Benjamin St, Winchendon, MA Property Records

Worcester County and Winchendon Town property records for 38 addresses on Benjamin St, Winchendon, MA · Last verified August 2026

Benjamin St Highlights

Properties 38
Median Sale Price $299,000
Deeds and Mortgages on File 48
Median Price per Sqft $199
Owner Occupied 89%
Median Annual Tax Bill $3,819
Median Year Built 1971
Median Ownership Tenure 9 years

Properties on Benjamin St

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

5 Benjamin St

8 bd · 4 ba · 4,610 sqft · 0.73 acres

Last Sale Tax Bill Prior Sale Owner Records
$3,5052025 1 Name on Record AssessorUpdated Apr 2026

13 Benjamin St

3 bd · 1 ba · 1,609 sqft · 0.126 acres

Last Sale Tax Bill Prior Sale Owner Records
$60,000Dec 2022 $1,8332025 Amount on Record Dec 2021 2 Names on Record Assessor + 3 DocumentsUpdated Jul 2026

14 Benjamin St

2 bd · 1.5 ba · 1,224 sqft · 0.18 acres

Last Sale Tax Bill Prior Sale Owner Records
$168,000Dec 2020 $2,1602025 Amount on Record Apr 2005 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

17 Benjamin St, #19

3 bd · 1 ba · 2,448 sqft · 0.189 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,0702025 2 Names on Record AssessorUpdated Jul 2026

49 Benjamin St

3 bd · 1.5 ba · 1,496 sqft · 0.631 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$299,000Dec 2023 $3,2942025 Amount on Record Apr 2017 1 Name on Record Owner Occupied Assessor + 6 DocumentsUpdated Jul 2026

53 Benjamin St

3 bd · 1.5 ba · 1,536 sqft · 1.02 acres

Last Sale Tax Bill Prior Sale Owner Records
$259,000Oct 2019 $4,0382025 Amount on Record Nov 2003 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

58 Benjamin St

2 bd · 1 ba · 1,441 sqft · 0.369 acres

Last Sale Tax Bill Prior Sale Owner Records
$200,000Feb 2023 $2,5962025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

66 Benjamin St

3 bd · 1 ba · 1,120 sqft · 0.439 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,1142025 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

80 Benjamin St

3 bd · 1 ba · 1,064 sqft · 0.439 acres

Last Sale Tax Bill Prior Sale Owner Records
$167,900Dec 2004 $2,2632025 Amount on Record Mar 2002 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

81 Benjamin St

3 bd · 1.5 ba · 1,536 sqft · 1.09 acres

Last Sale Tax Bill Prior Sale Owner Records
$240,000Mar 2019 $4,0202025 Amount on Record Sep 2018 1 Name on Record Owner Occupied Assessor + 5 DocumentsUpdated Jul 2026

88 Benjamin St

3 bd · 1 ba · 1,081 sqft · 0.437 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$139,900Oct 2017 $2,3092025 Amount on Record Apr 2013 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

91 Benjamin St

3 bd · 2 ba · 1,536 sqft · 1.56 acres

Last Sale Tax Bill Prior Sale Owner Records
$194,900Jul 2004 $3,8352025 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

92 Benjamin St

3 bd · 1.5 ba · 1,296 sqft · 0.4 acres

Last Sale Tax Bill Prior Sale Owner Records
$99,000Jun 1987 $3,8022025 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

105 Benjamin St

3 bd · 1.5 ba · 954 sqft · 0.25 acres

Last Sale Tax Bill Prior Sale Owner Records
$15,000Oct 2002 $2,8982025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

111 Benjamin St

2 bd · 1 ba · 1,398 sqft · 8.58 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,9272025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

129 Benjamin St

2 bd · 2 ba · 1,264 sqft · 1.35 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$280,000Mar 2021 $3,9522025 Amount on Record Jun 2015 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

135 Benjamin St

2 bd · 1 ba · 1,050 sqft · 2.06 acres

Last Sale Tax Bill Prior Sale Owner Records
$145,900Mar 2003 $3,4202025 Amount on Record May 1998 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

141 Benjamin St

2 bd · 2.5 ba · 2,376 sqft · 1.13 acres

Last Sale Tax Bill Prior Sale Owner Records
$253,000Sep 2004 $5,3392025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

147 Benjamin St

3 bd · 1 ba · 1,296 sqft · 1 acres

Last Sale Tax Bill Prior Sale Owner Records
$128,000Apr 2017 $4,5732025 Amount on Record Jan 2017 1 Name on Record Owner Occupied Assessor + 4 DocumentsUpdated Jul 2026

153 Benjamin St

2 bd · 1 ba · 864 sqft · 1 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$155,900Jun 2003 $3,3592025 Amount on Record Jan 1999 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

159 Benjamin St

3 bd · 2 ba · 1,446 sqft · 1 acres

Last Sale Tax Bill Prior Sale Owner Records
$395,000Jul 2025 $3,5632025 Amount on Record Nov 2011 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

165 Benjamin St

27 acres

Last Sale Tax Bill Prior Sale Owner Records
$149,900May 2025 $9452025 1 Name on Record Assessor + 1 DocumentUpdated Apr 2026

177 Benjamin St

2 bd · 1 ba · 1,296 sqft · 19.2 acres

Last Sale Tax Bill Prior Sale Owner Records
$16,500Sep 2008 $4,2542025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

300 Benjamin St

3 bd · 1.5 ba · 1,232 sqft · 0.85 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$98,000Jan 2001 $3,3162025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

305 Benjamin St

3 bd · 2.5 ba · 2,667 sqft · 0.7 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$485,000Jun 2026 $4,2642025 —Jan 2016 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

306 Benjamin St

3 bd · 2 ba · 1,460 sqft · 1.21 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$144,900Mar 2013 $4,2582025 Amount on Record May 2012 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

313 Benjamin St

4 bd · 2.5 ba · 2,320 sqft · 2.5 acres

Last Sale Tax Bill Prior Sale Owner Records
$175,000Jul 2008 $4,5772025 Amount on Record Apr 2008 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

314 Benjamin St

3 bd · 2 ba · 1,628 sqft · 0.703 acres

Last Sale Tax Bill Prior Sale Owner Records
$185,000Oct 2016 $3,8192025 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

320 Benjamin St

2 bd · 1.5 ba · 1,718 sqft · 2.5 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$240,000Apr 2014 $5,4292025 Amount on Record Oct 2011 1 Name on Record Owner Occupied AssessorUpdated Apr 2026

330 Benjamin St

2 bd · 4 ba · 2,070 sqft · 3.13 acres

Last Sale Tax Bill Prior Sale Owner Records
$525,000Jun 2026 $5,5992025 Amount on Record Apr 2014 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

333 Benjamin St

3 bd · 1.5 ba · 1,630 sqft · 1 acres

Last Sale Tax Bill Prior Sale Owner Records
$155,900May 2012 $4,5882025 Amount on Record — 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

334 Benjamin St

2.5 ba · 1,396 sqft · 1.19 acres

Last Sale Tax Bill Prior Sale Owner Records
$325,000Jul 2021 $4,1152025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

340 Benjamin St

2.5 ba · 1,396 sqft · 1.25 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$311,550Mar 2021 $4,2792025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

350 Benjamin St

3 bd · 2.5 ba · 3,041 sqft · 1.76 acres

Last Sale Tax Bill Prior Sale Owner Records
$445,000Oct 2022 $5,9812025 Amount on Record Dec 2020 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

353 Benjamin St

4 bd · 2.5 ba · 3,561 sqft · 6.5 acres

Last Sale Tax Bill Prior Sale Owner Records
$253,000Sep 2013 $4,2522025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

361 Benjamin St

2 bd · 1 ba · 1,422 sqft · 2 acres

Last Sale Tax Bill Prior Sale Owner Records
$249,000Sep 2021 $3,4512025 Amount on Record Mar 2013 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

364 Benjamin St

4 bd · 2.5 ba · 2,100 sqft · 4.33 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$215,000Mar 2011 $3,6722025 —Mar 2008 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

365 Benjamin St

5 bd · 2.5 ba · 2,464 sqft · 5.49 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$324,730Feb 2017 $6,5072025 Amount on Record Aug 2003 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

Wildfire Risk on Benjamin St

Source: USDA Forest Service Wildfire Risk to Communities · 2nd edition (2024), fuels as of 2020

Wildfire RiskLow
this street's cells rank at the 20th percentile of exposed land nationally · 58th in Massachusetts
Wildfire LikelihoodLow — about 1 in 10,000 per year
ExposureDirect
9 of 10 cells directly exposed · 10 adjoin burnable vegetation

Property Records in Nearby Streets