Windsor Ave, Pittsfield, MA Property Records

Berkshire County and Pittsfield City property records for 49 addresses on Windsor Ave, Pittsfield, MA · Last verified August 2026

Windsor Ave Highlights

Properties 49
Median Sale Price $290,000
Deeds and Mortgages on File 47
Median Price per Sqft $208
Owner Occupied 94%
Median Annual Tax Bill $5,027
Median Year Built 1947
Median Ownership Tenure 17 years

Properties on Windsor Ave

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

14 Windsor Ave

4 bd · 1 ba · 1,622 sqft · 0.228 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$155,000Dec 1994 $5,1002025 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

20 Windsor Ave

3 bd · 2 ba · 1,930 sqft · 0.228 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$186,500Aug 2018 $5,5582025 Amount on Record Nov 2004 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

21 Windsor Ave

3 bd · 1.5 ba · 1,427 sqft · 0.249 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$39,500Sep 1980 $5,4882025 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

25 Windsor Ave

4 bd · 1.5 ba · 1,392 sqft · 0.265 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$215,000Oct 2020 $5,0682025 Amount on Record Jan 2005 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

26 Windsor Ave

2 bd · 1 ba · 1,062 sqft · 0.341 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$92,500Jan 2001 $4,1332025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

31 Windsor Ave

4 bd · 1 ba · 2,288 sqft · 0.515 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$6,6112025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

36 Windsor Ave

4 bd · 1 ba · 1,709 sqft · 0.343 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$5,9562025 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

39 Windsor Ave

3 bd · 1.5 ba · 1,350 sqft · 0.257 acres

Last Sale Tax Bill Prior Sale Owner Records
$92,500Dec 1998 $5,0272025 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

42 Windsor Ave

3 bd · 1 ba · 1,633 sqft · 0.228 acres

Last Sale Tax Bill Prior Sale Owner Records
$5,3262025 1 Name on Record Owner Occupied AssessorUpdated Apr 2026

46 Windsor Ave

3 bd · 1 ba · 1,395 sqft · 0.208 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$152,500Mar 2006 $4,8422025 Amount on Record Apr 2005 1 Name on Record Owner Occupied AssessorUpdated Apr 2026

47 Windsor Ave

3 bd · 1.5 ba · 1,698 sqft · 0.327 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$238,500Nov 2019 $5,6922025 Amount on Record Aug 2004 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

48 Windsor Ave

3 bd · 1.5 ba · 1,540 sqft · 0.207 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$33,500Oct 1977 $5,3682025 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

54 Windsor Ave

3 bd · 1.5 ba · 1,560 sqft · 0.225 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$50,000Oct 2001 $5,3212025 1 Name on Record Owner Occupied AssessorUpdated Apr 2026

55 Windsor Ave

3 bd · 2 ba · 2,040 sqft · 0.296 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$6,3622025 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

71 Windsor Ave

3 bd · 1 ba · 1,641 sqft · 0.185 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$125,900Aug 2001 $4,2772025 Amount on Record Aug 2000 1 Name on Record Owner Occupied Assessor + 5 DocumentsUpdated Apr 2026

74 Windsor Ave

3 bd · 1.5 ba · 1,188 sqft · 0.225 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$221,000Nov 2020 $4,7042025 Amount on Record Sep 2000 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

77 Windsor Ave

3 bd · 2 ba · 1,168 sqft · 0.26 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$292,000Aug 2024 $4,6882025 Amount on Record Sep 2006 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

80 Windsor Ave

3 bd · 1 ba · 1,512 sqft · 0.257 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$84,000Aug 2002 $5,2732025 1 Name on Record Owner Occupied AssessorUpdated Apr 2026

81 Windsor Ave

3 bd · 1.5 ba · 1,546 sqft · 0.26 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$96,000Aug 1995 $5,3712025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

84 Windsor Ave

3 bd · 1.5 ba · 1,782 sqft · 0.257 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$197,000Sep 2017 $6,0602025 Amount on Record Dec 2010 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

87 Windsor Ave

3 bd · 1 ba · 1,336 sqft · 0.26 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$4,9462025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

88 Windsor Ave

3 bd · 1 ba · 1,350 sqft · 0.257 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$19,000Aug 1983 $5,1542025 1 Name on Record Owner Occupied AssessorUpdated Apr 2026

92 Windsor Ave

3 bd · 1 ba · 1,350 sqft · 0.257 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$115,000Aug 1997 $4,9392025 Amount on Record Feb 1987 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

93 Windsor Ave

3 bd · 1 ba · 1,478 sqft · 0.26 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$230,500Jan 2024 $4,4712025 Amount on Record Jan 2010 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

96 Windsor Ave

2 bd · 1 ba · 1,353 sqft · 0.257 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$138,000Feb 2005 $5,1252025 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

99 Windsor Ave

3 bd · 1.5 ba · 1,305 sqft · 0.26 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$145,000Aug 2005 $4,9802025 1 Name on Record AssessorUpdated Apr 2026

101 Windsor Ave

3 bd · 1 ba · 1,103 sqft · 0.26 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$4,8872025 1 Name on Record Owner Occupied AssessorUpdated Apr 2026

102 Windsor Ave

3 bd · 1 ba · 1,267 sqft · 0.351 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$290,000Apr 2024 $4,7742025 Amount on Record Mar 2001 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

106 Windsor Ave

2 bd · 2 ba · 1,353 sqft · 0.29 acres

Last Sale Tax Bill Prior Sale Owner Records
$179,000Nov 2019 $4,4622025 Amount on Record Aug 2002 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

111 Windsor Ave

3 bd · 2 ba · 1,404 sqft · 0.35 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$128,000Oct 2001 $5,8502025 Amount on Record Jul 1996 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

112 Windsor Ave

3 bd · 1 ba · 1,152 sqft · 0.232 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$173,750Jul 2008 $4,5012025 Amount on Record Oct 2004 1 Name on Record Owner Occupied AssessorUpdated Apr 2026

118 Windsor Ave

3 bd · 1 ba · 976 sqft · 0.227 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$106,500Jan 2016 $3,7622025 Amount on Record Jan 2012 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

121 Windsor Ave

3 bd · 1 ba · 1,613 sqft · 0.278 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$124,900May 2001 $4,5412025 1 Name on Record Owner Occupied AssessorUpdated Apr 2026

124 Windsor Ave

3 bd · 2 ba · 1,644 sqft · 0.216 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$195,400Nov 2018 $5,7232025 Amount on Record Oct 2018 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

130 Windsor Ave

3 bd · 1 ba · 1,473 sqft · 0.266 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$127,500Jun 2003 $5,2032025 1 Name on Record Owner Occupied AssessorUpdated Apr 2026

136 Windsor Ave

2 bd · 1 ba · 1,144 sqft · 0.28 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
—Aug 2017 $4,5692025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

140 Windsor Ave

3 bd · 1 ba · 1,353 sqft · 0.245 acres

Last Sale Tax Bill Prior Sale Owner Records
$118,000Sep 2015 $3,8412025 Amount on Record Jun 2012 1 Name on Record Owner Occupied AssessorUpdated Apr 2026

144 Windsor Ave

2 bd · 1 ba · 970 sqft · 0.206 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$133,000Oct 2009 $3,6422025 Amount on Record Mar 2009 1 Name on Record Owner Occupied AssessorUpdated Apr 2026

150 Windsor Ave

2.3 acres

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

154 Windsor Ave

3 bd · 2 ba · 1,689 sqft · 0.241 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$5,4902025 1 Name on Record Owner Occupied AssessorUpdated Apr 2026

158 Windsor Ave

2 bd · 2 ba · 940 sqft · 0.241 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$179,400Nov 2019 $4,3852025 2 Names on Record Assessor + 3 DocumentsUpdated Aug 2026

164 Windsor Ave

3 bd · 1 ba · 1,288 sqft · 0.241 acres

Last Sale Tax Bill Prior Sale Owner Records
$4,3582025 1 Name on Record Owner Occupied AssessorUpdated Apr 2026

170 Windsor Ave

2 bd · 1 ba · 1,072 sqft · 0.241 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$156,000Apr 2009 $4,8332025 Amount on Record Dec 2003 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

176 Windsor Ave

3 bd · 1 ba · 1,353 sqft · 0.251 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$339,900Jul 2025 $4,8742025 Amount on Record Dec 2021 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

188 Windsor Ave

3 bd · 2 ba · 2,036 sqft · 0.227 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$425,000Feb 2025 $6,4102025 Amount on Record Jun 2023 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

194 Windsor Ave

3 bd · 1.5 ba · 1,248 sqft · 0.227 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$136,000Nov 2018 $3,9592025 Amount on Record Jul 2003 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Apr 2026

198 Windsor Ave

3 bd · 1 ba · 1,545 sqft · 0.227 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$34,000Nov 1981 $4,3882025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

201 Windsor Ave

3 bd · 1.5 ba · 1,804 sqft · 0.237 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$239,900Nov 2019 $5,4862025 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

206 Windsor Ave

4 bd · 2.5 ba · 1,858 sqft · 0.454 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$175,000Feb 2015 $6,6902025 Amount on Record Oct 1987 1 Name on Record Owner Occupied AssessorUpdated Apr 2026

Wildfire Risk on Windsor Ave

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

Wildfire Risk to HomesLow
this street's cells rank at the 20th percentile of exposed land nationally · 58th in Massachusetts
Wildfire LikelihoodLow — less than 1 in 10,000 per year
ExposureDirect
3 of 6 cells directly exposed · 5 adjoin burnable vegetation

Property Records in Nearby Streets