Berkshire County and Pittsfield City property records for 51 addresses on Winesap Rd, Pittsfield, MA · Last verified October 2026
| Properties | 51 |
|---|---|
| Median Sale Price | $386,600 |
| Deeds and Mortgages on File | 48 |
| Median Price per Sqft | $211 |
| Owner Occupied | 96% |
| Median Annual Tax Bill | $6,815 |
| Median Year Built | 1982 |
| Median Ownership Tenure | 16 years |
Owner names and prior sale amounts shown locked below are available instantly with a free trial.
3 bd · 1 ba · 1,494 sqft · built 1979 · 0.277 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $39,000Nov 1979 | $5,5852025 | 2 Owners on Record Owner Occupied | AssessorUpdated Jul 2026 |
3 bd · 2 ba · 1,934 sqft · built 1980 · 0.329 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $132,000Oct 1992 | $6,6702025 | 2 Owners on Record | Assessor + 2 DocumentsUpdated Apr 2026 |
3 bd · 2 ba · 1,494 sqft · built 1978 · 0.282 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $6,1102025 | 2 Owners on Record Owner Occupied | AssessorUpdated Jul 2026 |
3 bd · 2 ba · 1,494 sqft · built 1980 · 0.328 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $360,000Nov 2023 | $5,9362025 | Amount on Record Aug 2018 | Owner on Record Owner Occupied | Assessor + 3 DocumentsUpdated Oct 2026 |
3 bd · 2 ba · 1,368 sqft · built 1979 · 0.31 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $427,000Mar 2025 | $6,2492025 | Amount on Record Nov 2018 | 2 Owners on Record Owner Occupied | Assessor + 3 DocumentsUpdated Oct 2026 |
2 bd · 2 ba · 2,037 sqft · built 1980 · 0.329 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $146,900Aug 2000 | $7,6122025 | 2 Owners on Record Owner Occupied | AssessorUpdated Apr 2026 |
4 bd · 3 ba · 1,973 sqft · built 1980 · 0.334 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $244,000Feb 2007 | $7,5462025 | Amount on Record Nov 2003 | 2 Owners on Record Owner Occupied | Assessor + 3 DocumentsUpdated Apr 2026 |
3 bd · 2.5 ba · 1,610 sqft · built 1979 · 0.319 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $177,125Dec 2012 | $5,7232025 | Amount on Record Oct 1989 | 2 Owners on Record Owner Occupied | Assessor + 1 DocumentUpdated Apr 2026 |
4 bd · 2 ba · 1,468 sqft · built 1979 · 0.319 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $311,000Nov 2022 | $5,5942025 | Amount on Record Sep 1983 | Owner on Record Owner Occupied | Assessor + 1 DocumentUpdated Oct 2026 |
3 bd · 1.5 ba · 1,473 sqft · built 1982 · 0.326 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $127,500Oct 1999 | $6,0302025 | 2 Owners on Record Owner Occupied | AssessorUpdated Apr 2026 |
4 bd · 2 ba · 2,208 sqft · built 1983 · 0.319 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $262,000Oct 2013 | $7,0972025 | 2 Owners on Record Owner Occupied | AssessorUpdated Apr 2026 |
4 bd · 2 ba · 2,044 sqft · built 1983 · 0.319 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $180,000Aug 2004 | $6,5452025 | Amount on Record Jun 1999 | Owner on Record Owner Occupied | Assessor + 1 DocumentUpdated Apr 2026 |
3 bd · 2.5 ba · 1,720 sqft · built 1982 · 0.331 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $279,000Oct 2021 | $5,9582025 | Amount on Record Sep 2016 | Owner on Record Owner Occupied | Assessor + 1 DocumentUpdated Apr 2026 |
3 bd · 2 ba · 1,364 sqft · built 1979 · 0.332 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $115,000Aug 1993 | $5,7052025 | 2 Owners on Record Owner Occupied | AssessorUpdated Apr 2026 |
3 bd · 1.5 ba · 1,340 sqft · built 1979 · 0.319 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $30,000Oct 1989 | $6,0282025 | 2 Owners on Record Owner Occupied | AssessorUpdated Apr 2026 |
3 bd · 2 ba · 1,634 sqft · built 1980 · 0.333 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $268,000Dec 2019 | $6,2182025 | Amount on Record Jun 2015 | 2 Owners on Record Owner Occupied | Assessor + 2 DocumentsUpdated Apr 2026 |
3 bd · 1.5 ba · 1,514 sqft · built 1980 · 0.333 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $138,500Nov 1999 | $5,9632025 | Amount on Record Jun 1998 | 2 Owners on Record Owner Occupied | AssessorUpdated Apr 2026 |
3 bd · 2 ba · 1,494 sqft · built 1980 · 0.333 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $151,000Aug 2001 | $6,2742025 | Amount on Record Aug 1993 | Owner on Record Owner Occupied | Assessor + 2 DocumentsUpdated Apr 2026 |
3 bd · 2 ba · 1,672 sqft · built 1980 · 0.333 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $187,250Apr 2015 | $5,3572025 | Amount on Record Sep 1989 | 2 Owners on Record Owner Occupied | Assessor + 2 DocumentsUpdated Apr 2026 |
3 bd · 2 ba · 1,784 sqft · built 1984 · 0.334 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $205,000Feb 2016 | $6,0582025 | Amount on Record Aug 1998 | 2 Owners on Record Owner Occupied | AssessorUpdated Apr 2026 |
3 bd · 3.5 ba · 2,286 sqft · built 1980 · 0.333 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $300,000Aug 2014 | $8,6272025 | Amount on Record Sep 1993 | 2 Owners on Record Owner Occupied | Assessor + 2 DocumentsUpdated Apr 2026 |
3 bd · 2 ba · 1,444 sqft · built 1979 · 0.335 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $159,000Jul 1987 | $6,3632025 | 2 Owners on Record Owner Occupied | Assessor + 1 DocumentUpdated Apr 2026 |
3 bd · 2.5 ba · 1,736 sqft · built 1980 · 0.333 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| —Feb 2016 | $6,1392025 | Amount on Record Mar 1998 | 2 Owners on Record Owner Occupied | AssessorUpdated Apr 2026 |
3 bd · 2 ba · 2,200 sqft · built 1983 · 0.336 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $386,600Oct 2023 | $6,6652025 | Amount on Record Nov 1993 | 2 Owners on Record Owner Occupied | Assessor + 1 DocumentUpdated Apr 2026 |
4 bd · 2.5 ba · 2,224 sqft · built 1979 · 0.337 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $289,900Nov 2019 | $6,9162025 | Amount on Record Jun 2001 | Owner on Record Owner Occupied | Assessor + 4 DocumentsUpdated May 2026 |
3 bd · 2 ba · 1,505 sqft · built 1980 · 0.333 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $156,900Oct 2001 | $6,3132025 | Amount on Record Mar 1995 | 2 Owners on Record Owner Occupied | Assessor + 1 DocumentUpdated Apr 2026 |
4 bd · 2 ba · 1,934 sqft · built 1980 · 0.333 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $238,000Jun 2015 | $6,8152025 | Amount on Record Dec 2010 | Owner on Record Owner Occupied | AssessorUpdated Apr 2026 |
3 bd · 2.5 ba · 1,865 sqft · built 1979 · 0.337 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $174,000Aug 1989 | $7,0652025 | Amount on Record Jul 1987 | 2 Owners on Record | AssessorUpdated Apr 2026 |
3 bd · 2 ba · 1,714 sqft · built 1980 · 0.333 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $62,500Oct 1986 | $6,7352025 | Owner on Record Owner Occupied | AssessorUpdated Apr 2026 |
3 bd · 2 ba · 1,530 sqft · built 1979 · 0.338 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $365,000Jul 2025 | $6,2902025 | 2 Owners on Record Owner Occupied | Assessor + 1 DocumentUpdated Apr 2026 |
4 bd · 2.5 ba · 1,792 sqft · built 1985 · 0.315 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $172,500Jan 1989 | $7,4432025 | 2 Owners on Record Owner Occupied | AssessorUpdated Apr 2026 |
1 bd · 2.5 ba · 2,299 sqft · built 1985 · 0.339 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $415,000Mar 2026 | $6,0982025 | Amount on Record May 2014 | Owner on Record Owner Occupied | Assessor + 1 DocumentUpdated Apr 2026 |
4 bd · 2.5 ba · 2,112 sqft · built 1984 · 0.331 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $259,000Jul 2009 | $7,7382025 | Amount on Record Aug 2006 | 2 Owners on Record Owner Occupied | Assessor + 1 DocumentUpdated Apr 2026 |
4 bd · 3 ba · 2,676 sqft · built 1984 · 0.339 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $423,000Feb 2023 | $8,2082025 | Amount on Record Jan 2011 | Owner on Record Owner Occupied | Assessor + 4 DocumentsUpdated Oct 2026 |
3 bd · 2.5 ba · 1,802 sqft · built 1984 · 0.351 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $266,000Sep 2019 | $6,3182025 | Amount on Record Feb 1997 | 2 Owners on Record Owner Occupied | Assessor + 1 DocumentUpdated Apr 2026 |
3 bd · 2.5 ba · 2,106 sqft · built 1985 · 0.34 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $197,500Aug 2001 | $7,2462025 | Owner on Record Owner Occupied | Assessor + 3 DocumentsUpdated Jun 2026 |
3 bd · 3 ba · 2,128 sqft · built 1985 · 0.288 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $125,000Aug 1985 | $8,4262025 | 2 Owners on Record Owner Occupied | AssessorUpdated Apr 2026 |
4 bd · 2.5 ba · 2,180 sqft · built 1985 · 0.341 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $298,000Jun 2010 | $8,4892025 | 2 Owners on Record Owner Occupied | Assessor + 1 DocumentUpdated Apr 2026 |
4 bd · 2.5 ba · 2,288 sqft · built 1985 · 0.285 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| —Jun 2016 | $8,2832025 | Amount on Record Jul 1999 | Owner on Record Owner Occupied | AssessorUpdated Apr 2026 |
4 bd · 2.5 ba · 2,144 sqft · built 1985 · 0.342 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $319,000Aug 2012 | $8,0082025 | Amount on Record Mar 2011 | 2 Owners on Record Owner Occupied | Assessor + 1 DocumentUpdated Apr 2026 |
4 bd · 2.5 ba · 1,998 sqft · built 1985 · 0.3 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $257,900Jan 2013 | $8,7692025 | 2 Owners on Record Owner Occupied | AssessorUpdated Apr 2026 |
4 bd · 2.5 ba · 2,240 sqft · built 1985 · 0.343 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $160,300Nov 1998 | $7,9782025 | Amount on Record Nov 1993 | Owner on Record Owner Occupied | AssessorUpdated Apr 2026 |
4 bd · 2.5 ba · 2,128 sqft · built 1984 · 0.335 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $297,000Jun 2008 | $8,2992025 | Amount on Record Mar 2007 | Owner on Record Owner Occupied | Assessor + 1 DocumentUpdated Apr 2026 |
4 bd · 2.5 ba · 2,176 sqft · built 1984 · 0.327 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $342,000Sep 2019 | $7,9442025 | Amount on Record Aug 2001 | 2 Owners on Record Owner Occupied | Assessor + 1 DocumentUpdated Apr 2026 |
4 bd · 2.5 ba · 2,006 sqft · built 1985 · 0.343 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $195,000Nov 2001 | $7,1352025 | 2 Owners on Record Owner Occupied | AssessorUpdated Apr 2026 |
3 bd · 2.5 ba · 2,383 sqft · built 1985 · 0.344 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $266,500Oct 2012 | $7,6462025 | Amount on Record Apr 1987 | 2 Owners on Record Owner Occupied | Assessor + 1 DocumentUpdated Jul 2026 |
4 bd · 2.5 ba · 2,633 sqft · built 1986 · 0.326 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $198,000Oct 1996 | $8,8772025 | Owner on Record Owner Occupied | Assessor + 2 DocumentsUpdated Jun 2026 |
4 bd · 2.5 ba · 2,170 sqft · built 1986 · 0.403 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $182,000Aug 1995 | $7,8422025 | Amount on Record Nov 1989 | Owner on Record Owner Occupied | AssessorUpdated Jun 2026 |
3 bd · 2 ba · 1,781 sqft · built 1986 · 0.799 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $200,000Sep 2011 | $6,8172025 | —Nov 2002 | 2 Owners on Record Owner Occupied | AssessorUpdated Apr 2026 |
3 bd · 2.5 ba · 2,553 sqft · built 1985 · 2.4 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $295,000Nov 2008 | $8,9772025 | 2 Owners on Record Owner Occupied | AssessorUpdated Apr 2026 |
3 bd · 2.5 ba · 1,813 sqft · built 1984 · 1.7 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $290,000Sep 2004 | $8,6832025 | 2 Owners on Record Owner Occupied | AssessorUpdated Apr 2026 |