Winter St, Weston, MA Property Records

Middlesex County and Weston Town property records for 41 addresses on Winter St, Weston, MA · Last verified August 2026

Winter St Highlights

Properties 41
Median Sale Price $1,850,000
Deeds and Mortgages on File 61
Median Price per Sqft $662
Owner Occupied 83%
Median Annual Tax Bill $15,877
Median Year Built 1960
Median Ownership Tenure 10 years

Properties on Winter St

Owner names and prior sale amounts shown locked below are available instantly with a free trial.

3 Winter St

4 bd · 2 ba · 2,933 sqft · 1.55 acres

Last Sale Tax Bill Prior Sale Owner Records
—Mar 2018 $14,1562025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

10 Winter St

4 bd · 2.5 ba · 2,452 sqft · 1.19 acres

Last Sale Tax Bill Prior Sale Owner Records
$423,200Mar 1997 $13,8552025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

15 Winter St

3 bd · 2 ba · 1,728 sqft · 1.9 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
—Jun 2013 $11,4532025 1 Name on Record AssessorUpdated Jul 2026

21 Winter St

5 bd · 2.5 ba · 2,736 sqft · 1.51 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,045,000Dec 2024 $12,5642025 Amount on Record Aug 1993 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

27 Winter St

4 bd · 2.5 ba · 3,050 sqft · 1.39 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,307,500Jul 2016 $15,6652025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

32 Winter St

5 bd · 5 ba · 5,748 sqft · 1.39 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,400,000Feb 2014 $34,1772025 Amount on Record Oct 2009 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

33 Winter St

3 bd · 2.5 ba · 2,206 sqft · 1.38 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,500,000Aug 2025 $11,4152025 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

40 Winter St

4 bd · 3.5 ba · 2,673 sqft · 1.64 acres

Last Sale Tax Bill Prior Sale Owner Records
$390,000Aug 1993 $21,1322025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

41 Winter St

5 bd · 5.5 ba · 4,210 sqft · 1.98 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,234,000Oct 2014 $19,4762025 Amount on Record Nov 2003 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

100 Winter St

12,916 sqft · Built 1995 · 4.29 acres

Last Sale Tax Bill Prior Sale Owner Records
1 Name on Record AssessorUpdated Apr 2026

154 Winter St

4 bd · 2.5 ba · 1,940 sqft · 4.08 acres

Last Sale Tax Bill Prior Sale Owner Records
$832,500Dec 2018 $11,1992025 1 Name on Record Owner Occupied Assessor + 6 DocumentsUpdated Jul 2026

161 Winter St

3 bd · 3 ba · 3,074 sqft · 1.79 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,000,000Jul 2016 $13,5822025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

162 Winter St

5 bd · 4.5 ba · 3,771 sqft · 0.229 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,498,000May 2023 $26,7842025 Amount on Record Aug 2021 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

170 Winter St

3 bd · 2.5 ba · 2,288 sqft · 2.35 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,364,500Jan 2020 $16,5652025 Amount on Record Apr 2005 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

181 Winter St

5 bd · 3.5 ba · 3,034 sqft · 2.16 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,600,000Mar 2024 $15,6202026 Amount on Record Apr 2010 2 Names on Record Assessor + 2 DocumentsUpdated Aug 2026

185 Winter St

4 bd · 4 ba · 4,339 sqft · 2.06 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,100,000Dec 2020 $27,4532025 Amount on Record Jul 2003 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

199 Winter St

5 bd · 5.5 ba · 4,764 sqft · 1.39 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,500,000Oct 2021 $30,9722025 —Feb 2015 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

202 Winter St

3 bd · 3.5 ba · 2,056 sqft · 1.46 acres

Last Sale Tax Bill Prior Sale Owner Records
$815,000Mar 2015 $11,8292025 Amount on Record Jul 1989 1 Name on Record Owner Occupied Assessor + 4 DocumentsUpdated Jul 2026

205 Winter St

4 bd · 2.5 ba · 2,707 sqft · 4.22 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$15,1262025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

214 Winter St

3 bd · 3.5 ba · 1,690 sqft · 1.6 acres

Last Sale Tax Bill Prior Sale Owner Records
$417,000Feb 1996 $12,2002025 Amount on Record Sep 1988 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

215 Winter St

4 bd · 4.5 ba · 4,192 sqft · 1.87 acres

Last Sale Tax Bill Prior Sale Owner Records
$500,000Nov 1997 $17,8902025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

225 Winter St

5 bd · 5.5 ba · 5,058 sqft · 7.39 acres

Last Sale Tax Bill Prior Sale Owner Records
$970,000May 2022 $37,5272025 —Apr 2022 1 Name on Record Owner Occupied Assessor + 4 DocumentsUpdated Jul 2026

226 Winter St

4 bd · 3 ba · 2,132 sqft · 1.57 acres

Last Sale Tax Bill Prior Sale Owner Records
$880,000May 2010 $14,1812025 Amount on Record Sep 1999 2 Names on Record Owner Occupied Assessor + 4 DocumentsUpdated Aug 2026

231 Winter St

5 bd · 4.5 ba · 4,877 sqft · 8.87 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,605,000May 2017 $23,4952025 —Sep 2016 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

234 Winter St

4 bd · 3.5 ba · 1,780 sqft · 1.42 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,299,000Sep 2021 $15,0432025 —Jan 2017 1 Name on Record Owner Occupied Assessor + 4 DocumentsUpdated Jul 2026

239 Winter St

5 bd · 3.5 ba · 3,933 sqft · 1.99 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,000,000Apr 2010 $15,8772025 Amount on Record Jul 2008 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

242 Winter St

4 bd · 3.5 ba · 3,106 sqft · 1.42 acres

Last Sale Tax Bill Prior Sale Owner Records
$15,7122025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

245 Winter St

6 bd · 7 ba · 6,138 sqft · 1.49 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$2,250,000Aug 2018 $33,6982025 Amount on Record Feb 2018 1 Name on Record Owner Occupied Assessor + 5 DocumentsUpdated Jul 2026

250 Winter St

3 bd · 3.5 ba · 2,348 sqft · 1.64 acres

Last Sale Tax Bill Prior Sale Owner Records
$14,0032025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

257 Winter St

4 bd · 3.5 ba · 4,734 sqft · 3.05 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,050,000Jul 1998 $23,3072025 Amount on Record Jul 1996 1 Name on Record AssessorUpdated Jul 2026

262 Winter St

5 bd · 6.5 ba · 6,911 sqft · 1.64 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,875,000Mar 2012 $41,9792025 Amount on Record Feb 1997 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

270 Winter St

5 bd · 3 ba · 2,360 sqft · 0.139 acres

Last Sale Tax Bill Prior Sale Owner Records
$14,8342025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

285 Winter St

4 bd · 4 ba · 3,466 sqft · 1.67 acres

Last Sale Tax Bill Prior Sale Owner Records
$965,000May 2012 $15,9252025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

292 Winter St

4 bd · 3.5 ba · 3,480 sqft · 1.94 acres

Last Sale Tax Bill Prior Sale Owner Records
$16,3532025 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

314 Winter St

5 bd · 3.5 ba · 3,262 sqft · 3.74 acres

Last Sale Tax Bill Prior Sale Owner Records
$989,500Jan 1998 $19,5922025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

324 Winter St

4 bd · 4.5 ba · 3,042 sqft · 2.37 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,050,000May 2012 $16,4402025 Amount on Record Jul 1991 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

333 Winter St

75,625 sqft · Built 2001 · 23.2 acres

Last Sale Tax Bill Prior Sale Owner Records
1 Name on Record AssessorUpdated Apr 2026

342 Winter St

5 bd · 3.5 ba · 3,181 sqft · 0.93 acres

Last Sale Tax Bill Prior Sale Owner Records
1 Name on Record AssessorUpdated Apr 2026

352 Winter St

5 bd · 6 ba · 5,654 sqft · 0.95 acres

Last Sale Tax Bill Prior Sale Owner Records
1 Name on Record AssessorUpdated Apr 2026

372 Winter St

4 bd · 2.5 ba · 3,044 sqft · 1.69 acres

Last Sale Tax Bill Prior Sale Owner Records
$870,000May 2009 $14,8062025 Amount on Record Jan 1995 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

380 Winter St

4 bd · 2.5 ba · 1,850 sqft · 1.58 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,850,000Oct 2022 $19,2862025 Amount on Record Jun 2002 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

Property Records in Nearby Streets