Middlesex County and Winchester Town property records for 30 addresses on Pilgrim Dr, Winchester, MA · Last verified July 2026
| Properties | 30 |
|---|---|
| Median Sale Price | $1,775,000 |
| Deeds and Mortgages on File | 40 |
| Median Price per Sqft | $524 |
| Owner Occupied | 100% |
| Median Annual Tax Bill | $167 |
| Median Year Built | 1962 |
| Median Ownership Tenure | 17 years |
Owner names and prior sale amounts shown locked below are available instantly with a free trial.
4 bd · 3.5 ba · 2,957 sqft · 0.909 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $231,000Nov 1983 | $1692025 | 2 Names on Record Owner Occupied | Assessor + 2 DocumentsUpdated Apr 2026 |
4 bd · 2.5 ba · 2,725 sqft · 0.714 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $675,000Nov 2007 | $1602025 | 2 Names on Record Owner Occupied | AssessorUpdated Apr 2026 |
5 bd · 6.5 ba · 5,253 sqft · 0.944 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $2,155,000Feb 2021 | $28,5112025 | Amount on Record Jan 2020 | 2 Names on Record Owner Occupied | Assessor + 4 DocumentsUpdated Apr 2026 |
3 bd · 2 ba · 2,223 sqft · 0.38 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $195,000Nov 1984 | $1472025 | 2 Names on Record Owner Occupied | Assessor + 1 DocumentUpdated Apr 2026 |
6 bd · 3.5 ba · 4,138 sqft · 0.363 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $2,400,000Oct 2024 | $22,2862025 | Amount on Record Jul 2019 | 1 Name on Record Owner Occupied | Assessor + 3 DocumentsUpdated Apr 2026 |
3 bd · 2.5 ba · 2,738 sqft · 0.456 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $853,000Jun 2013 | $1672025 | Amount on Record Aug 2001 | 2 Names on Record Owner Occupied | Assessor + 1 DocumentUpdated Apr 2026 |
3 bd · 2.5 ba · 1,822 sqft · 0.356 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $277,500Jun 1993 | $1402025 | 2 Names on Record Owner Occupied | Assessor + 1 DocumentUpdated Apr 2026 |
3 bd · 2.5 ba · 2,541 sqft · 0.374 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,725,000Sep 2025 | $15,7192025 | Amount on Record Jun 2017 | 2 Names on Record Owner Occupied | Assessor + 4 DocumentsUpdated Apr 2026 |
4 bd · 3 ba · 3,772 sqft · 0.507 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $415,000Oct 1996 | $2052025 | 2 Names on Record Owner Occupied | Assessor + 1 DocumentUpdated Apr 2026 |
4 bd · 3 ba · 2,750 sqft · 0.456 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $385,000Aug 1994 | $1582025 | 2 Names on Record Owner Occupied | AssessorUpdated Apr 2026 |
5 bd · 2.5 ba · 4,653 sqft · 0.533 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $78,500Aug 1976 | $1932025 | 2 Names on Record Owner Occupied | Assessor + 2 DocumentsUpdated Apr 2026 |
4 bd · 3.5 ba · 3,575 sqft · 0.385 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,875,000May 2023 | $1772025 | Amount on Record Mar 2002 | 2 Names on Record Owner Occupied | Assessor + 4 DocumentsUpdated Apr 2026 |
4 bd · 2.5 ba · 2,840 sqft · 0.515 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $899,000Mar 2001 | $1592025 | Amount on Record Nov 1997 | 2 Names on Record Owner Occupied | Assessor + 1 DocumentUpdated Apr 2026 |
4 bd · 2.5 ba · 2,940 sqft · 0.433 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $790,000Sep 2016 | $1522025 | Amount on Record Jul 2003 | 2 Names on Record Owner Occupied | Assessor + 1 DocumentUpdated Apr 2026 |
5 bd · 3.5 ba · 3,078 sqft · 0.474 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,775,000Aug 2025 | $18,8272025 | Amount on Record Jun 2015 | 2 Names on Record Owner Occupied | Assessor + 2 DocumentsUpdated Jul 2026 |
3 bd · 4.5 ba · 4,207 sqft · 0.36 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,382,500May 2007 | $2152025 | 2 Names on Record Owner Occupied | Assessor + 1 DocumentUpdated Apr 2026 |
4 bd · 4.5 ba · 6,076 sqft · 0.513 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,330,000Feb 2006 | $2152025 | Amount on Record Nov 1989 | 2 Names on Record Owner Occupied | AssessorUpdated Apr 2026 |
4 bd · 3 ba · 3,196 sqft · 0.698 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $775,000Jun 2010 | $1672025 | Amount on Record May 1997 | 2 Names on Record Owner Occupied | Assessor + 1 DocumentUpdated Apr 2026 |
4 bd · 3 ba · 2,780 sqft · 0.725 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $700,000Jan 2009 | $1652025 | 2 Names on Record Owner Occupied | AssessorUpdated Apr 2026 |
4 bd · 3.5 ba · 3,223 sqft · 0.624 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $325,000Oct 1992 | $1672025 | 1 Name on Record Owner Occupied | AssessorUpdated Apr 2026 |
4 bd · 3 ba · 3,103 sqft · 0.484 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| —Aug 2018 | $1652025 | Amount on Record May 2011 | 2 Names on Record Owner Occupied | Assessor + 1 DocumentUpdated Apr 2026 |
4 bd · 3.5 ba · 3,409 sqft · 0.56 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $430,000Jun 1998 | $16,1492025 | Amount on Record Aug 1993 | 2 Names on Record Owner Occupied | Assessor + 2 DocumentsUpdated Jul 2026 |
4 bd · 3 ba · 3,271 sqft · 0.468 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,700,000Jun 2026 | $1692025 | Amount on Record Jul 1994 | 2 Names on Record Owner Occupied | Assessor + 1 DocumentUpdated Jul 2026 |
4 bd · 3 ba · 2,670 sqft · 0.473 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1512025 | 2 Names on Record Owner Occupied | AssessorUpdated Apr 2026 |
5 bd · 3 ba · 2,634 sqft · 0.483 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $912,500Oct 2017 | $1602025 | —Mar 2017 | 2 Names on Record Owner Occupied | Assessor + 4 DocumentsUpdated Apr 2026 |
4 bd · 2.5 ba · 3,365 sqft · 0.528 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $800,000Aug 2005 | $1752025 | Amount on Record Jun 2005 | 2 Names on Record Owner Occupied | AssessorUpdated Apr 2026 |
4 bd · 3.5 ba · 3,799 sqft · 0.609 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| —Aug 2018 | $1742025 | 2 Names on Record Owner Occupied | Assessor + 1 DocumentUpdated Apr 2026 |
4 bd · 2.5 ba · 2,154 sqft · 0.615 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $765,000Jun 2004 | $1602025 | Amount on Record Jul 1997 | 2 Names on Record Owner Occupied | AssessorUpdated Apr 2026 |
5 bd · 3 ba · 3,259 sqft · 0.682 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $763,430Aug 2013 | $1572025 | 2 Names on Record Owner Occupied | AssessorUpdated Jul 2026 |
4 bd · 2.5 ba · 2,436 sqft · 0.619 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $959,000May 2016 | $1622025 | 2 Names on Record Owner Occupied | Assessor + 2 DocumentsUpdated Apr 2026 |