Winter St, Pittsfield, MA Property Records

Berkshire County and Pittsfield City property records for 22 addresses on Winter St, Pittsfield, MA · Last verified July 2026

Winter St Highlights

Properties 22
Median Sale Price $102,500
Deeds and Mortgages on File 18
Median Price per Sqft $62
Owner Occupied 68%
Median Annual Tax Bill $3,148
Median Year Built 1900
Median Ownership Tenure 15 years

Properties on Winter St

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

7 Winter St

7,000 sqft · Built 1917 · 0.478 acres

Last Sale Tax Bill Prior Sale Owner Records
$158,000Feb 2013 $11,9762025 Sale Amount Mar 2005 2 Names on Record Assessor + 1 DocumentUpdated Apr 2026

10 Winter St

8 bd · 4 ba · 3,528 sqft · 0.105 acres

Last Sale Tax Bill Prior Sale Owner Records
$60,500Nov 2018 $5202025 —Jan 2015 1 Name on Record Assessor + 1 DocumentUpdated Apr 2026

14 Winter St

5 bd · 2 ba · 2,638 sqft · 0.212 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$100,000Dec 1987 $4,1352025 1 Name on Record AssessorUpdated Apr 2026

20 Winter St

4 bd · 1 ba · 1,185 sqft · 0.212 acres

Last Sale Tax Bill Prior Sale Owner Records
$10,000Sep 1990 $3,6182025 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

25 Winter St

0.938 acres

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

26 Winter St

7 bd · 2 ba · 3,306 sqft · 0.212 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
—Sep 2010 $4,7902025 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

34 Winter St

3 bd · 2 ba · 1,648 sqft · 0.212 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$102,500Dec 2019 $3,1482025 Sale Amount Feb 1990 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

37 Winter St

2 bd · 1.5 ba · 1,662 sqft · 0.218 acres

Last Sale Tax Bill Prior Sale Owner Records
$50,000Mar 2000 $3,5342025 Sale Amount Jun 1995 1 Name on Record Owner Occupied AssessorUpdated Apr 2026

38 Winter St

2 bd · 1.5 ba · 1,546 sqft · 0.153 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$58,100Jun 2021 $2,2642025 Sale Amount Apr 2021 2 Names on Record Assessor + 4 DocumentsUpdated Apr 2026

41 Winter St

3 bd · 1 ba · 1,641 sqft · 0.181 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$115,000Apr 2016 $3,5002025 Sale Amount Jun 2015 1 Name on Record Owner Occupied AssessorUpdated Apr 2026

42 Winter St

3 bd · 1 ba · 1,218 sqft · 0.169 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$38,000Sep 1994 $3,2472025 1 Name on Record Owner Occupied AssessorUpdated Apr 2026

45 Winter St

3 bd · 2.5 ba · 1,943 sqft · 0.181 acres

Last Sale Tax Bill Prior Sale Owner Records
$55,000Jul 2002 $2,3562025 1 Name on Record Owner Occupied AssessorUpdated Apr 2026

46 Winter St

4 bd · 1.5 ba · 1,152 sqft · 0.169 acres

Last Sale Tax Bill Prior Sale Owner Records
$89,900Oct 2014 $2,6862025 Sale Amount Aug 2004 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

48 Winter St

3 bd · 1 ba · 1,584 sqft · 0.095 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$73,000May 2017 $2,2962025 Sale Amount May 1994 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

49 Winter St

3 bd · 1 ba · 1,760 sqft · 0.16 acres

Last Sale Tax Bill Prior Sale Owner Records
$50,000Sep 1992 $3,2422025 Sale Amount Sep 1991 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

50 Winter St

2 bd · 1.5 ba · 1,121 sqft · 0.079 acres

Last Sale Tax Bill Prior Sale Owner Records
$18,000Mar 1993 $2,6612025 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

53 Winter St

3 bd · 1.5 ba · 1,344 sqft · 0.181 acres

Last Sale Tax Bill Prior Sale Owner Records
$231,150May 2025 $3,8122025 Sale Amount Oct 2020 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated Apr 2026

54 Winter St

3 bd · 1.5 ba · 1,488 sqft · 0.16 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$116,000Oct 2009 $3,9842025 Sale Amount Feb 2009 1 Name on Record Owner Occupied AssessorUpdated Apr 2026

57 Winter St

3 bd · 1 ba · 1,320 sqft · 0.075 acres

Last Sale Tax Bill Prior Sale Owner Records
$92,700Apr 2019 $2,7112025 Sale Amount Apr 2015 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

58 1/2 Winter St

2 bd · 1 ba · 923 sqft · 0.063 acres

Last Sale Tax Bill Prior Sale Owner Records
$42,000Jun 2011 $1,8162025 1 Name on Record Assessor + 1 DocumentUpdated Apr 2026

58 Winter St

4 bd · 1.5 ba · 1,592 sqft · 0.078 acres

Last Sale Tax Bill Prior Sale Owner Records
$44,500Nov 2010 $2,2892025 Sale Amount Apr 1990 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

60 Winter St

6 bd · 2 ba · 3,200 sqft · 0.196 acres

Last Sale Tax Bill Prior Sale Owner Records
$145,000Jun 2022 $2,9782025 Sale Amount Aug 2006 1 Name on Record Assessor + 1 DocumentUpdated Apr 2026

Property Records in Nearby Streets