Winchester Home Values and Market Report

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Active Properties
Address Beds Baths Living ft2 List Price Cost per ft2 DOM
144 Rowley St N/A 1 12,000 $1,900,000 $158 229 days
752 Lake Dr 4 3 2,129 $1,550,000 $728 115 days
752 Lake Dr 4 3 2,129 $1,550,000 $728 125 days
380 Main St N/A 5 6,200 $999,000 $161 132 days
No address N/A N/A N/A $950,000 Unknown 18 days
139 Grantville Rd 5 5 4,212 $950,000 $225 18 days
469 Platt Hill Rd 4 2 3,088 $895,000 $289 184 days
414 E Wakefield Blvd N/A N/A N/A $850,000 Unknown 59 days
119 W Wakefield Blvd 4 2 1,781 $849,900 $477 111 days
119 W Wakefield Blvd 4 2 1,781 $849,900 $477 112 days
Average: 4.2 2.9 2,857 $521,663 $233 195 days
Viewing 1 - 10 of 44
Viewing 1 - 10 of 44
Properties Under Contract
Address Beds Baths Living ft2 List Price Cost per ft2 DOM
180 Shore Dr 3 2 1,131 $749,900 $663 51 days
600 E Wakefield Blvd 2 1 1,361 $649,900 $477 81 days
237 Wallens Hill Rd 4 3 2,628 $579,900 $220 134 days
150 Oak St 11 6 5,233 $549,000 $104 195 days
441 Platt Hill Rd 5 3 3,404 $474,900 $139 158 days
77 Hubbard St 4 2 2,699 $359,900 $133 51 days
100 Norfolk Rd 4 2 2,914 $350,000 $120 47 days
1 Lake St N/A 3 4,800 $349,900 $72 134 days
166 E Lake St 3 2 1,360 $339,900 $249 17 days
50 Overlook Rd 3 1 1,488 $339,900 $228 37 days
Average: 3.6 2.2 2,153 $346,715 $219 92 days
Viewing 1 - 10 of 20
Viewing 1 - 10 of 20
Sold Properties
Address Beds Baths Living ft2 List Price Sold Price Cost per ft2 DOM Sold Date
431 W Wakefield Blvd 9 6 7,000 $1,850,000 $1,850,000 $264 170 days 9/4/26
424 E Wakefield Blvd 5 2 3,693 $1,595,000 $1,600,000 $433 57 days 6/26/26
129 E Lake St 3 4 2,699 $1,495,000 $1,475,000 $546 55 days 6/9/26
748 Lake Dr 5 4 3,584 $1,249,900 $1,250,000 $348 71 days 7/9/26
878 W Wakefield Blvd 4 3 3,330 $998,000 $1,200,000 $360 40 days 7/7/26
722 Lake Dr 3 3 1,556 $1,200,000 $1,200,000 $771 33 days 5/20/26
674 E Wakefield Blvd 3 3 2,097 $990,000 $1,050,000 $500 49 days 6/18/26
204 E Wakefield Blvd 2 2 1,472 $959,900 $960,000 $652 35 days 9/1/26
258 Perch Rock Trl 4 2 1,373 $795,000 $925,000 $673 29 days 6/4/26
43 E Lake St 4 3 2,131 $949,000 $920,000 $431 56 days 11/17/25
Average: 3.3 2.2 2,015 $394,786 $389,652 $236 97 days
Viewing 1 - 10 of 137
Viewing 1 - 10 of 137

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The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.