Orange County property records for 16 addresses on Hillcrest Ave, Winter Park, FL · Last verified July 2026
| Properties | 16 |
|---|---|
| Median Sale Price | $1,500,000 |
| Deeds and Mortgages on File | 28 |
| Median Price per Sqft | $471 |
| Owner Occupied | 75% |
| Median Annual Tax Bill | $18,826 |
| Median Year Built | 2008 |
| Median Ownership Tenure | 6 years |
Owner names and prior sale amounts shown locked below are available instantly with a free trial.
3 bd · 2.5 ba · 2,929 sqft · built 1935 · 0.417 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $50,000Jul 1996 | $7,2102025 | 1 Name on Record Owner Occupied | Assessor + 1 DocumentUpdated May 2026 |
3 bd · 3.5 ba · 2,916 sqft · built 2008 · 0.192 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $840,000Nov 2011 | $14,5982025 | Amount on Record Jul 2006 | 2 Names on Record | Assessor + 2 DocumentsUpdated May 2026 |
4 bd · 3.5 ba · 2,907 sqft · built 2016 · 0.192 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,602,000May 2022 | $23,9172025 | Amount on Record Dec 2014 | 2 Names on Record Owner Occupied | Assessor + 1 DocumentUpdated May 2026 |
3 bd · 2 ba · 1,814 sqft · built 1954 · 0.352 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $687,500Feb 2020 | $9,2162025 | Amount on Record Apr 2019 | 1 Name on Record | Assessor + 1 DocumentUpdated May 2026 |
4 bd · 3.5 ba · 3,037 sqft · built 1930 · 0.24 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,500,000Oct 2020 | $21,4422025 | Amount on Record Jul 2014 | 2 Names on Record Owner Occupied | Assessor + 1 DocumentUpdated May 2026 |
10 bd · 10.25 ba · 8,725 sqft · built 2010 · 0.336 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,385,000Aug 2010 | $20,5152025 | Amount on Record Jan 2010 | 2 Names on Record Owner Occupied | Assessor + 1 DocumentUpdated May 2026 |
8 bd · 8.25 ba · 7,585 sqft · built 2013 · 0.337 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,550,000Oct 2019 | $24,2412025 | Amount on Record Sep 2013 | 2 Names on Record Owner Occupied | Assessor + 3 DocumentsUpdated May 2026 |
10 bd · 11.25 ba · 7,486 sqft · built 2018 · 0.24 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $410,000May 2017 | $18,8262025 | Amount on Record Jan 2012 | 2 Names on Record Owner Occupied | Assessor + 3 DocumentsUpdated May 2026 |
3 bd · 1.5 ba · 1,859 sqft · built 1930 · 0.192 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $25,000Nov 2007 | $4,5172025 | Amount on Record Dec 1998 | 1 Name on Record Owner Occupied | AssessorUpdated May 2026 |
3 bd · 2.5 ba · 2,662 sqft · built 1947 · 0.288 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,250,000Aug 2025 | $12,6042025 | Amount on Record Mar 2018 | 2 Names on Record | Assessor + 2 DocumentsUpdated May 2026 |
3 bd · 2.5 ba · 2,394 sqft · built 2002 · 0.192 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $8,6822025 | 2 Names on Record Owner Occupied | Assessor + 1 DocumentUpdated May 2026 |
5 bd · 5.75 ba · 4,754 sqft · built 2023 · 0.288 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $775,000Nov 2021 | $30,2892025 | Amount on Record Sep 2021 | 2 Names on Record Owner Occupied | Assessor + 3 DocumentsUpdated Jul 2026 |
4 bd · 4.5 ba · 2,936 sqft · built 2021 · 0.192 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,385,000Apr 2021 | $26,2172025 | Amount on Record Dec 2019 | 1 Name on Record Owner Occupied | Assessor + 3 DocumentsUpdated Jul 2026 |
2 bd · 2 ba · 1,815 sqft · built 1980 · 0.192 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $3,2602025 | 2 Names on Record Owner Occupied | Assessor + 2 DocumentsUpdated May 2026 |
4 bd · 2.5 ba · 2,459 sqft · built 2003 · 0.192 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $705,000Jul 2017 | $11,5412025 | Amount on Record Jul 2008 | 2 Names on Record Owner Occupied | Assessor + 2 DocumentsUpdated May 2026 |
4 bd · 3.5 ba · 2,888 sqft · built 2017 · 0.192 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,800,000Apr 2024 | $27,1652025 | Amount on Record Apr 2017 | 1 Name on Record | Assessor + 2 DocumentsUpdated 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 11% of the US · above 5% of Florida |
|---|---|
| Wildfire Likelihood | About 1 in 5,263 per year |
| Exposure | Direct 1 of 2 cells directly exposed · 2 adjoin burnable vegetation |