Orange County property records for 20 addresses on Cutter Sail Pl, Winter Garden, FL · Last verified October 2026
| Properties | 20 |
|---|---|
| Median Sale Price | $842,110 |
| Deeds and Mortgages on File | 35 |
| Median Price per Sqft | $264 |
| Owner Occupied | 75% |
| Median Annual Tax Bill | $12,282 |
| Median Year Built | 2021 |
| Median Ownership Tenure | 4 years |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
15706 Cutter Sail Pl |
5 bd · 4.5 ba · 3,523 sqft built 2020 · 0.187 acres | $1,000,000 Mar 2026 | $11,263 2025 | Assessor + 3 Documents Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
15707 Cutter Sail Pl |
3 bd · 3 ba · 2,285 sqft built 2020 · 0.208 acres | $789,900 Jun 2025 | $7,855 2025 | Assessor + 1 Document Updated Jul 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
15712 Cutter Sail Pl |
6 bd · 4 ba · 3,775 sqft built 2022 · 0.152 acres | $1,069,995 Jun 2022 | $15,463 2025 | Assessor + 1 Document Updated Aug 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
15713 Cutter Sail Pl |
5 bd · 5.5 ba · 4,061 sqft built 2021 · 0.152 acres | $939,045 Mar 2021 | $14,503 2025 | Assessor + 2 Documents Updated May 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
15718 Cutter Sail Pl |
5 bd · 4.5 ba · 3,755 sqft built 2021 · 0.152 acres | $893,945 Oct 2021 | $14,968 2025 | Assessor + 1 Document Updated May 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
15719 Cutter Sail Pl |
4 bd · 3.5 ba · 2,477 sqft built 2020 · 0.152 acres | $548,185 Feb 2021 | $10,702 2025 | Assessor + 2 Documents Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
15724 Cutter Sail Pl |
5 bd · 4.5 ba · 3,510 sqft built 2022 · 0.152 acres | $1,000,000 Jan 2026 | $16,339 2025 | Assessor + 3 Documents Updated Jun 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
15725 Cutter Sail Pl |
3 bd · 3 ba · 2,306 sqft built 2021 · 0.152 acres | $695,000 Feb 2024 | $10,790 2025 | Assessor + 2 Documents Updated May 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
15730 Cutter Sail Pl |
5 bd · 4.5 ba · 3,703 sqft built 2020 · 0.166 acres | $1,180,000 Jan 2025 | $11,989 2025 | Assessor + 3 Documents Updated Aug 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
15731 Cutter Sail Pl |
4 bd · 4 ba · 2,538 sqft built 2021 · 0.175 acres | $612,745 Sep 2021 | $11,767 2025 | Assessor + 1 Document Updated Aug 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
15736 Cutter Sail Pl |
5 bd · 4.5 ba · 4,044 sqft built 2020 · 0.166 acres | $1,070,000 Oct 2022 | $15,348 2025 | Assessor + 4 Documents Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
15737 Cutter Sail Pl |
5 bd · 4.5 ba · 4,005 sqft built 2021 · 0.175 acres | $842,110 Jul 2021 | $12,387 2025 | Assessor + 1 Document Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
15742 Cutter Sail Pl |
5 bd · 5 ba · 3,601 sqft built 2021 · 0.152 acres | $836,636 May 2021 | $13,476 2025 | Assessor + 2 Documents Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
15743 Cutter Sail Pl |
4 bd · 3.5 ba · 2,857 sqft built 2022 · 0.152 acres | $655,790 Feb 2022 | $10,486 2025 | Assessor + 2 Documents Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
15748 Cutter Sail Pl |
5 bd · 3.5 ba · 3,514 sqft built 2022 · 0.152 acres | $1,054,894 Mar 2022 | $12,976 2025 | Assessor Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
15749 Cutter Sail Pl |
3 bd · 2 ba · 2,285 sqft built 2019 · 0.152 acres | $710,000 Jun 2024 | $9,928 2025 | Assessor + 1 Document Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
15754 Cutter Sail Pl |
5 bd · 4.5 ba · 3,959 sqft built 2020 · 0.152 acres | $670,380 Dec 2020 | $15,053 2025 | Assessor + 1 Document Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
15755 Cutter Sail Pl |
4 bd · 3.5 ba · 2,829 sqft built 2020 · 0.152 acres | $870,000 Nov 2023 | $12,282 2025 | Assessor + 2 Documents Updated May 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
15760 Cutter Sail Pl |
5 bd · 4.5 ba · 3,510 sqft built 2020 · 0.195 acres | $673,735 Jul 2020 | $11,160 2025 | Assessor + 3 Documents Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
15761 Cutter Sail Pl |
5 bd · 4.5 ba · 3,734 sqft built 2021 · 0.199 acres | $596,965 Jun 2021 | $9,246 2025 | Assessor Updated May 2026 | 2 Owners on File Owner Occupied |