Oak St, Winchendon, MA Property Records

Worcester County and Winchendon Town property records for 15 addresses on Oak St, Winchendon, MA · Last verified October 2026

Oak St Highlights

Properties 15
Median Sale Price $282,500
Deeds and Mortgages on File 25
Median Price per Sqft $146
Owner Occupied 67%
Median Annual Tax Bill $3,697
Median Year Built 1900
Median Ownership Tenure 7 years

Properties on Oak St

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

14 Oak St

3 bd · 2 ba · 2,198 sqft · built 1922 · 0.187 acres

Last Sale Tax Bill Prior Sale Owner Records
$172,000Jan 2017 $3,5072025 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

15 Oak St, #17

5 bd · 4 ba · 3,744 sqft · built 1859 · 0.63 acres

Last Sale Tax Bill Prior Sale Owner Records
$549,900Oct 2025 $5,5942025 —Dec 2015 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Sep 2026

18 Oak St

3 bd · 1 ba · 1,744 sqft · built 1920 · 0.125 acres

Last Sale Tax Bill Prior Sale Owner Records
$176,000Jun 2007 $3,6272025 Amount on Record Feb 2004 Owner on Record Owner Occupied Assessor + 2 DocumentsUpdated Oct 2026

22 Oak St

4 bd · 1.5 ba · 2,820 sqft · built 1887 · 0.2 acres

Last Sale Tax Bill Prior Sale Owner Records
$265,000Jan 2021 $3,6972025 Amount on Record Jun 2017 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Sep 2026

33 Oak St

9 bd · 3 ba · 3,199 sqft · built 1930 · 0.38 acres

Last Sale Tax Bill Prior Sale Owner Records
$405,200Nov 1974 Owner on Record AssessorUpdated Apr 2026

45 Oak St

2 bd · 2 ba · 2,864 sqft · built 1956 · 0.43 acres

Last Sale Tax Bill Prior Sale Owner Records
$200,000Apr 2003 $3,9232025 Owner on Record AssessorUpdated Jul 2026

60 Oak St

4 bd · 1.5 ba · 2,356 sqft · built 1971 · 0.26 acres

Last Sale Tax Bill Prior Sale Owner Records
$280,000Jun 2024 $4,0582025 Amount on Record Oct 2012 Owner on Record Owner Occupied AssessorUpdated Sep 2026

88 Oak St

3 bd · 2 ba · 1,801 sqft · built 1900 · 0.2 acres

Last Sale Tax Bill Prior Sale Owner Records
$270,000Sep 2021 $3,3902025 Amount on Record May 2010 Owner on Record Assessor + 3 DocumentsUpdated Sep 2026

92 Oak St

3 bd · 1.5 ba · 1,122 sqft · built 1890 · 0.31 acres

Last Sale Tax Bill Prior Sale Owner Records
$282,500Oct 2021 $3,1982025 Amount on Record Jan 2017 2 Owners on Record Owner Occupied Assessor + 4 DocumentsUpdated Jul 2026

99 Oak St

8 bd · 5 ba · 3,621 sqft · built 1900 · 0.15 acres

Last Sale Tax Bill Prior Sale Owner Records
$300,000Jan 2024 $3,8672025 Amount on Record Apr 2005 Owner on Record Assessor + 1 DocumentUpdated Oct 2026

105 Oak St

5 bd · 3 ba · 2,906 sqft · built 1900 · 0.275 acres

Last Sale Tax Bill Prior Sale Owner Records
$430,000Jun 2025 $5,0562025 Amount on Record Jul 2020 2 Owners on Record Owner Occupied Assessor + 3 DocumentsUpdated Sep 2026

113 Oak St

8 bd · 2 ba · 3,091 sqft · built 1900 · 0.25 acres

Last Sale Tax Bill Prior Sale Owner Records
$139,000Jan 2019 $2,8472025 Amount on Record Aug 2011 2 Owners on Record Owner Occupied Assessor + 3 DocumentsUpdated Oct 2026

114 Oak St

5 bd · 1.5 ba · 2,370 sqft · built 1880 · 0.969 acres

Last Sale Tax Bill Prior Sale Owner Records
$169,900Mar 2000 $3,7592025 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

131 Oak St

4 bd · 2 ba · 2,655 sqft · built 1860 · 0.282 acres

Last Sale Tax Bill Prior Sale Owner Records
$186,000May 2019 $2,4982025 Amount on Record Sep 2016 Owner on Record Owner Occupied Assessor + 4 DocumentsUpdated Oct 2026

133 Oak St

2 bd · 1 ba · 864 sqft · built 1970 · 0.18 acres

Last Sale Tax Bill Prior Sale Owner Records
$62,000Jul 1997 $2,4092025 2 Owners on Record AssessorUpdated Jul 2026

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