Orange County property records for 22 addresses on Winchester Dr, Winter Park, FL · Last verified August 2026
| Properties | 22 |
|---|---|
| Median Sale Price | $1,395,000 |
| Deeds and Mortgages on File | 20 |
| Median Price per Sqft | $492 |
| Owner Occupied | 82% |
| Median Annual Tax Bill | $10,311 |
| Median Year Built | 1958 |
| Median Ownership Tenure | 10 years |
Owner names and prior sale amounts shown locked below are available instantly with a free trial.
3 bd · 2.5 ba · 2,238 sqft · built 1959 · 0.31 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $809,000Apr 2021 | $10,5792025 | Amount on Record Jul 2016 | 2 Names on Record Owner Occupied | Assessor + 1 DocumentUpdated May 2026 |
4 bd · 2.5 ba · 2,934 sqft · built 1964 · 0.31 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $6,2222025 | 2 Names on Record Owner Occupied | Assessor + 1 DocumentUpdated May 2026 |
4 bd · 3.5 ba · 2,535 sqft · built 1960 · 0.272 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $820,000Jun 2017 | $12,1672025 | Amount on Record Jan 2006 | 1 Name on Record Owner Occupied | Assessor + 1 DocumentUpdated May 2026 |
5 bd · 3 ba · 3,030 sqft · built 1967 · 0.253 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $549,000Jan 2016 | $8,1812025 | 2 Names on Record | Assessor + 1 DocumentUpdated May 2026 |
3 bd · 4 ba · 2,834 sqft · built 2013 · 0.308 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $300,000May 2012 | $13,0422025 | —Sep 2005 | 2 Names on Record Owner Occupied | Assessor + 2 DocumentsUpdated May 2026 |
4 bd · 2 ba · 2,461 sqft · built 1958 · 0.275 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $3,000,000Aug 2025 | $8,1712025 | Amount on Record Mar 2023 | 2 Names on Record | Assessor + 1 DocumentUpdated May 2026 |
5 bd · 3 ba · 2,747 sqft · built 1958 · 0.3 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $430,000Dec 2010 | $8,2842025 | 2 Names on Record Owner Occupied | AssessorUpdated May 2026 |
4 bd · 3 ba · 2,637 sqft · built 1960 · 0.275 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,400,000Jul 2025 | $17,7382025 | Amount on Record Aug 2023 | 1 Name on Record Owner Occupied | Assessor + 1 DocumentUpdated May 2026 |
3 bd · 3.5 ba · 2,414 sqft · built 1957 · 0.299 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $360,000Jun 2012 | $7,6042025 | —Jan 2006 | 2 Names on Record Owner Occupied | AssessorUpdated May 2026 |
4 bd · 3 ba · 2,289 sqft · built 1958 · 0.275 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $220,000Jul 2001 | $5,9592025 | 1 Name on Record Owner Occupied | AssessorUpdated May 2026 |
4 bd · 3.5 ba · 2,516 sqft · built 1957 · 0.299 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,395,000Mar 2025 | $16,7262025 | Amount on Record Sep 2023 | 2 Names on Record Owner Occupied | Assessor + 4 DocumentsUpdated Aug 2026 |
3 bd · 2.5 ba · 2,301 sqft · built 1957 · 0.275 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $239,900Oct 1998 | $10,3112025 | 2 Names on Record Owner Occupied | AssessorUpdated May 2026 |
4 bd · 2 ba · 2,072 sqft · built 1958 · 0.298 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| —Nov 2001 | $6,5552025 | Amount on Record Jul 1997 | 1 Name on Record | AssessorUpdated Jul 2026 |
4 bd · 3.5 ba · 3,322 sqft · built 1958 · 0.298 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $535,000Nov 2013 | $11,1272025 | Amount on Record Jul 1997 | 2 Names on Record Owner Occupied | AssessorUpdated May 2026 |
3 bd · 3 ba · 2,253 sqft · built 1957 · 0.275 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $5,0392025 | 2 Names on Record Owner Occupied | Assessor + 1 DocumentUpdated May 2026 |
4 bd · 2 ba · 2,722 sqft · built 1957 · 0.298 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $530,000Dec 2011 | $8,6362025 | —Jul 2010 | 2 Names on Record Owner Occupied | Assessor + 2 DocumentsUpdated Jul 2026 |
5 bd · 4.5 ba · 3,442 sqft · built 2021 · 0.275 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $460,000Aug 2018 | $25,5042025 | 2 Names on Record Owner Occupied | Assessor + 2 DocumentsUpdated May 2026 |
5 bd · 4.75 ba · 4,080 sqft · built 2023 · 0.297 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $675,000Feb 2022 | $26,0832025 | —Jul 2021 | 2 Names on Record Owner Occupied | Assessor + 1 DocumentUpdated May 2026 |
4 bd · 3 ba · 2,607 sqft · built 1957 · 0.275 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $560,000Jul 2013 | $14,6692025 | Amount on Record Dec 2005 | 2 Names on Record Owner Occupied | AssessorUpdated May 2026 |
4 bd · 2 ba · 3,421 sqft · built 1957 · 0.297 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,685,000May 2025 | $15,9222025 | Amount on Record Dec 2000 | 2 Names on Record Owner Occupied | AssessorUpdated May 2026 |
3 bd · 2 ba · 2,226 sqft · built 1958 · 0.275 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $242,200Apr 2019 | $8,7482025 | Amount on Record May 2015 | 2 Names on Record Owner Occupied | Assessor + 2 DocumentsUpdated May 2026 |
4 bd · 2.5 ba · 2,630 sqft · built 1957 · 0.352 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $620,000Jun 2015 | $5,0382025 | Amount on Record Oct 2003 | 2 Names on Record | AssessorUpdated May 2026 |
Source: USDA Forest Service Wildfire Risk to Communities · 2nd edition (2024), fuels as of 2020
| Wildfire Risk | Low this street's cells rank above 4% of the US · above 4% of Florida |
|---|---|
| Wildfire Likelihood | Less than 1 in 10,000 per year |
| Exposure | Direct 1 of 2 cells directly exposed · 1 adjoin burnable vegetation |