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 |
Owner names and exact recorded amounts are on file and can be viewed instantly on this page with a free 10-day trial.
3 bd · 2.5 ba · 2,040 sqft · built 1991 · 1.2 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $540,000Sep 2025 | $12,4142024 | Owner on Record | Assessor + 1 DocumentUpdated May 2026 |
4 bd · 2.5 ba · 1,834 sqft · built 1990 · 1.5 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $445,000Nov 2003 | $14,7872024 | 2 Owners on Record Owner Occupied | AssessorUpdated May 2026 |
3 bd · 2.5 ba · 1,960 sqft · built 1993 · 2.3 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $315,000Jul 2012 | $12,1122024 | 2 Owners on Record Owner Occupied | Assessor + 4 DocumentsUpdated Oct 2026 |
4 bd · 2.5 ba · 3,138 sqft · built 1995 · 6.1 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $649,000Apr 2023 | $16,6262024 | Amount on Record Dec 1995 | 2 Owners on Record Owner Occupied | Assessor + 1 DocumentUpdated Oct 2026 |
4 bd · 2.5 ba · 3,104 sqft · built 1987 · 5.8 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $17,7022024 | Owner on Record Owner Occupied | Assessor + 2 DocumentsUpdated May 2026 |
4 bd · 2.5 ba · 2,376 sqft · built 1986 · 5.2 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $379,900Oct 2016 | $16,0402024 | Owner on Record Owner Occupied | Assessor + 2 DocumentsUpdated Oct 2026 |
3 bd · 2.5 ba · 2,610 sqft · built 1987 · 6.4 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $670,000Jun 2024 | $14,6802024 | Amount on Record Jan 2016 | 2 Owners on Record | Assessor + 1 DocumentUpdated Oct 2026 |