Orange County property records for 22 addresses on Highland Rd, Winter Park, FL · Last verified August 2026
| Properties | 22 |
|---|---|
| Median Sale Price | $1,825,000 |
| Deeds and Mortgages on File | 39 |
| Median Price per Sqft | $518 |
| Owner Occupied | 73% |
| Median Annual Tax Bill | $14,259 |
| Median Year Built | 1949 |
| Median Ownership Tenure | 9 years |
Owner names and prior sale amounts shown locked below are available instantly with a free trial.
6 bd · 4.5 ba · 4,234 sqft · built 1925 · 0.86 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $16,4352025 | 2 Names on Record Owner Occupied | Assessor + 1 DocumentUpdated May 2026 |
3 bd · 1.5 ba · 1,752 sqft · built 1947 · 0.312 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $324,300Jan 2010 | $10,0752025 | —Sep 2001 | 2 Names on Record | AssessorUpdated May 2026 |
4 bd · 3.5 ba · 3,196 sqft · built 1998 · 0.312 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $9,8972025 | 2 Names on Record | Assessor + 1 DocumentUpdated May 2026 |
4 bd · 4.5 ba · 3,977 sqft · built 2020 · 0.312 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,825,000Oct 2020 | $33,5412025 | Amount on Record Aug 2018 | 2 Names on Record Owner Occupied | Assessor + 4 DocumentsUpdated May 2026 |
3 bd · 3 ba · 2,018 sqft · built 1968 · 0.312 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $6,1482025 | 2 Names on Record Owner Occupied | Assessor + 1 DocumentUpdated Jul 2026 |
4 bd · 3.5 ba · 2,584 sqft · built 1923 · 0.332 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $720,000Jan 2016 | $11,4272025 | Amount on Record Jul 2013 | 1 Name on Record Owner Occupied | Assessor + 2 DocumentsUpdated May 2026 |
5 bd · 6 ba · 4,433 sqft · built 2007 · 0.332 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $2,300,000Dec 2022 | $28,6342025 | Amount on Record May 2021 | 2 Names on Record Owner Occupied | Assessor + 3 DocumentsUpdated May 2026 |
4 bd · 3 ba · 3,276 sqft · built 1948 · 0.312 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $225,000Jun 1993 | $6,7372025 | 2 Names on Record Owner Occupied | Assessor + 2 DocumentsUpdated May 2026 |
3 bd · 2 ba · 2,193 sqft · built 1949 · 0.312 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,156,000Aug 2023 | $14,4702025 | Amount on Record Apr 2023 | 2 Names on Record Owner Occupied | Assessor + 3 DocumentsUpdated May 2026 |
4 bd · 3.5 ba · 2,757 sqft · built 1925 · 0.504 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $82,000Jan 2003 | $7,7952025 | Amount on Record Dec 2000 | 2 Names on Record Owner Occupied | AssessorUpdated May 2026 |
3 bd · 2 ba · 1,689 sqft · built 1967 · 0.281 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $385,000Aug 2002 | $5,9212025 | Amount on Record Sep 2000 | 2 Names on Record Owner Occupied | Assessor + 5 DocumentsUpdated May 2026 |
10 bd · 13.25 ba · 9,733 sqft · built 2018 · 0.412 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $610,000Jul 2017 | $29,3842025 | 2 Names on Record Owner Occupied | Assessor + 2 DocumentsUpdated May 2026 |
4 bd · 3.5 ba · 3,154 sqft · built 1919 · 0.343 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $350,000Apr 2000 | $6,6842025 | 2 Names on Record Owner Occupied | Assessor + 1 DocumentUpdated May 2026 |
4 bd · 3.5 ba · 3,058 sqft · built 1948 · 0.458 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $832,000Mar 2019 | $14,2592025 | Amount on Record Apr 2000 | 2 Names on Record Owner Occupied | Assessor + 3 DocumentsUpdated May 2026 |
3 bd · 4 ba · 3,043 sqft · built 1919 · 0.31 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $6,000Jan 1998 | $3,3162025 | 2 Names on Record Owner Occupied | AssessorUpdated May 2026 |
10 bd · 12.25 ba · 12,496 sqft · built 2008 · 0.458 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $2,200,000Apr 2019 | $41,1832025 | Amount on Record May 2006 | 2 Names on Record | Assessor + 1 DocumentUpdated May 2026 |
3 bd · 2 ba · 1,398 sqft · built 1941 · 0.152 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $857,500Jan 2025 | $7,2752025 | Amount on Record Jun 2020 | 2 Names on Record | Assessor + 2 DocumentsUpdated May 2026 |
3 bd · 2 ba · 1,994 sqft · built 1941 · 0.154 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $475,000Apr 2018 | $6,5702025 | Amount on Record Nov 2013 | 1 Name on Record Owner Occupied | Assessor + 2 DocumentsUpdated May 2026 |
4 bd · 3.5 ba · 4,001 sqft · built 1948 · 0.687 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $909,600May 2017 | $14,8562025 | 2 Names on Record Owner Occupied | Assessor + 2 DocumentsUpdated May 2026 |
5 bd · 5.75 ba · 4,350 sqft · built 2023 · 0.257 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $3,000,000Sep 2024 | $25,7972025 | Amount on Record Nov 2022 | 1 Name on Record | Assessor + 2 DocumentsUpdated Aug 2026 |
5 bd · 4 ba · 3,727 sqft · built 2022 · 0.341 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $495,000Aug 2020 | $22,9122025 | Amount on Record Jun 2011 | 2 Names on Record Owner Occupied | Assessor + 2 DocumentsUpdated May 2026 |
6 bd · 7.25 ba · 6,062 sqft · built 2011 · 0.255 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $322,500Nov 2007 | $24,9082025 | 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 19% of the US · above 6% of Florida |
|---|---|
| Wildfire Likelihood | About 1 in 3,896 per year |
| Exposure | Direct 2 of 3 cells directly exposed · 3 adjoin burnable vegetation |