Orange County property records for 17 addresses on Hollywood Ave, Winter Park, FL · Last verified October 2026
| Properties | 17 |
|---|---|
| Median Sale Price | $850,000 |
| Deeds and Mortgages on File | 15 |
| Median Price per Sqft | $480 |
| Owner Occupied | 59% |
| Median Annual Tax Bill | $7,032 |
| Median Year Built | 1959 |
| Median Ownership Tenure | 5 years |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1717 Hollywood Ave |
4 bd · 2.5 ba · 3,153 sqft built 2006 · 0.257 acres | $1,160,000 May 2024 | $23,072 2025 | Assessor + 1 Document Updated Oct 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1745 Hollywood Ave |
4 bd · 3.5 ba · 3,661 sqft built 1952 · 0.285 acres | $850,000 Jan 2021 | $13,785 2025 | Assessor + 2 Documents Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1755 Hollywood Ave |
3 bd · 2 ba · 1,630 sqft built 1977 · 0.142 acres | $312,500 Oct 2016 | $9,283 2025 | Assessor Updated May 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1756 Hollywood Ave |
3 bd · 2 ba · 1,838 sqft built 1922 · 0.368 acres | $1,000,000 May 2023 | $7,032 2025 | Assessor + 4 Documents Updated Oct 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1760 Hollywood Ave |
4 bd · 2 ba · 1,918 sqft built 1988 · 0.251 acres | $3,422 2025 | Assessor Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1765 Hollywood Ave |
4 bd · 3.5 ba · 2,289 sqft built 1977 · 0.142 acres | $326,000 Sep 2012 | $5,876 2025 | Assessor + 1 Document Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1770 Hollywood Ave |
4 bd · 2 ba · 1,572 sqft built 1924 · 0.334 acres | $2,584 2025 | Assessor + 1 Document Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1775 Hollywood Ave |
3 bd · 2 ba · 1,587 sqft built 1977 · 0.142 acres | $554,000 Aug 2024 | $8,666 2025 | Assessor Updated Oct 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1785 Hollywood Ave |
3 bd · 2 ba · 1,532 sqft built 1977 · 0.149 acres | $1,168,000 Sep 2025 | $5,565 2025 | Assessor + 3 Documents Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1790 Hollywood Ave |
2 bd · 2 ba · 1,406 sqft built 1925 · 0.167 acres | $680,000 Mar 2023 | $8,806 2025 | Assessor + 2 Documents Updated Oct 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1800 Hollywood Ave |
3 bd · 2 ba · 1,592 sqft built 1930 · 0.334 acres | $2,750 2025 | Assessor Updated May 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1810 Hollywood Ave |
3 bd · 1 ba · 1,040 sqft built 1959 · 0.174 acres | $500,000 Jan 2025 | $7,219 2025 | Assessor Updated May 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1819 Hollywood Ave |
3 bd · 2 ba · 1,490 sqft built 1986 · 0.142 acres | $208,600 Mar 2003 | $4,210 2025 | Assessor Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1820 Hollywood Ave |
3 bd · 1.5 ba · 1,260 sqft built 1958 · 0.2 acres | $275,000 Feb 2005 | $2,788 2025 | Assessor + 1 Document Updated May 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1840 Hollywood Ave |
3 bd · 1.5 ba · 1,040 sqft built 1958 · 0.2 acres | $200,000 Dec 2014 | $3,216 2025 | Assessor Updated May 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1850 Hollywood Ave |
1,507 sqft built 1958 · 0.214 acres | $225,000 Aug 2001 | $9,752 2025 | Assessor Updated May 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1855 Hollywood Ave |
6,960 sqft built 1980 · 0.572 acres | $22,412 2025 | Assessor Updated May 2026 | Owner on File |