Orange County property records for 8 addresses on Gay Rd, Winter Park, FL · Last verified October 2026
| Properties | 99 |
|---|---|
| Median Sale Price | $231,000 |
| Deeds and Mortgages on File | 94 |
| Median Price per Sqft | $229 |
| Owner Occupied | 56% |
| Median Annual Tax Bill | $2,630 |
| Median Year Built | 1972 |
| Median Ownership Tenure | 8 years |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1408 Gay Rd |
5,737 sqft built 2005 · 0.252 acres | $2,129,700 Jul 2016 | $40,319 2025 | Assessor + 1 Document Updated Sep 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1414 Gay Rd |
3,048 sqft built 1950 · 0.202 acres | $917,000 Nov 2024 | $11,317 2025 | Assessor + 2 Documents Updated Oct 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1420 Gay Rd |
2 bd · 2 ba · 1,267 sqft built 1952 · 0.202 acres | $835,000 Nov 2025 | $7,265 2025 | Assessor + 1 Document Updated Oct 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1424 Gay Rd |
572 sqft built 1960 · 0.202 acres | $1,600,000 Aug 2019 | $6,565 2025 | Assessor + 2 Documents Updated Oct 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1428 Gay Rd |
0.204 acres | $1,600,000 Aug 2019 | $6,028 2025 | Assessor + 2 Documents Updated Oct 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1500 Gay Rd |
5.55 acres | $19,300 Apr 2003 | $148 2025 | Assessor Updated May 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1500 Gay Rd |
92 units · 732 sq ft Built 1972 | $230,000 Sep 2026 | $2,630 2025 |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1550 Gay Rd |
2 bd · 1 ba · 127,737 sqft built 1972 · 3.2 acres | $1,401,900 Jan 2007 | $6,710 2025 | Assessor Updated May 2026 | Owner on File |