High St, Winchester, MA Property Records

Middlesex County and Winchester Town property records for 84 addresses on High St, Winchester, MA · Last verified August 2026

High St Highlights

Properties 84
Median Sale Price $1,650,000
Deeds and Mortgages on File 127
Median Price per Sqft $537
Owner Occupied 90%
Median Annual Tax Bill $181
Median Year Built 1958
Median Ownership Tenure 13 years

Properties on High St

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

4 High St

0.385 acres

Last Sale Tax Bill Prior Sale Owner Records
$4602025 2 Names on Record AssessorUpdated Apr 2026

8 High St

4 bd · 6 ba · 7,867 sqft · 0.603 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,500,000Jan 2015 $4302025 Amount on Record Apr 2013 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

10 High St

5 bd · 4.5 ba · 5,631 sqft · 0.473 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,200,000Jun 2014 $3542025 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

16 High St

4 bd · 2.5 ba · 3,252 sqft · 0.51 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$500,000Sep 2017 $1502025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

20 High St

5 bd · 3.5 ba · 5,221 sqft · 0.471 acres

Last Sale Tax Bill Prior Sale Owner Records
—Oct 2018 $1722025 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

21 High St

9.5 acres

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

32 High St

3 bd · 3.5 ba · 2,657 sqft · 0.344 acres

Last Sale Tax Bill Prior Sale Owner Records
$869,000Dec 2020 $1272025 Amount on Record Apr 1994 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Apr 2026

36 High St

5 bd · 4 ba · 3,482 sqft · 0.369 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,320,000May 2020 $1802025 Amount on Record Nov 1983 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

40 High St

5 bd · 2.5 ba · 2,799 sqft · 0.465 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$730,000Feb 2013 $1502025 Amount on Record Apr 2007 2 Names on Record Owner Occupied Assessor + 4 DocumentsUpdated May 2026

45 High St

4 bd · 2.5 ba · 2,735 sqft · 0.185 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$983,000Dec 2016 $1442025 Amount on Record Mar 1999 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

46 High St

4 bd · 2.5 ba · 2,434 sqft · 0.465 acres

Last Sale Tax Bill Prior Sale Owner Records
$1432025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

50 High St

4 bd · 2.5 ba · 2,878 sqft · 0.459 acres

Last Sale Tax Bill Prior Sale Owner Records
$850,000Jul 2014 $1512025 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

54 High St

2 bd · 2.5 ba · 3,611 sqft · 0.459 acres

Last Sale Tax Bill Prior Sale Owner Records
$650,000Jun 2010 $1462025 Amount on Record Jul 2008 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

58 High St

4 bd · 2 ba · 2,121 sqft · 0.459 acres

Last Sale Tax Bill Prior Sale Owner Records
$1512025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

62 High St

4 bd · 4 ba · 4,256 sqft · 0.462 acres

Last Sale Tax Bill Prior Sale Owner Records
$693,900Jun 2003 $1602025 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

63 High St

3 bd · 3 ba · 2,444 sqft · 0.232 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$375,000May 1997 $1562025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

65 High St

6 bd · 3.5 ba · 2,174 sqft · 0.229 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,440,150Jun 2026 $1342025 Amount on Record Dec 2016 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

67 High St

4 bd · 2.5 ba · 2,542 sqft · 0.229 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$310,000Jul 2021 $1252025 —Apr 2014 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

68 High St

3 bd · 2.5 ba · 3,034 sqft · 0.45 acres

Last Sale Tax Bill Prior Sale Owner Records
$850,000Dec 2011 $1812025 —Nov 2003 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

78 High St

3 bd · 3.5 ba · 3,935 sqft · 0.495 acres

Last Sale Tax Bill Prior Sale Owner Records
—Feb 2017 $1572025 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

81 High St

3 bd · 2.5 ba · 1,977 sqft · 0.229 acres

Last Sale Tax Bill Prior Sale Owner Records
$161,000Dec 1984 $12,0952025 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

85 High St

4 bd · 2.5 ba · 3,264 sqft · 0.286 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1562025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

94 High St

6 bd · 5.5 ba · 7,962 sqft · 0.971 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,289,500Aug 2017 $5092025 Amount on Record Sep 1991 2 Names on Record Owner Occupied Assessor + 4 DocumentsUpdated Apr 2026

95 High St

5 bd · 3.5 ba · 3,578 sqft · 0.353 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,060,000Oct 2009 $2142025 Amount on Record May 1991 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

99 High St

3 bd · 2.5 ba · 3,397 sqft · 0.305 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$352,000Jun 1991 $2212025 Amount on Record Jul 1987 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

101 High St

5 bd · 1.5 ba · 3,466 sqft · 0.241 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,150,000Aug 2005 $2062025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

111 High St

4 bd · 3.5 ba · 3,450 sqft · 0.224 acres

Last Sale Tax Bill Prior Sale Owner Records
$950,000Jun 2012 $1592025 Amount on Record Aug 1995 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

121 High St

6 bd · 3.5 ba · 5,575 sqft · 1.69 acres

Last Sale Tax Bill Prior Sale Owner Records
$2702025 2 Names on Record AssessorUpdated Apr 2026

129 High St

4 bd · 3.5 ba · 3,605 sqft · 1.12 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,050,000Sep 2017 $1892025 Amount on Record Oct 1998 1 Name on Record Owner Occupied Assessor + 7 DocumentsUpdated Apr 2026

135 High St

3 bd · 1 ba · 1,432 sqft · 0.354 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1142025 1 Name on Record Owner Occupied AssessorUpdated Apr 2026

139 High St

3 bd · 1.5 ba · 1,302 sqft · 0.507 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$945,000Feb 2026 $1132025 Amount on Record Nov 2021 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

147 High St

10 bd · 11 ba · 9,844 sqft · 0.935 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$810,000Mar 2004 $5522025 Amount on Record Sep 1996 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

150 High St

4 bd · 1.5 ba · 2,646 sqft · 0.354 acres

Last Sale Tax Bill Prior Sale Owner Records
$280,000Mar 1996 $1432025 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

153 High St

4 bd · 2.5 ba · 2,589 sqft · 0.559 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,650,000Jan 2025 $17,3022025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

155 High St

4 bd · 2 ba · 2,621 sqft · 0.752 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$710,000Nov 2009 $1472025 Amount on Record Jul 1996 1 Name on Record Owner Occupied AssessorUpdated Apr 2026

158 High St

3 bd · 3.5 ba · 2,286 sqft · 0.605 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1482025 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

162 High St

3 bd · 2.5 ba · 2,821 sqft · 0.376 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1372025 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated Apr 2026

165 High St

5 bd · 2.5 ba · 3,678 sqft · 0.462 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$760,000Nov 2010 $1812025 Amount on Record Oct 1991 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

166 High St

4 bd · 2.5 ba · 2,239 sqft · 0.354 acres

Last Sale Tax Bill Prior Sale Owner Records
$563,000May 2008 $1462025 Amount on Record Nov 1997 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

168 High St

4 bd · 2.5 ba · 3,408 sqft · 0.355 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,350,000Sep 2007 $2232025 Amount on Record Mar 2006 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

172 High St

5 bd · 3.5 ba · 3,219 sqft · 0.345 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,599,000Dec 2020 $2072025 Amount on Record Apr 2020 2 Names on Record Owner Occupied Assessor + 4 DocumentsUpdated Apr 2026

176 High St

3 bd · 2.5 ba · 2,477 sqft · 0.417 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$700,000Jun 2013 $1312025 1 Name on Record Owner Occupied Assessor + 5 DocumentsUpdated Apr 2026

179 High St

3 bd · 2.5 ba · 3,611 sqft · 0.458 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$56,000Jun 1977 $15,7072025 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

180 High St

3 bd · 2.5 ba · 5,654 sqft · 0.384 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$210,000Jun 1992 $2052025 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

182 High St

3 bd · 2.5 ba · 1,628 sqft · 0.37 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1182025 1 Name on Record Assessor + 2 DocumentsUpdated Aug 2026

185 High St

4 bd · 3.5 ba · 3,513 sqft · 0.529 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$590,000Jul 2001 $1672025 Amount on Record Jun 1998 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

186 High St

3 bd · 1.5 ba · 2,060 sqft · 0.378 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$130,000Jun 1996 $1352025 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

187 High St

3 bd · 3 ba · 4,986 sqft · 1.03 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$265,000Feb 1987 $2012025 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

189 High St

3 bd · 2 ba · 2,126 sqft · 0.481 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,191,000Jan 2026 $1322025 1 Name on Record Assessor + 1 DocumentUpdated Apr 2026

190 High St

2 bd · 1.5 ba · 2,598 sqft · 0.434 acres

Last Sale Tax Bill Prior Sale Owner Records
$1312025 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

191 High St

4 bd · 3.5 ba · 4,004 sqft · 0.459 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,455,000Jan 2014 $2332025 Amount on Record Apr 2004 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

195 High St

4 bd · 3.5 ba · 4,510 sqft · 0.686 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,275,000Jul 2003 $2582025 Amount on Record Oct 2002 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

196 High St

4 bd · 3.5 ba · 3,861 sqft · 0.38 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,950,000Jan 2022 $2192025 Amount on Record Jun 2021 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Apr 2026

200 High St

5 bd · 3.5 ba · 4,935 sqft · 0.37 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,560,000May 2019 $2002025 Amount on Record May 1996 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Apr 2026

204 High St

3 bd · 2.5 ba · 2,166 sqft · 0.352 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
—Nov 2016 $1312025 Amount on Record Dec 1978 1 Name on Record Owner Occupied AssessorUpdated Apr 2026

205 High St

4 bd · 6 ba · 8,327 sqft · 0.749 acres

Last Sale Tax Bill Prior Sale Owner Records
$124,000Feb 1983 $3842025 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

208 High St

3 bd · 2.5 ba · 2,862 sqft · 0.347 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$760,000Aug 2013 $1322025 Amount on Record Jan 1997 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

212 High St

3 bd · 2.5 ba · 2,178 sqft · 0.35 acres

Last Sale Tax Bill Prior Sale Owner Records
$555,000Aug 2009 $1192025 Amount on Record Jul 2003 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

222 High St

5 bd · 3.5 ba · 5,676 sqft · 0.479 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$2,860,000Aug 2023 $3082025 Amount on Record Dec 2006 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

225 High St

4 bd · 4.5 ba · 7,325 sqft · 0.511 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,750,000Jun 2011 $3422025 Amount on Record Sep 2005 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

226 High St

5 bd · 6.5 ba · 7,074 sqft · 0.732 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,550,000Apr 2019 $3552025 Amount on Record Dec 2010 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Apr 2026

231 High St

4 bd · 3.5 ba · 3,516 sqft · 0.692 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,110,000Jun 2017 $1742025 Amount on Record Jul 2013 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Apr 2026

232 High St

4 bd · 4 ba · 4,294 sqft · 0.578 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$3,000,000Sep 2024 $2702025 Amount on Record Nov 2010 2 Names on Record Owner Occupied Assessor + 4 DocumentsUpdated Apr 2026

233 High St

3 bd · 2 ba · 2,218 sqft · 0.495 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,161,000Jan 2024 $1372025 Amount on Record Jul 1981 2 Names on Record Assessor + 1 DocumentUpdated Apr 2026

237 High St

4 bd · 3.5 ba · 2,880 sqft · 0.372 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,775,000Sep 2021 $2102025 Amount on Record Sep 2020 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated Apr 2026

238 High St

5 bd · 7 ba · 6,771 sqft · 0.944 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,992,000Oct 2017 $3182025 Amount on Record Mar 2008 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

247 High St

3 bd · 4 ba · 4,078 sqft · 0.938 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1712025 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

249 High St

4 bd · 2.5 ba · 3,488 sqft · 0.584 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1572025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jun 2026

251 High St

5 bd · 5.5 ba · 7,265 sqft · 0.557 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$2,530,000Jul 2017 $3332025 Amount on Record Sep 2015 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

252 High St

3 bd · 4 ba · 5,196 sqft · 0.51 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$595,000Aug 1996 $2222025 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

255 High St

4 bd · 3.5 ba · 5,858 sqft · 0.731 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$930,000Feb 2003 $1802025 Amount on Record Jan 2003 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

256 High St

4 bd · 2.5 ba · 3,236 sqft · 0.461 acres

Last Sale Tax Bill Prior Sale Owner Records
$182,500Oct 1993 $2202025 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

257 High St

4 bd · 3 ba · 4,899 sqft · 1.67 acres

Last Sale Tax Bill Prior Sale Owner Records
$3,150,000May 2026 $26,7582025 Amount on Record May 1995 2 Names on Record Owner Occupied Assessor + 7 DocumentsUpdated Aug 2026

259 High St

5 bd · 3.5 ba · 4,412 sqft · 0.485 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,370,000Jul 2021 $2742025 Amount on Record Jun 1994 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

260 High St

4 bd · 2.5 ba · 4,072 sqft · 0.482 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$560,000Mar 1995 $21,9562025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

262 High St

5 bd · 6 ba · 7,000 sqft · 1.23 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$325,000Oct 1995 $3082025 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

263 High St

4 bd · 3.5 ba · 6,576 sqft · 1.02 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$2692025 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

264 High St

0.784 acres

Last Sale Tax Bill Prior Sale Owner Records
$265,000Sep 1997 $1102025 1 Name on Record AssessorUpdated Apr 2026

265 High St

5 bd · 4.5 ba · 6,335 sqft · 0.498 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$594,000Jul 1995 $2782025 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

268 High St

4 bd · 2.5 ba · 5,177 sqft · 0.842 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,430,000Oct 2005 $26,0962025 Amount on Record Oct 1998 1 Name on Record Owner Occupied Assessor + 4 DocumentsUpdated Apr 2026

272 High St

4 bd · 3.5 ba · 4,212 sqft · 0.81 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,650,000Mar 2020 $2432025 Amount on Record Jul 1994 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Apr 2026

276 High St

4 bd · 3.5 ba · 3,788 sqft · 0.459 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$772,500Jun 1999 $2322025 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jun 2026

280 High St

6 bd · 6 ba · 4,678 sqft · 0.522 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
—Dec 2014 $1632025 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

282 High St

5 bd · 4.5 ba · 6,503 sqft · 0.473 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$2812025 1 Name on Record AssessorUpdated Aug 2026

Property Records in Nearby Streets