Middlesex County and Holliston Town property records for 6 addresses on Winston Rd, Holliston, MA · Last verified October 2026
| Properties | 6 |
|---|---|
| Median Sale Price | $1,140,000 |
| Deeds and Mortgages on File | 16 |
| Median Price per Sqft | $241 |
| Owner Occupied | 100% |
| Median Annual Tax Bill | $16,474 |
| Median Year Built | 1990 |
| Median Ownership Tenure | 3 years |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
10 Winston Rd |
4 bd · 3 ba · 3,648 sqft built 1985 · 1.16 acres | $1,147,500 Sep 2026 | $14,720 2025 | Assessor + 8 Documents Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
11 Winston Rd |
5 bd · 2.5 ba · 2,376 sqft built 1999 · 1.16 acres | $58,500 Oct 1991 | $12,974 2025 | Assessor + 1 Document Updated Jul 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
22 Winston Rd |
4 bd · 4 ba · 3,773 sqft built 1992 · 1.26 acres | $1,215,000 Apr 2025 | $16,474 2025 | Assessor + 1 Document Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
25 Winston Rd |
4 bd · 2.5 ba · 4,139 sqft built 1990 · 3.33 acres | $795,000 Oct 2018 | $17,974 2025 | Assessor + 3 Documents Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
30 Winston Rd |
4 bd · 3 ba · 3,148 sqft built 1988 · 1.31 acres | $760,000 May 2023 | $13,479 2025 | Assessor + 2 Documents Updated Jul 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
33 Winston Rd |
4 bd · 4 ba · 6,376 sqft built 1988 · 2.7 acres | $1,140,000 Nov 2021 | $23,175 2025 | Assessor + 1 Document Updated Sep 2026 | 2 Owners on File Owner Occupied |