 1,404 $269,000 $191 27 days
1010 Twin Ct 4 2 1,476 $375,000 $254 42 days
201 N Lynchburg St Unit #LOTS 4, 5, 6 & 7 N/A N/A N/A $300,000 Unknown 48 days
201 N Lynchburg St N/A N/A N/A $500,000 Unknown 48 days
8999 Orchard Dr 5 4 2,653 $824,900 $310 47 days
115 Metcalf Rd 3 2 1,280 $259,900 $203 50 days
7828 Country Club Ln 3 3 2,857 $799,000 $279 33 days
200 Manor Ave 4 2 1,242 $325,000 $261 55 days
121 Metcalf Rd 3 2 N/A $264,900 Unknown 57 days
200 High St N/A N/A N/A $2,300,000 Unknown 57 days
7680 Country Club Ln 5 4 2,639 $885,000 $335 67 days
9126 Fairlee Rd 3 2 1,216 $324,000 $266 65 days
896 Washington Ave 3 1 1,000 $325,000 $325 71 days
104 Conley Dr 3 2 1,280 $239,900 $187 85 days
104 Acorn Dr 3 3 1,900 $275,000 $144 90 days
25416 Commerce Ln N/A N/A N/A $1,100,000 Unknown 92 days
10781 Fermoy Rd 4 3 2,160 $429,900 $199 97 days
213 Byford Dr 4 2 1,277 $372,000 $291 97 days
8796 Maryland Pkwy N/A N/A N/A $1,495,000 Unknown 93 days
1906 Pondtown Rd N/A N/A N/A $110,000 Unknown 96 days
8796 Maryland Pkwy 9 7 4,776 $1,495,000 $313 93 days
956 Washington Ave 3 1 1,248 $275,000 $220 109 days
22470 Fairgale Farm Ln 4 5 4,257 $1,450,000 $340 99 days
Average: 3.4 2.6 1,986 $1,002,553 $558 146 days
Viewing 1 - 50 of 90
Viewing 1 - 50 of 90
Properties Under Contract
Address Beds Baths Living ft2 List Price Cost per ft2 DOM
249 Island Lark Way 3 3 1,420 $259,900 $183 3 days
104 Church Aly 2 2 1,058 $440,000 $415 21 days
533 Round Top Rd 4 2 1,800 $225,000 $125 10 days
240 Round Top Rd 3 2 1,132 $295,000 $260 10 days
21146 Montana Ave 2 2 1,500 $289,900 $193 13 days
8312 Broad Neck Rd 3 2 1,888 $380,000 $201 33 days
123 Heath Rd 3 2 1,792 $349,000 $194 43 days
21324 Persimmon Dr 2 1 1,232 $179,900 $146 52 days
105 N Water St Unit #2 2 2 1,011 $475,000 $469 77 days
201 River Rd 3 2 2,430 $629,900 $259 5 days
25750 Collins Ave 3 2 1,901 $448,000 $235 78 days
522 High St 2 3 1,518 $289,900 $190 103 days
214 Silver Heel Rd 4 3 1,972 $340,000 $172 124 days
240 Merganser Dr 3 2 1,120 $365,000 $325 115 days
218 Camelot Dr 5 4 2,578 $499,999 $193 253 days
611 Cannon St 2 2 920 $275,000 $298 256 days
Cromwell Clark Rd N/A N/A N/A $3,000,000 Unknown 240 days
Average: 2.9 2.2 1,579 $514,205 $241 54 days
Viewing 1 - 17 of 17
Viewing 1 - 17 of 17
Sold Properties
Address Beds Baths Living ft2 List Price Sold Price Cost per ft2 DOM Sold Date
202 Pine Street 3 1 1,341 $205,000 $222,000 $165 8 days 9/8/26
407 High Street 3 5 3,047 $798,000 $725,000 $237 51 days 9/8/26
207 Lincoln Drive 4 2 1,152 $135,000 $141,000 $122 4 days 9/3/26
222 Mount Vernon Avenue 4 2 1,656 $419,999 $433,000 $261 274 days 9/1/26
10720 Foreston Road 3 2 1,412 $309,000 $316,000 $223 32 days 9/1/26
210 N Queen Street 4 3 2,730 $735,000 $730,000 $267 8 days 9/1/26
101 S Mill Street 2 3 1,476 $515,000 $500,000 $338 37 days 9/1/26
103 Maple Avenue 4 3 4,536 $615,000 $615,000 $135 3 days 8/27/26
107 Conley Drive 3 1 1,140 $240,000 $245,000 $214 11 days 8/25/26
517 Round Top Road 3 1 1,248 $299,900 $289,000 $231 46 days 8/21/26
7903 Radcliffe Road 3 4 4,037 $625,000 $705,000 $174 4 days 8/19/26
22481 Goose Hollow Drive 3 2 1,296 $279,900 $335,320 $258 23 days 8/18/26
107 Flying Cloud Drive 5 4 2,534 $375,000 $380,000 $149 65 days 8/18/26
Preston Lane 3 3 1,949 $525,000 $525,000 $269 3 days 8/16/26
311 Devon Drive 4 3 3,504 $475,000 $465,000 $132 218 days 8/14/26
109 Cedar Street 3 3 1,397 $325,000 $318,000 $227 5 days 8/14/26
102 Flying Cloud Drive 3 3 1,896 $329,900 $324,000 $170 63 days 8/14/26
202 Royston Shores Road 4 3 2,292 $1,200,000 $1,200,000 $523 17 days 8/14/26
25440 Learman Road 3 4 3,142 $3,000,000 $3,000,000 $954 15 days 8/14/26
7989 Quaker Neck Road 5 5 4,305 $2,200,000 $1,900,000 $441 312 days 8/14/26
116 Cross Street N/A N/A N/A $109,999 $104,000 Unknown 75 days 8/13/26
Lot 9 Prestwick Drive N/A N/A N/A $185,000 $185,000 Unknown 633 days 8/10/26
1904 Pondtown Road 3 1 1,967 $265,000 $247,500 $125 53 days 8/10/26
139 Prospect Street 3 1 1,200 $198,000 $195,000 $162 95 days 7/31/26
304 Hadaway Drive 4 2 1,325 $300,000 $300,000 $226 49 days 7/30/26
7844 Chester Court 4 3 3,248 $640,000 $640,000 $197 223 days 7/29/26
21217 Texas Avenue 2 1 912 $244,500 $244,000 $267 84 days 7/27/26
521 N Kent Street 3 2 1,934 $385,000 $365,000 $188 1 day 7/22/26
100 Prospect Street 3 1 1,373 $215,000 $215,000 $156 6 days 7/21/26
10572 Watonga Road 3 2 1,404 $325,000 $325,000 $231 2 days 7/16/26
215 Fairview Drive 3 3 1,784 $425,000 $435,000 $243 5 days 7/16/26
704 Truslow Road 3 3 2,060 $440,000 $453,000 $219 23 days 7/14/26
23264 Clarissa Road 3 2 1,248 $365,000 $365,000 $292 5 days 7/13/26
221 Dutchess Road 3 2 1,130 $228,000 $228,000 $201 1 day 7/13/26
110 S Queen Street N/A N/A N/A $525,000 $541,500 Unknown 19 days 7/10/26
9816 Fairlee Road 3 3 1,624 $535,000 $535,000 $329 14 days 7/10/26
10584 Klamath Road 3 2 N/A $319,900 $320,000 Unknown 5 days 7/8/26
144 Prospect Street 2 2 1,082 $159,000 $165,000 $152 25 days 7/7/26
21363 Lynn Lane 3 1 1,314 $205,000 $205,000 $156 6 days 7/2/26
114 Chester Vw 3 2 2,064 $1,650,000 $1,650,000 $799 1 day 6/30/26
108 Pine Street 3 1 910 $115,000 $85,000 $93 44 days 6/30/26
118 Grant Court 3 2 1,664 $457,500 $460,000 $276 4 days 6/29/26
7761 Broad Neck Road 5 3 2,700 $1,500,000 $1,550,000 $574 1 day 6/29/26
23416 Cloquet Road 3 2 1,512 $384,000 $384,000 $253 7 days 6/29/26
109 S College Avenue 3 3 1,216 $419,900 $410,000 $337 72 days 6/26/26
1014 Twin Court 3 2 1,817 $499,000 $525,000 $288 1 day 6/26/26
231 Richard Drive 5 3 2,956 $1,150,000 $1,050,000 $355 87 days 6/26/26
423 Calvert Street 3 2 1,136 $185,000 $190,000 $167 10 days 6/26/26
8629 Airy Hill Road 3 2 1,440 $425,000 $395,000 $274 9 days 6/25/26
205 River Road 4 3 2,877 $869,900 $855,000 $297 7 days 6/24/26
Average: 3.2 2.3 1,851 $462,233 $456,018 $244 52 days
Viewing 1 - 50 of 106
Viewing 1 - 50 of 106