Middlesex County and Winchester Town property records for 19 addresses on Olive St, Winchester, MA · Last verified August 2026
| Properties | 19 |
|---|---|
| Median Sale Price | $690,000 |
| Deeds and Mortgages on File | 27 |
| Median Price per Sqft | $431 |
| Owner Occupied | 84% |
| Median Annual Tax Bill | $95 |
| Median Year Built | 1963 |
| Median Ownership Tenure | 7 years |
Owner names and prior sale amounts shown locked below are available instantly with a free trial.
4 bd · 2.5 ba · 2,547 sqft · 0.339 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $350,000Jun 2002 | $1412025 | Amount on Record Dec 1996 | 2 Names on Record Owner Occupied | Assessor + 1 DocumentUpdated Apr 2026 |
3 bd · 1.5 ba · 1,306 sqft · 0.188 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $341,900May 2002 | $1002025 | 2 Names on Record Owner Occupied | AssessorUpdated Apr 2026 |
3 bd · 3 ba · 2,232 sqft · 0.186 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $810,000Jun 2020 | $1172025 | Amount on Record Nov 2001 | 1 Name on Record Owner Occupied | Assessor + 3 DocumentsUpdated Apr 2026 |
3 bd · 1 ba · 1,292 sqft · 0.276 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $690,000Jun 2023 | $912025 | 1 Name on Record | Assessor + 1 DocumentUpdated Apr 2026 |
3 bd · 1.5 ba · 1,308 sqft · 0.337 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1052025 | 2 Names on Record Owner Occupied | Assessor + 3 DocumentsUpdated Aug 2026 |
4 bd · 2.5 ba · 2,306 sqft · 0.226 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $865,000May 2021 | $1132025 | Amount on Record Feb 2006 | 2 Names on Record Owner Occupied | Assessor + 2 DocumentsUpdated Apr 2026 |
3 bd · 1 ba · 1,080 sqft · 0.225 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $125,000Jun 1991 | $932025 | 2 Names on Record Owner Occupied | AssessorUpdated Apr 2026 |
3 bd · 2 ba · 2,235 sqft · 0.182 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $952025 | 1 Name on Record Owner Occupied | AssessorUpdated Apr 2026 |
2 bd · 2 ba · 1,505 sqft · 0.233 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,000,000Aug 2025 | $9,6322025 | Amount on Record Nov 2010 | 2 Names on Record Owner Occupied | Assessor + 1 DocumentUpdated Apr 2026 |
2 bd · 1.5 ba · 1,505 sqft · 0.16 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $852025 | 1 Name on Record Owner Occupied | AssessorUpdated Apr 2026 |
3 bd · 1 ba · 958 sqft · 0.149 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $620,000Jul 2026 | $852025 | 1 Name on Record Owner Occupied | Assessor + 1 DocumentUpdated Aug 2026 |
3 bd · 1 ba · 1,624 sqft · 0.329 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1002025 | 1 Name on Record | AssessorUpdated Apr 2026 |
3 bd · 1.5 ba · 1,414 sqft · 0.219 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $882025 | 2 Names on Record Owner Occupied | Assessor + 5 DocumentsUpdated Apr 2026 |
3 bd · 2 ba · 1,642 sqft · 0.212 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $193,000Aug 1997 | $852025 | 2 Names on Record Owner Occupied | Assessor + 2 DocumentsUpdated Apr 2026 |
3 bd · 1 ba · 1,140 sqft · 0.151 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| —Jul 2014 | $802025 | —Nov 2008 | 1 Name on Record Owner Occupied | Assessor + 2 DocumentsUpdated Apr 2026 |
4 bd · 4 ba · 2,604 sqft · 0.171 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $560,000Nov 2017 | $992025 | 2 Names on Record Owner Occupied | Assessor + 2 DocumentsUpdated Apr 2026 |
3 bd · 2 ba · 1,414 sqft · 0.151 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $610,000May 2020 | $802025 | Amount on Record May 1994 | 2 Names on Record Owner Occupied | Assessor + 2 DocumentsUpdated Apr 2026 |
4 bd · 2 ba · 2,630 sqft · 0.175 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1062025 | 2 Names on Record | Assessor + 1 DocumentUpdated Aug 2026 |
3 bd · 2 ba · 1,596 sqft · 0.161 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $650,000Aug 2019 | $882025 | Amount on Record Apr 2011 | 1 Name on Record Owner Occupied | Assessor + 1 DocumentUpdated Apr 2026 |
Source: USDA Forest Service Wildfire Risk to Communities · 2nd edition (2024), fuels as of 2020
| Wildfire Risk to Homes | Not rated no burnable land in reach |
|---|---|
| Wildfire Likelihood | Negligible |
| Exposure | None beyond ember reach of burnable land |