Middlesex County and Winchester Town property records for 13 addresses on Pepper Hill Dr, Winchester, MA · Last verified October 2026
| Properties | 13 |
|---|---|
| Median Sale Price | $730,000 |
| Deeds and Mortgages on File | 12 |
| Median Price per Sqft | $233 |
| Owner Occupied | 85% |
| Median Annual Tax Bill | $175 |
| Median Year Built | 1977 |
| Median Ownership Tenure | 20 years |
Owner names and prior sale amounts shown locked below are available instantly with a free trial.
4 bd · 3 ba · 3,951 sqft · built 2004 · 0.459 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $2272025 | 2 Owners on Record | AssessorUpdated Apr 2026 |
7 bd · 6.5 ba · 7,377 sqft · built 1976 · 0.459 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $302,000Dec 2000 | $2272025 | 2 Owners on Record Owner Occupied | Assessor + 1 DocumentUpdated Apr 2026 |
4 bd · 5 ba · 6,103 sqft · built 1972 · 0.459 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $730,000Nov 2006 | $2142025 | Amount on Record Apr 2002 | Owner on Record Owner Occupied | Assessor + 2 DocumentsUpdated Aug 2026 |
4 bd · 2.5 ba · 4,198 sqft · built 1977 · 0.459 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1712025 | 2 Owners on Record Owner Occupied | AssessorUpdated Apr 2026 |
4 bd · 2.5 ba · 2,801 sqft · built 1975 · 0.635 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $380,000Mar 1996 | $1602025 | 2 Owners on Record Owner Occupied | AssessorUpdated Jul 2026 |
4 bd · 3 ba · 3,800 sqft · built 1971 · 0.537 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,894,100Feb 2025 | $17,4232025 | —Nov 2018 | 2 Owners on Record Owner Occupied | Assessor + 1 DocumentUpdated Apr 2026 |
3 bd · 3 ba · 2,659 sqft · built 1973 · 0.459 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $450,000Sep 1997 | $1682025 | 2 Owners on Record Owner Occupied | AssessorUpdated Apr 2026 |
4 bd · 3.5 ba · 3,029 sqft · built 1977 · 0.464 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,105,000Nov 2016 | $1742025 | Amount on Record Aug 1991 | 2 Owners on Record Owner Occupied | Assessor + 3 DocumentsUpdated Apr 2026 |
4 bd · 2.5 ba · 3,213 sqft · built 1973 · 0.459 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1692025 | Owner on Record Owner Occupied | AssessorUpdated Apr 2026 |
3 bd · 2.5 ba · 3,369 sqft · built 1977 · 0.467 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| —Jun 2018 | $1752025 | 2 Owners on Record Owner Occupied | Assessor + 2 DocumentsUpdated Apr 2026 |
4 bd · 3 ba · 2,865 sqft · built 1977 · 0.459 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $668,000Jul 2003 | $1692025 | 2 Owners on Record Owner Occupied | Assessor + 1 DocumentUpdated Apr 2026 |
4 bd · 3.5 ba · 2,600 sqft · built 1977 · 0.538 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1792025 | 2 Owners on Record Owner Occupied | Assessor + 1 DocumentUpdated Apr 2026 |
5 bd · 3.5 ba · 3,576 sqft · built 2010 · 0.159 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,430,000Nov 2020 | $19,6502026 | Amount on Record May 2010 | 2 Owners on Record | Assessor + 1 DocumentUpdated Oct 2026 |