Orange County property records for 8 addresses on Diana Dr, Winter Park, FL · Last verified August 2026
| Properties | 8 |
|---|---|
| Median Sale Price | $629,000 |
| Deeds and Mortgages on File | 6 |
| Median Price per Sqft | $290 |
| Owner Occupied | 88% |
| Median Annual Tax Bill | $9,033 |
| Median Year Built | 1966 |
| Median Ownership Tenure | 10 years |
Owner names and prior sale amounts shown locked below are available instantly with a free trial.
3 bd · 1.5 ba · 1,619 sqft · built 1953 · 0.286 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $11,7082025 | Owner on Record | AssessorUpdated May 2026 |
5 bd · 3 ba · 2,728 sqft · built 1966 · 0.252 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $280,000Dec 1993 | $5,6042025 | 2 Owners on Record Owner Occupied | AssessorUpdated May 2026 |
4 bd · 3 ba · 2,382 sqft · built 1965 · 0.286 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $6,1142025 | 2 Owners on Record Owner Occupied | AssessorUpdated May 2026 |
4 bd · 3 ba · 2,168 sqft · built 1966 · 0.275 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $629,000Jun 2016 | $9,4252025 | Amount on Record Feb 2011 | 2 Owners on Record Owner Occupied | Assessor + 2 DocumentsUpdated Aug 2026 |
4 bd · 4 ba · 2,935 sqft · built 1966 · 0.295 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,075,000Dec 2023 | $16,1742025 | Amount on Record Oct 2013 | Owner on Record Owner Occupied | Assessor + 1 DocumentUpdated May 2026 |
4 bd · 3 ba · 2,457 sqft · built 1966 · 0.295 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $360,000Jun 2000 | $7,1182025 | Amount on Record Jun 1994 | 2 Owners on Record Owner Occupied | Assessor + 1 DocumentUpdated May 2026 |
3 bd · 3 ba · 2,515 sqft · built 1965 · 0.287 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $871,000Jul 2020 | $9,0332025 | Amount on Record Apr 2012 | 2 Owners on Record Owner Occupied | Assessor + 2 DocumentsUpdated Aug 2026 |
3 bd · 2 ba · 2,195 sqft · built 1965 · 0.286 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $375,000Mar 2013 | $6,7222025 | 2 Owners on Record Owner Occupied | AssessorUpdated May 2026 |