Orange County property records for 12 addresses on Chestnut Ridge Dr, Windermere, FL · Last verified August 2026
| Properties | 12 |
|---|---|
| Median Sale Price | $3,400,000 |
| Deeds and Mortgages on File | 17 |
| Median Price per Sqft | $664 |
| Owner Occupied | 42% |
| Median Annual Tax Bill | $39,513 |
| Median Year Built | 1993 |
| Median Ownership Tenure | 5 years |
Owner names and prior sale amounts shown locked below are available instantly with a free trial.
5 bd · 5 ba · 3,776 sqft · 0.591 acres · Garage
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $75,600Apr 2011 | $13,7062025 | Amount on Record May 2006 | 2 Names on Record Owner Occupied | Assessor + 1 DocumentUpdated May 2026 |
5 bd · 6.5 ba · 6,138 sqft · 0.557 acres · Garage · Pool
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $3,400,000Dec 2021 | $64,5492025 | Amount on Record Aug 2019 | 2 Names on Record Owner Occupied | Assessor + 3 DocumentsUpdated May 2026 |
4 bd · 6.5 ba · 10,713 sqft · 2.36 acres · Garage · Pool
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $7,120,000Oct 2021 | $117,2602025 | Amount on Record Nov 2000 | 2 Names on Record Owner Occupied | Assessor + 1 DocumentUpdated May 2026 |
3 bd · 2.5 ba · 3,494 sqft · 0.5 acres · Garage · Pool
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $2,325,000Aug 2023 | $32,8302025 | Amount on Record Oct 2021 | 1 Name on Record | Assessor + 2 DocumentsUpdated May 2026 |
5 bd · 5.5 ba · 5,144 sqft · 1.86 acres · Garage · Pool
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $4,330,000Jul 2025 | $39,5132025 | Amount on Record Oct 2009 | 2 Names on Record | Assessor + 1 DocumentUpdated May 2026 |
5 bd · 6.5 ba · 6,509 sqft · 0.589 acres · Garage · Pool
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $3,100,000Dec 2024 | $42,8162025 | Amount on Record Nov 1999 | 1 Name on Record | Assessor + 2 DocumentsUpdated Jun 2026 |
5 bd · 5 ba · 5,072 sqft · 2.26 acres · Garage · Pool
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $3,500,000Nov 2016 | $76,2512025 | Amount on Record Apr 2013 | 2 Names on Record | AssessorUpdated May 2026 |
4 bd · 4 ba · 4,620 sqft · 0.542 acres · Garage · Pool
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,250,000Feb 2010 | $20,5272025 | —Oct 2000 | 2 Names on Record Owner Occupied | Assessor + 1 DocumentUpdated Aug 2026 |
5 bd · 5.5 ba · 5,724 sqft · 2.16 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $2,200,000Aug 2023 | $31,5392025 | Amount on Record Nov 2021 | 2 Names on Record | Assessor + 4 DocumentsUpdated May 2026 |
1.96 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $26,0792025 | 2 Names on Record | AssessorUpdated May 2026 |
5 bd · 6 ba · 4,917 sqft · 1.14 acres · Garage · Pool
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $3,250,000Sep 2025 | $23,4152025 | Amount on Record Jun 2004 | 2 Names on Record Owner Occupied | Assessor + 2 DocumentsUpdated May 2026 |
7 bd · 10.5 ba · 13,623 sqft · 4.03 acres · Garage · Pool
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $6,480,000Jan 1994 | $114,0082025 | 2 Names on Record | AssessorUpdated May 2026 |
Source: USDA Forest Service Wildfire Risk to Communities · 2nd edition (2024), fuels as of 2020
| Wildfire Risk | Not rated no burnable land in reach |
|---|---|
| Wildfire Likelihood | Negligible |
| Exposure | None beyond ember reach of burnable land |