Orange County and Chester Town property records for 7 addresses on Winding Trl, Chester, NY · Last verified October 2026
| Properties | 7 |
|---|---|
| Median Sale Price | $540,000 |
| Deeds and Mortgages on File | 11 |
| Median Price per Sqft | $242 |
| Owner Occupied | 71% |
| Median Annual Tax Bill | $14,787 |
| Median Year Built | 1990 |
| Median Ownership Tenure | 3 years |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1 Winding Trl |
3 bd · 2.5 ba · 2,040 sqft built 1991 · 1.2 acres | $540,000 Sep 2025 | $12,414 2024 | Assessor + 1 Document Updated May 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
11 Winding Trl |
4 bd · 2.5 ba · 1,834 sqft built 1990 · 1.5 acres | $445,000 Nov 2003 | $14,787 2024 | Assessor Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
21 Winding Trl |
3 bd · 2.5 ba · 1,960 sqft built 1993 · 2.3 acres | $315,000 Jul 2012 | $12,112 2024 | Assessor + 4 Documents Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
38 Winding Trl |
4 bd · 2.5 ba · 3,138 sqft built 1995 · 6.1 acres | $649,000 Apr 2023 | $16,626 2024 | Assessor + 1 Document Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
61 Winding Trl |
4 bd · 2.5 ba · 3,104 sqft built 1987 · 5.8 acres | $17,702 2024 | Assessor + 2 Documents Updated May 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
68 Winding Trl |
4 bd · 2.5 ba · 2,376 sqft built 1986 · 5.2 acres | $379,900 Oct 2016 | $16,040 2024 | Assessor + 2 Documents Updated Oct 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
71 Winding Trl |
3 bd · 2.5 ba · 2,610 sqft built 1987 · 6.4 acres | $670,000 Jun 2024 | $14,680 2024 | Assessor + 1 Document Updated Oct 2026 | 2 Owners on File |