High St, Winchendon, MA Property Records

Worcester County and Winchendon Town property records for 44 addresses on High St, Winchendon, MA · Last verified August 2026

High St Highlights

Properties 44
Median Sale Price $425,000
Deeds and Mortgages on File 80
Median Price per Sqft $167
Owner Occupied 91%
Median Annual Tax Bill $4,470
Median Year Built 1920
Median Ownership Tenure 9 years

Properties on High St

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

1 High St

1 ba · 49,132 sqft · built 1850 · 4 acres

Last Sale Tax Bill Prior Sale Owner Records
$125,000Dec 2017 $1,7502025 —May 2016 Owner on Record Assessor + 1 DocumentUpdated Apr 2026

5 High St

4 bd · 1.5 ba · 2,196 sqft · built 1900 · 0.239 acres

Last Sale Tax Bill Prior Sale Owner Records
$400,000Dec 2023 $4,5362025 Amount on Record Sep 2013 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

12 High St

4 bd · 3.5 ba · 6,045 sqft · built 1880 · 0.75 acres

Last Sale Tax Bill Prior Sale Owner Records
$529,900Nov 2020 $6,7142025 Amount on Record Dec 2003 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

17 High St

4 bd · 1.5 ba · 2,388 sqft · built 1907 · 0.2 acres

Last Sale Tax Bill Prior Sale Owner Records
$200,000Jul 2020 $3,1012025 —Jul 2013 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

19 High St

5 bd · 2.5 ba · 2,776 sqft · built 1850 · 0.219 acres

Last Sale Tax Bill Prior Sale Owner Records
$280,000Nov 2021 $3,7912025 Amount on Record Aug 2012 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

24 High St

5 bd · 4 ba · 4,085 sqft · built 1812 · 1.48 acres

Last Sale Tax Bill Prior Sale Owner Records
$45,000Aug 1993 $4,4702025 Amount on Record Jan 1993 2 Owners on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

25 High St

3 bd · 1.5 ba · 1,637 sqft · built 1860 · 0.226 acres

Last Sale Tax Bill Prior Sale Owner Records
$137,500Dec 2014 $3,4272025 Owner on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

31 High St

4 bd · 2 ba · 2,458 sqft · built 1920 · 0.739 acres

Last Sale Tax Bill Prior Sale Owner Records
$420,000Feb 2025 $5,5672025 Amount on Record Aug 2024 Owner on Record Owner Occupied Assessor + 10 DocumentsUpdated Jul 2026

46 High St

5 bd · 2.5 ba · 3,700 sqft · built 1898 · 1.06 acres

Last Sale Tax Bill Prior Sale Owner Records
$415,000Nov 2020 $5,4942025 Amount on Record Nov 2009 Owner on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

47 High St

3 bd · 1.5 ba · 2,051 sqft · built 1870 · 0.95 acres

Last Sale Tax Bill Prior Sale Owner Records
$140,000Dec 2002 $1,7212025 Amount on Record Jan 2000 Owner on Record Owner Occupied AssessorUpdated Jul 2026

49 High St

3 bd · 3.5 ba · 1,746 sqft · built 2024 · 0.309 acres

Last Sale Tax Bill Prior Sale Owner Records
$494,900Nov 2024 $3,1212025 Amount on Record Oct 2023 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

51 High St

2.5 ba · 1,531 sqft · built 2024 · 0.371 acres

Last Sale Tax Bill Prior Sale Owner Records
$479,900Sep 2024 $4,7812025 Amount on Record Oct 2023 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

52 High St

3 bd · 1.5 ba · 1,568 sqft · built 1994 · 3.11 acres

Last Sale Tax Bill Prior Sale Owner Records
$245,000Apr 2019 $3,8382025 Amount on Record Apr 2015 2 Owners on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

60 High St

4 bd · 2.5 ba · 1,946 sqft · built 1890 · 0.558 acres

Last Sale Tax Bill Prior Sale Owner Records
$435,000Mar 2024 $5,0572025 Amount on Record Dec 2023 Owner on Record Owner Occupied Assessor + 6 DocumentsUpdated Jul 2026

85 High St

4 bd · 1.5 ba · 1,771 sqft · built 1909 · 0.31 acres

Last Sale Tax Bill Prior Sale Owner Records
—Aug 2012 $3,0532025 Amount on Record — Owner on Record Owner Occupied AssessorUpdated Aug 2026

88 High St

4 bd · 1.5 ba · 2,536 sqft · built 1900 · 6 acres

Last Sale Tax Bill Prior Sale Owner Records
$489,000Aug 2024 $4,7052025 Amount on Record Dec 2020 2 Owners on Record Assessor + 2 DocumentsUpdated Jul 2026

89 High St

3 bd · 1 ba · 1,456 sqft · built 1909 · 0.304 acres

Last Sale Tax Bill Prior Sale Owner Records
$25,000Dec 1980 $3,1772025 2 Owners on Record Owner Occupied AssessorUpdated Jul 2026

93 High St

3 bd · 1.5 ba · 1,868 sqft · built 1850 · 0.312 acres

Last Sale Tax Bill Prior Sale Owner Records
$310,000May 2026 $3,2772025 Amount on Record Apr 2026 2 Owners on Record Owner Occupied Assessor + 4 DocumentsUpdated Jun 2026

108 High St

4 bd · 2.5 ba · 2,678 sqft · built 1898 · 0.614 acres

Last Sale Tax Bill Prior Sale Owner Records
$119,900Aug 2014 $2,8052025 Amount on Record Jan 2014 Owner on Record Owner Occupied AssessorUpdated Jul 2026

109 High St

3 bd · 1 ba · 1,680 sqft · built 1900 · 0.31 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,0252025 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

118 High St

3 bd · 1.5 ba · 2,112 sqft · built 1910 · 0.5 acres

Last Sale Tax Bill Prior Sale Owner Records
$170,000May 2016 $4,2182025 —Jan 2013 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

123 High St

4 bd · 2 ba · 1,821 sqft · built 1870 · 0.839 acres

Last Sale Tax Bill Prior Sale Owner Records
$240,000Aug 2017 $4,3952025 Amount on Record Apr 2011 Owner on Record Assessor + 1 DocumentUpdated Jul 2026

141 High St

4 bd · 3 ba · 2,806 sqft · built 1949 · 0.28 acres

Last Sale Tax Bill Prior Sale Owner Records
$92,000Nov 1996 $6,1682025 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

151 High St

3 bd · 1 ba · 1,856 sqft · built 1956 · 0.419 acres

Last Sale Tax Bill Prior Sale Owner Records
$144,000Dec 2015 $4,9012025 Amount on Record Jul 2000 Owner on Record Assessor + 3 DocumentsUpdated Jul 2026

165 High St

2 bd · 1 ba · 947 sqft · built 1948 · 0.612 acres

Last Sale Tax Bill Prior Sale Owner Records
$93,000Jul 2015 $3,3992025 Amount on Record May 2004 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

170 High St

3 bd · 1 ba · 1,428 sqft · built 1905 · 0.492 acres

Last Sale Tax Bill Prior Sale Owner Records
$82,500Sep 1990 $3,4522025 Amount on Record Jul 1987 2 Owners on Record Owner Occupied AssessorUpdated Jul 2026

177 High St

4 bd · 1.5 ba · 2,536 sqft · built 1815 · 4.03 acres

Last Sale Tax Bill Prior Sale Owner Records
$425,000May 2025 $3,2482025 Amount on Record Sep 2015 Owner on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

188 High St

2 bd · 1 ba · 922 sqft · built 1900 · 0.2 acres

Last Sale Tax Bill Prior Sale Owner Records
$37,500Sep 1983 $2,2072025 2 Owners on Record Owner Occupied AssessorUpdated Jul 2026

191 High St

3 bd · 2 ba · 2,105 sqft · built 1955 · 0.985 acres

Last Sale Tax Bill Prior Sale Owner Records
$3,9002025 Owner on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

201 High St

7 bd · 3.5 ba · 3,240 sqft · built 1955 · 2.98 acres

Last Sale Tax Bill Prior Sale Owner Records
$82,000Oct 1985 $5,2522025 2 Owners on Record Owner Occupied Assessor + 3 DocumentsUpdated Aug 2026

220 High St

4 bd · 1.5 ba · 2,413 sqft · built 1985 · 3.18 acres

Last Sale Tax Bill Prior Sale Owner Records
$12,000Nov 1984 $5,6512025 2 Owners on Record Owner Occupied AssessorUpdated Jul 2026

230 High St

3 bd · 1.5 ba · 1,816 sqft · built 1985 · 3.16 acres

Last Sale Tax Bill Prior Sale Owner Records
$5,5892025 Owner on Record Owner Occupied AssessorUpdated Jul 2026

231 High St

4 bd · 3.5 ba · 2,464 sqft · built 1985 · 1.73 acres

Last Sale Tax Bill Prior Sale Owner Records
$443,000Aug 2019 $7,3472025 Amount on Record Aug 2005 Owner on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

240 High St

2 bd · 2.5 ba · 1,459 sqft · built 2002 · 3.08 acres

Last Sale Tax Bill Prior Sale Owner Records
$45,000Mar 2002 $5,3022025 Amount on Record Jan 1992 Owner on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

261 High St

4 bd · 3 ba · 2,914 sqft · built 1985 · 1.28 acres

Last Sale Tax Bill Prior Sale Owner Records
$345,000Dec 2014 $8,2562025 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

271 High St

20 bd · 1 ba · 2,268 sqft · 0.75 acres

Last Sale Tax Bill Prior Sale Owner Records
$239,900Mar 2004 $1,2132025 Amount on Record Aug 2003 2 Owners on Record Owner Occupied AssessorUpdated Jul 2026

277 High St

4 bd · 2.5 ba · 3,052 sqft · built 2004 · 1.8 acres

Last Sale Tax Bill Prior Sale Owner Records
$469,500Nov 2021 $7,8802025 2 Owners on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

282 High St

5 bd · 3.5 ba · 3,929 sqft · built 1949 · 6.3 acres

Last Sale Tax Bill Prior Sale Owner Records
$350,000May 2020 $8,8452025 Amount on Record Oct 2002 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

285 High St

5 bd · 3.5 ba · 3,076 sqft · built 1966 · 1.28 acres

Last Sale Tax Bill Prior Sale Owner Records
$260,000Jan 2014 $5,2082025 2 Owners on Record Owner Occupied Assessor + 4 DocumentsUpdated Jul 2026

289 High St

2 bd · 2.5 ba · 2,658 sqft · built 1985 · 2.27 acres

Last Sale Tax Bill Prior Sale Owner Records
—May 2016 $5,8672025 Amount on Record Sep 1997 Owner on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

300 High St

5 bd · 3.5 ba · 5,456 sqft · built 1923 · 4 acres

Last Sale Tax Bill Prior Sale Owner Records
$173,500Dec 2019 $9,0552025 Amount on Record Dec 2015 Owner on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

350 High St

2 bd · 1 ba · 1,502 sqft · built 1948 · 3 acres

Last Sale Tax Bill Prior Sale Owner Records
$97,000Sep 1993 $3,2292025 Amount on Record Apr 1991 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

385 High St

3 bd · 1 ba · 1,166 sqft · built 1948 · 0.91 acres

Last Sale Tax Bill Prior Sale Owner Records
$3,2362025 2 Owners on Record Owner Occupied AssessorUpdated Jul 2026

386 High St

3 bd · 1.5 ba · 2,733 sqft · built 1954 · 16 acres

Last Sale Tax Bill Prior Sale Owner Records
$305,000Jul 2018 $5,1992025 —Aug 2001 2 Owners on Record Owner Occupied AssessorUpdated Jul 2026

Property Records in Nearby Streets