Middlesex County and Winchester Town property records for 14 addresses on Chestnut St, Winchester, MA · Last verified July 2026
| Properties | 14 |
|---|---|
| Median Sale Price | $2,099,995 |
| Deeds and Mortgages on File | 27 |
| Median Price per Sqft | $492 |
| Owner Occupied | 100% |
| Median Annual Tax Bill | $276 |
| Median Year Built | 1929 |
| Median Ownership Tenure | 4 years |
Owner names and prior sale amounts shown locked below are available instantly with a free trial.
4 bd · 3.5 ba · 3,272 sqft · 0.254 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $3,450,000Jun 2025 | $15,6412025 | Amount on Record Jun 2024 | 2 Names on Record Owner Occupied | Assessor + 6 DocumentsUpdated Jul 2026 |
2 bd · 3.5 ba · 3,418 sqft · 0.298 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $19,3922025 | 1 Name on Record Owner Occupied | AssessorUpdated Apr 2026 |
6 bd · 3.5 ba · 4,827 sqft · 0.48 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,333,000Apr 2005 | $2762025 | 1 Name on Record Owner Occupied | Assessor + 1 DocumentUpdated Apr 2026 |
5 bd · 3.5 ba · 3,129 sqft · 0.3 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,900,000May 2022 | $21,1812025 | Amount on Record Mar 2000 | 2 Names on Record Owner Occupied | Assessor + 2 DocumentsUpdated Jul 2026 |
5 bd · 5 ba · 5,354 sqft · 0.375 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $2,635,000Jul 2025 | $26,6332025 | Amount on Record Jan 2024 | 1 Name on Record Owner Occupied | Assessor + 2 DocumentsUpdated Apr 2026 |
2 bd · 1.5 ba · 1,804 sqft · 0.268 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1622025 | 2 Names on Record Owner Occupied | AssessorUpdated Apr 2026 |
3 bd · 2 ba · 2,633 sqft · 0.309 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $310,000Apr 1989 | $1822025 | 2 Names on Record Owner Occupied | Assessor + 2 DocumentsUpdated Jul 2026 |
4 bd · 3.5 ba · 3,442 sqft · 0.267 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,565,000Apr 2022 | $1962025 | 2 Names on Record Owner Occupied | Assessor + 2 DocumentsUpdated Apr 2026 |
5 bd · 2.5 ba · 3,480 sqft · 0.234 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $2,075,000Jun 2024 | $2002025 | Amount on Record Aug 1993 | 1 Name on Record Owner Occupied | Assessor + 1 DocumentUpdated Apr 2026 |
4 bd · 2.5 ba · 3,498 sqft · 0.462 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,710,000Aug 2017 | $2312025 | Amount on Record Feb 1996 | 2 Names on Record Owner Occupied | Assessor + 2 DocumentsUpdated Apr 2026 |
6 bd · 4.5 ba · 6,100 sqft · 0.394 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $2,625,000Oct 2022 | $3042025 | Amount on Record Jun 2002 | 2 Names on Record Owner Occupied | Assessor + 2 DocumentsUpdated Apr 2026 |
11 bd · 3.5 ba · 4,523 sqft · 0.324 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $2,099,995Dec 2014 | $3102025 | Amount on Record Jul 2007 | 2 Names on Record Owner Occupied | Assessor + 1 DocumentUpdated Apr 2026 |
6 bd · 2.5 ba · 2,776 sqft · 0.375 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $950,000Jun 2003 | $1902025 | 1 Name on Record Owner Occupied | Assessor + 5 DocumentsUpdated Apr 2026 |
3 bd · 4 ba · 2,905 sqft · 0.194 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,075,000May 2014 | $1812025 | Amount on Record Dec 2003 | 1 Name on Record Owner Occupied | Assessor + 1 DocumentUpdated Jun 2026 |
Source: USDA Forest Service Wildfire Risk to Communities · 2nd edition (2024), fuels as of 2020
| Wildfire Risk | Low this street's cells rank at the 20th percentile of exposed land nationally · 58th in Massachusetts |
|---|---|
| Wildfire Likelihood | Low — about 1 in 10,000 per year |
| Exposure | Indirect 0 of 1 cells directly exposed |