Main St, Winchendon, MA Property Records

Worcester County and Winchendon Town property records for 69 addresses on Main St, Winchendon, MA · Last verified August 2026

Main St Highlights

Properties 69
Median Sale Price $349,900
Deeds and Mortgages on File 74
Median Price per Sqft $219
Owner Occupied 62%
Median Annual Tax Bill $3,145
Median Year Built 1939
Median Ownership Tenure 13 years

Properties on Main St

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

11 Main St

10 bd · 6 ba · 5,199 sqft · built 1876 · 0.269 acres

Last Sale Tax Bill Prior Sale Owner Records
$769,500Dec 2024 $4,9082025 Amount on Record Apr 2023 2 Owners on Record Assessor + 7 DocumentsUpdated Apr 2026

16 Main St

4 ba · 10,200 sqft · built 1986 · 3.23 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,000,000Jun 2023 $7,8852025 Owner on Record Assessor + 1 DocumentUpdated Apr 2026

25 Main St

3 bd · 1.5 ba · 2,785 sqft · built 1845 · 0.78 acres

Last Sale Tax Bill Prior Sale Owner Records
$22,000Jul 2014 $7762025 2 Owners on Record Assessor + 1 DocumentUpdated Aug 2026

56 Main St

2 bd · 1 ba · 1,302 sqft · built 1870 · 0.589 acres

Last Sale Tax Bill Prior Sale Owner Records
$30,000Aug 2012 $2,6672025 Amount on Record Nov 2011 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

64 Main St

4 bd · 2 ba · 1,750 sqft · built 1932 · 0.669 acres

Last Sale Tax Bill Prior Sale Owner Records
—Jul 2015 $2,5942025 2 Owners on Record Owner Occupied AssessorUpdated Jul 2026

69 Main St

4 bd · 2 ba · 1,464 sqft · built 1870 · 0.63 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,6652025 Owner on Record AssessorUpdated Apr 2026

75 Main St

3 bd · 1.5 ba · 1,458 sqft · built 1870 · 0.375 acres

Last Sale Tax Bill Prior Sale Owner Records
$76,100Oct 1991 $2,4122025 Amount on Record Mar 1987 2 Owners on Record Owner Occupied AssessorUpdated Jul 2026

76 Main St

3 bd · 2 ba · 1,733 sqft · built 1870 · 0.75 acres

Last Sale Tax Bill Prior Sale Owner Records
$223,000Jul 2019 $3,9632025 Amount on Record Dec 2017 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

81 Main St

3 bd · 1 ba · 1,449 sqft · built 1878 · 0.38 acres

Last Sale Tax Bill Prior Sale Owner Records
$86,000Jan 2008 $2,6212025 Amount on Record Jan 2000 Owner on Record Owner Occupied AssessorUpdated Jul 2026

86 Main St

3 bd · 1 ba · 1,122 sqft · built 1870 · 0.319 acres

Last Sale Tax Bill Prior Sale Owner Records
—Apr 2010 $1,6462025 Owner on Record Owner Occupied AssessorUpdated Jul 2026

94 Main St

3 bd · 1.5 ba · 1,334 sqft · built 1900 · 0.23 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,3502025 2 Owners on Record Owner Occupied AssessorUpdated Jul 2026

103 Main St

3 bd · 2.5 ba · 1,946 sqft · built 1870 · 0.46 acres

Last Sale Tax Bill Prior Sale Owner Records
$105,000Oct 1987 $3,1452025 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

109 Main St

2 bd · 1 ba · 855 sqft · built 1841 · 0.46 acres

Last Sale Tax Bill Prior Sale Owner Records
$62,000Mar 1995 $3,1472025 2 Owners on Record Owner Occupied AssessorUpdated Jul 2026

120 Main St

5 bd · 2 ba · 2,233 sqft · built 1920 · 0.61 acres

Last Sale Tax Bill Prior Sale Owner Records
$92,000Jun 1997 $2,6262025 2 Owners on Record Owner Occupied AssessorUpdated Apr 2026

121 Main St

3 bd · 1.5 ba · 1,246 sqft · built 1910 · 2 acres

Last Sale Tax Bill Prior Sale Owner Records
$165,000Jul 2015 $4,1642025 Amount on Record Oct 2014 2 Owners on Record Owner Occupied AssessorUpdated Jul 2026

140 Main St

3 bd · 2 ba · 1,257 sqft · built 1891 · 0.439 acres

Last Sale Tax Bill Prior Sale Owner Records
$276,000Apr 2021 $3,5572025 Amount on Record May 2019 Owner on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

141 Main St

3 bd · 1.5 ba · 1,559 sqft · built 1870 · 0.93 acres

Last Sale Tax Bill Prior Sale Owner Records
$925,000Jul 1987 $3,1172025 2 Owners on Record Owner Occupied AssessorUpdated Jul 2026

146 Main St

0.98 acres

Last Sale Tax Bill Prior Sale Owner Records
$260,000Apr 2021 $3,1362025 Amount on Record May 2003 Owner on Record Assessor + 1 DocumentUpdated Jul 2026

162 Main St

2 bd · 1 ba · 752 sqft · built 1900 · 2.28 acres

Last Sale Tax Bill Prior Sale Owner Records
$20,000Mar 2013 $1,6072025 Owner on Record Owner Occupied Assessor + 4 DocumentsUpdated Jul 2026

169 Main St

3 bd · 1 ba · 1,330 sqft · built 1836 · 0.725 acres

Last Sale Tax Bill Prior Sale Owner Records
$40,500Mar 2016 $2,5252025 Amount on Record Jan 2016 2 Owners on Record AssessorUpdated Jul 2026

175 Main St

5 bd · 1.5 ba · 1,701 sqft · built 1870 · 6.38 acres

Last Sale Tax Bill Prior Sale Owner Records
$33,000Mar 1983 $4,3962025 2 Owners on Record AssessorUpdated Jul 2026

192 Main St

1 bd · 1 ba · 720 sqft · built 1900 · 1 acres

Last Sale Tax Bill Prior Sale Owner Records
$87,500Aug 2019 $2,3952025 Amount on Record Oct 2014 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

195 Main St

3 bd · 1.5 ba · 1,815 sqft · built 1870 · 0.539 acres

Last Sale Tax Bill Prior Sale Owner Records
$217,000May 2006 $3,2272025 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

209 Main St

0.66 acres

Last Sale Tax Bill Prior Sale Owner Records
—Nov 2012 $3,5202025 —Nov 2012 Owner on Record Assessor + 2 DocumentsUpdated Aug 2026

213 Main St

3 bd · 1 ba · 1,165 sqft · built 1900 · 0.63 acres

Last Sale Tax Bill Prior Sale Owner Records
$78,650Feb 2013 $2,5182025 Owner on Record Owner Occupied AssessorUpdated Jul 2026

214 Main St

5 bd · 1.5 ba · 1,900 sqft · built 1821 · 0.675 acres

Last Sale Tax Bill Prior Sale Owner Records
$105,000Jan 2012 $3,0862025 Amount on Record Oct 2006 2 Owners on Record Owner Occupied AssessorUpdated Jul 2026

222 Main St

198 sqft · built 1994 · 2.04 acres

Last Sale Tax Bill Prior Sale Owner Records
$70,000Oct 2025 $7632025 Owner on Record Assessor + 2 DocumentsUpdated Jul 2026

231 Main St

1 ba · 1,152 sqft · built 1961 · 0.991 acres

Last Sale Tax Bill Prior Sale Owner Records
$256,700Sep 2023 $1,9192025 Amount on Record Apr 2015 Owner on Record Assessor + 2 DocumentsUpdated Apr 2026

233 Main St

5 bd · 2.5 ba · 2,844 sqft · built 1900 · 5.25 acres

Last Sale Tax Bill Prior Sale Owner Records
$350,000Aug 2024 $3,4242025 Amount on Record Dec 1981 Owner on Record Assessor + 2 DocumentsUpdated Apr 2026

237 Main St

1 ba · 2,024 sqft · built 1924 · 0.2 acres

Last Sale Tax Bill Prior Sale Owner Records
$4,200Feb 2013 $1,3972025 2 Owners on Record AssessorUpdated Apr 2026

239 Main St

7 bd · 4 ba · 5,220 sqft · built 1940 · 1 acres

Last Sale Tax Bill Prior Sale Owner Records
$195,670Jun 2012 $3,4432025 Amount on Record Jul 2004 Owner on Record AssessorUpdated Aug 2026

240 Main St

2 bd · 1 ba · 1,752 sqft · built 1977 · 15 acres

Last Sale Tax Bill Prior Sale Owner Records
$80,000Oct 2006 $4,8412025 2 Owners on Record Assessor + 1 DocumentUpdated Jul 2026

242 Main St

2 bd · 1 ba · 860 sqft · built 1900 · 0.48 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,9332025 Owner on Record Owner Occupied AssessorUpdated Jul 2026

245 Main St

2 bd · 1 ba · 704 sqft · built 1939 · 0.81 acres

Last Sale Tax Bill Prior Sale Owner Records
$103,000Dec 2001 $1,7202025 Amount on Record Oct 2001 2 Owners on Record Owner Occupied AssessorUpdated Jul 2026

251 Main St

3 bd · 2 ba · 2,266 sqft · built 1976 · 2.7 acres

Last Sale Tax Bill Prior Sale Owner Records
$10,000Jun 2018 $5,5152025 Amount on Record Nov 2017 Owner on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

255 Main St

2 bd · 1 ba · 720 sqft · built 1940 · 0.319 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,6262025 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

255R Main St

3 bd · 1 ba · 1,365 sqft · built 1942 · 3.56 acres

Last Sale Tax Bill Prior Sale Owner Records
$125,000Jul 2018 $2,8562025 Amount on Record Dec 2017 2 Owners on Record Assessor + 2 DocumentsUpdated Jul 2026

256 Main St

3 bd · 1.5 ba · 1,536 sqft · built 2003 · 1.68 acres

Last Sale Tax Bill Prior Sale Owner Records
$319,000Dec 2021 $3,9802025 Amount on Record Jul 2003 Owner on Record Assessor + 2 DocumentsUpdated Jul 2026

257 Main St

2 bd · 1.5 ba · 1,246 sqft · built 1940 · 0.239 acres

Last Sale Tax Bill Prior Sale Owner Records
$250,000Jan 2022 $2,6832025 Amount on Record Feb 2020 Owner on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

259 Main St

3 bd · 1 ba · 1,116 sqft · built 1940 · 0.25 acres

Last Sale Tax Bill Prior Sale Owner Records
$128,500Apr 2015 $2,1812025 Amount on Record Jul 2014 Owner on Record AssessorUpdated Jul 2026

262 Main St

2 bd · 1 ba · 1,022 sqft · built 1935 · 0.53 acres

Last Sale Tax Bill Prior Sale Owner Records
$30,000Mar 2011 $1,7992025 Amount on Record Dec 2010 2 Owners on Record AssessorUpdated Jul 2026

265 Main St

2 bd · 1 ba · 1,046 sqft · built 1920 · 0.46 acres

Last Sale Tax Bill Prior Sale Owner Records
$25,000Mar 2018 $1,8332025 Amount on Record May 2017 Owner on Record Assessor + 2 DocumentsUpdated Jul 2026

269 Main St

4 bd · 1 ba · 1,584 sqft · built 1900 · 2.7 acres

Last Sale Tax Bill Prior Sale Owner Records
$55,000Nov 2000 $1,6492025 Owner on Record Owner Occupied AssessorUpdated Jul 2026

275 Main St

1.57 acres

Last Sale Tax Bill Prior Sale Owner Records
—Dec 2004 $5792025 2 Owners on Record AssessorUpdated Apr 2026

280 Main St

3 bd · 2 ba · 1,670 sqft · built 1963 · 1.56 acres

Last Sale Tax Bill Prior Sale Owner Records
$375,000Nov 2024 $4,0482025 Amount on Record Apr 2018 Owner on Record Owner Occupied Assessor + 4 DocumentsUpdated Jul 2026

285 Main St

3 bd · 1 ba · 2,376 sqft · built 1934 · 0.95 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,0632025 2 Owners on Record Assessor + 1 DocumentUpdated Jul 2026

286 Main St

2 bd · 1 ba · 911 sqft · built 1958 · 0.33 acres

Last Sale Tax Bill Prior Sale Owner Records
$25,000Mar 2000 $9792025 Owner on Record Owner Occupied AssessorUpdated Jul 2026

288 Main St

2 bd · 1 ba · 822 sqft · built 1959 · 0.278 acres

Last Sale Tax Bill Prior Sale Owner Records
$7,000Sep 1982 $9342025 2 Owners on Record AssessorUpdated Jul 2026

290 Main St

0.282 acres

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

294 Main St

2 bd · 1 ba · 1,155 sqft · built 1930 · 1.9 acres

Last Sale Tax Bill Prior Sale Owner Records
—Feb 2009 $2,4122025 2 Owners on Record Owner Occupied Assessor + 3 DocumentsUpdated Aug 2026

310 Main St

2 bd · 1 ba · 1,376 sqft · built 1984 · 0.8 acres

Last Sale Tax Bill Prior Sale Owner Records
$179,900Feb 2004 $3,3532025 Amount on Record Aug 2001 Owner on Record Owner Occupied AssessorUpdated Jul 2026

312 Main St

2 bd · 1 ba · 2,149 sqft · built 1984 · 0.76 acres

Last Sale Tax Bill Prior Sale Owner Records
$3,8342025 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

314 Main St

3 bd · 1.5 ba · 1,780 sqft · built 1984 · 0.73 acres

Last Sale Tax Bill Prior Sale Owner Records
$225,000Jul 2018 $4,4202025 Amount on Record Feb 2018 2 Owners on Record Owner Occupied Assessor + 4 DocumentsUpdated Jul 2026

317 Main St

3 bd · 1 ba · 1,734 sqft · built 1985 · 0.969 acres

Last Sale Tax Bill Prior Sale Owner Records
$102,000Jun 1987 $3,7742025 2 Owners on Record Owner Occupied AssessorUpdated Jul 2026

319 Main St

3 bd · 3 ba · 3,234 sqft · built 1984 · 0.93 acres

Last Sale Tax Bill Prior Sale Owner Records
$4,4332025 Owner on Record Owner Occupied AssessorUpdated Jul 2026

324 Main St

2 bd · 1 ba · 1,287 sqft · built 1922 · 2.75 acres

Last Sale Tax Bill Prior Sale Owner Records
$3,0632025 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

327 Main St

3 bd · 1.5 ba · 1,927 sqft · built 1986 · 2.05 acres

Last Sale Tax Bill Prior Sale Owner Records
—Jan 2015 $4,1222025 Amount on Record Feb 2013 2 Owners on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

337 Main St

3 bd · 2.5 ba · 1,812 sqft · built 2003 · 8.11 acres

Last Sale Tax Bill Prior Sale Owner Records
$5,1642025 2 Owners on Record Assessor + 1 DocumentUpdated Jul 2026

347 Main St

3 bd · 1.5 ba · 1,945 sqft · built 1978 · 3.01 acres

Last Sale Tax Bill Prior Sale Owner Records
$3,9392025 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

349 Main St

3 bd · 2.5 ba · 1,708 sqft · built 1981 · 3.98 acres

Last Sale Tax Bill Prior Sale Owner Records
$4,8892025 2 Owners on Record Assessor + 1 DocumentUpdated Jul 2026

350 Main St

4 bd · 2 ba · 2,349 sqft · built 1958 · 2.5 acres

Last Sale Tax Bill Prior Sale Owner Records
$4,1372025 2 Owners on Record Owner Occupied AssessorUpdated Jul 2026

354 Main St

3 bd · 2 ba · 1,560 sqft · built 1989 · 47.2 acres

Last Sale Tax Bill Prior Sale Owner Records
$4,9752025 2 Owners on Record Owner Occupied AssessorUpdated Jul 2026

357 Main St

2 bd · 1 ba · 1,344 sqft · built 1987 · 1 acres

Last Sale Tax Bill Prior Sale Owner Records
$22,500Jul 1985 $3,5492025 2 Owners on Record Owner Occupied AssessorUpdated Jul 2026

358 Main St

3 bd · 1 ba · 1,584 sqft · built 1989 · 2.02 acres

Last Sale Tax Bill Prior Sale Owner Records
$131,500Jun 2010 $3,5392025 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

359 Main St

3 bd · 2 ba · 1,900 sqft · built 1996 · 8.93 acres

Last Sale Tax Bill Prior Sale Owner Records
$282,450Jun 2007 $5,9292025 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

361 Main St

3 bd · 1.5 ba · 1,381 sqft · built 1984 · 2.8 acres

Last Sale Tax Bill Prior Sale Owner Records
$349,900Oct 2022 $4,2482025 Amount on Record Dec 1983 Owner on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

362 Main St

2 bd · 1 ba · 1,092 sqft · built 1990 · 2 acres

Last Sale Tax Bill Prior Sale Owner Records
$3,5382025 2 Owners on Record AssessorUpdated Jul 2026

365 Main St

3 bd · 1.5 ba · 1,244 sqft · built 1983 · 3.93 acres

Last Sale Tax Bill Prior Sale Owner Records
$450,000Nov 2023 $5,4142025 Amount on Record Jun 2019 2 Owners on Record Owner Occupied Assessor + 5 DocumentsUpdated Jul 2026

366 Main St

2 bd · 1 ba · 898 sqft · built 1997 · 2.01 acres

Last Sale Tax Bill Prior Sale Owner Records
$80,200Dec 1997 $3,5452025 Owner on Record Owner Occupied AssessorUpdated Jul 2026

Property Records in Nearby Streets