Middlesex County and Winchester Town property records for 41 addresses on Woodside Rd, Winchester, MA · Last verified October 2026
| Properties | 41 |
|---|---|
| Median Sale Price | $1,549,000 |
| Deeds and Mortgages on File | 75 |
| Median Price per Sqft | $598 |
| Owner Occupied | 100% |
| Median Annual Tax Bill | $147 |
| Median Year Built | 1928 |
| Median Ownership Tenure | 12 years |
Owner names and prior sale amounts shown locked below are available instantly with a free trial.
6 bd · 3.5 ba · 4,710 sqft · built 1895 · 0.276 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,300,000Oct 2018 | $21,5442026 | Amount on Record May 2017 | 2 Owners on Record Owner Occupied | Assessor + 5 DocumentsUpdated Oct 2026 |
5 bd · 3.5 ba · 3,233 sqft · built 1913 · 0.468 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $425,000May 1997 | $20,2642026 | Owner on Record Owner Occupied | Assessor + 1 DocumentUpdated Oct 2026 |
6 bd · 1.5 ba · 3,401 sqft · built 1910 · 0.792 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $2,224,000Apr 2025 | $21,2972025 | Owner on Record Owner Occupied | Assessor + 1 DocumentUpdated Apr 2026 |
4 bd · 2.5 ba · 2,420 sqft · built 1927 · 0.313 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $389,500Jun 1997 | $17,0212026 | Amount on Record Jan 1989 | 2 Owners on Record Owner Occupied | Assessor + 1 DocumentUpdated Oct 2026 |
5 bd · 4.5 ba · 4,530 sqft · built 1910 · 0.507 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $27,8872026 | 2 Owners on Record Owner Occupied | AssessorUpdated Oct 2026 |
3 bd · 1.5 ba · 1,966 sqft · built 1930 · 0.27 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $24,000Jun 1966 | $14,7922026 | 2 Owners on Record Owner Occupied | AssessorUpdated Oct 2026 |
3 bd · 3 ba · 2,079 sqft · built 1928 · 0.266 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,035,000Oct 2019 | $16,0332026 | —Jan 2012 | 2 Owners on Record Owner Occupied | Assessor + 2 DocumentsUpdated Oct 2026 |
4 bd · 2.5 ba · 3,003 sqft · built 1906 · 0.299 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,800,000Jul 2023 | $19,6712026 | Amount on Record Jul 1999 | 2 Owners on Record Owner Occupied | Assessor + 3 DocumentsUpdated Oct 2026 |
4 bd · 2.5 ba · 3,537 sqft · built 1990 · 0.636 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $619,000Apr 1992 | $2662025 | Amount on Record Oct 1990 | 2 Owners on Record Owner Occupied | AssessorUpdated Apr 2026 |
4 bd · 3 ba · 2,722 sqft · built 1910 · 0.505 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| —Jan 2007 | $16,6282026 | 2 Owners on Record Owner Occupied | Assessor + 1 DocumentUpdated Oct 2026 |
3 bd · 1.5 ba · 1,613 sqft · built 1917 · 0.539 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $175,000Aug 2017 | $13,3782025 | 2 Owners on Record Owner Occupied | Assessor + 2 DocumentsUpdated Jul 2026 |
3 bd · 2.5 ba · 2,587 sqft · built 1933 · 0.415 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,549,000Dec 2025 | $14,5962026 | Amount on Record Nov 2024 | 2 Owners on Record Owner Occupied | Assessor + 6 DocumentsUpdated Oct 2026 |
3 bd · 3 ba · 2,596 sqft · built 1935 · 0.247 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $13,7472025 | 2 Owners on Record Owner Occupied | Assessor + 1 DocumentUpdated Apr 2026 |
3 bd · 1 ba · 1,500 sqft · built 1927 · 0.249 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $176,000Dec 1986 | $11,4992026 | Owner on Record Owner Occupied | AssessorUpdated Oct 2026 |
3 bd · 1.5 ba · 1,694 sqft · built 1922 · 0.263 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $699,000Jun 2016 | $14,1112026 | Amount on Record Apr 1997 | 2 Owners on Record Owner Occupied | Assessor + 3 DocumentsUpdated Oct 2026 |
3 bd · 2.5 ba · 1,554 sqft · built 1915 · 0.307 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $485,000Feb 2003 | $14,2002026 | 2 Owners on Record Owner Occupied | AssessorUpdated Oct 2026 |
5 bd · 3.5 ba · 3,289 sqft · built 1927 · 0.153 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $2,100,000Jun 2022 | $20,8152026 | —Jan 2012 | 2 Owners on Record Owner Occupied | Assessor + 7 DocumentsUpdated Oct 2026 |
3 bd · 3.5 ba · 2,515 sqft · built 1933 · 0.157 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $872,500Jul 2020 | $15,3192026 | —Mar 2006 | 2 Owners on Record Owner Occupied | Assessor + 3 DocumentsUpdated Oct 2026 |
4 bd · 2.5 ba · 2,376 sqft · built 1930 · 0.184 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $215,000Mar 1990 | $1462025 | Owner on Record Owner Occupied | Assessor + 2 DocumentsUpdated Apr 2026 |
3 bd · 1.5 ba · 1,878 sqft · built 1930 · 0.313 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $608,200Feb 2014 | $14,7832026 | 2 Owners on Record Owner Occupied | Assessor + 1 DocumentUpdated Oct 2026 |
5 bd · 3.5 ba · 2,630 sqft · built 1925 · 0.278 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,530,000Nov 2021 | $17,3152026 | Amount on Record Jul 1999 | 2 Owners on Record Owner Occupied | Assessor + 2 DocumentsUpdated Oct 2026 |
4 bd · 3.5 ba · 3,453 sqft · built 1931 · 0.261 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $445,000Oct 1999 | $1492025 | 2 Owners on Record Owner Occupied | Assessor + 3 DocumentsUpdated Apr 2026 |
3 bd · 2.5 ba · 4,143 sqft · built 1930 · 0.293 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $220,000Jan 1994 | $19,1192026 | 2 Owners on Record Owner Occupied | Assessor + 2 DocumentsUpdated Oct 2026 |
5 bd · 2.5 ba · 2,546 sqft · built 1930 · 0.242 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,550,000Jun 2023 | $15,3442026 | Amount on Record Jan 2002 | 2 Owners on Record Owner Occupied | Assessor + 1 DocumentUpdated Oct 2026 |
3 bd · 1.5 ba · 1,235 sqft · built 1930 · 0.269 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $395,000Jun 2000 | $13,2372026 | Amount on Record Jul 1992 | 2 Owners on Record Owner Occupied | Assessor + 1 DocumentUpdated Oct 2026 |
3 bd · 2.5 ba · 2,610 sqft · built 1929 · 0.229 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $930,000Jun 2019 | $14,3982026 | Amount on Record Aug 1993 | 2 Owners on Record Owner Occupied | Assessor + 3 DocumentsUpdated Oct 2026 |
3 bd · 2.5 ba · 2,887 sqft · built 1931 · 0.206 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,650,000Nov 2024 | $16,6492026 | Amount on Record Jul 2018 | Owner on Record Owner Occupied | Assessor + 3 DocumentsUpdated Oct 2026 |
3 bd · 1.5 ba · 1,552 sqft · built 1927 · 0.178 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $45,000Oct 1975 | $13,3152026 | 2 Owners on Record Owner Occupied | AssessorUpdated Oct 2026 |
3 bd · 2.5 ba · 1,912 sqft · built 1927 · 0.161 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $580,000Sep 2014 | $12,8762026 | Amount on Record May 2002 | 2 Owners on Record Owner Occupied | AssessorUpdated Oct 2026 |
4 bd · 1.5 ba · 2,566 sqft · built 1930 · 0.153 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,200,000Aug 2025 | $13,4162026 | 2 Owners on Record Owner Occupied | Assessor + 1 DocumentUpdated Oct 2026 |
3 bd · 1.5 ba · 1,664 sqft · built 1927 · 0.163 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $948,800Jun 2024 | $11,4092026 | Owner on Record Owner Occupied | Assessor + 1 DocumentUpdated Oct 2026 |
4 bd · 2.5 ba · 2,736 sqft · built 1930 · 0.154 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $147,000Mar 1985 | $13,3312026 | 2 Owners on Record Owner Occupied | Assessor + 3 DocumentsUpdated Oct 2026 |
3 bd · 2.5 ba · 1,984 sqft · built 1927 · 0.148 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| —Jan 2017 | $1312025 | Amount on Record Jan 1991 | Owner on Record Owner Occupied | Assessor + 1 DocumentUpdated Apr 2026 |
3 bd · 2 ba · 1,552 sqft · built 1920 · 0.151 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,080,000May 2026 | $13,0172026 | Amount on Record Nov 1998 | Owner on Record Owner Occupied | Assessor + 2 DocumentsUpdated Oct 2026 |
4 bd · 2.5 ba · 3,320 sqft · built 1926 · 0.144 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $700,000May 2012 | $17,8492026 | Amount on Record Jun 2003 | Owner on Record Owner Occupied | Assessor + 3 DocumentsUpdated Oct 2026 |
4 bd · 1.5 ba · 1,786 sqft · built 1930 · 0.157 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $84,000Oct 1980 | $12,9122026 | Owner on Record Owner Occupied | AssessorUpdated Oct 2026 |
3 bd · 2.5 ba · 2,129 sqft · built 1927 · 0.141 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $727,000Aug 2017 | $13,2612026 | —Dec 2010 | 2 Owners on Record Owner Occupied | Assessor + 3 DocumentsUpdated Oct 2026 |
4 bd · 2.5 ba · 2,218 sqft · built 1930 · 0.163 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $900,000Oct 2018 | $14,1922026 | Amount on Record May 1963 | 2 Owners on Record Owner Occupied | Assessor + 3 DocumentsUpdated Oct 2026 |
3 bd · 2.5 ba · 1,754 sqft · built 1928 · 0.139 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $190,000Jan 1994 | $13,2392026 | 2 Owners on Record Owner Occupied | Assessor + 2 DocumentsUpdated Oct 2026 |
4 bd · 2 ba · 2,994 sqft · built 1948 · 0.37 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $827,775Dec 2014 | $14,8362026 | Amount on Record Jun 2004 | 2 Owners on Record Owner Occupied | Assessor + 1 DocumentUpdated Oct 2026 |
3 bd · 1.5 ba · 1,795 sqft · built 1952 · 0.23 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $44,500Jun 1977 | $1012025 | 2 Owners on Record Owner Occupied | Assessor + 1 DocumentUpdated Apr 2026 |