Orange County property records for 59 addresses on Bolero Rd, Winter Garden, FL · Last verified October 2026
| Properties | 59 |
|---|---|
| Median Sale Price | $579,556 |
| Deeds and Mortgages on File | 81 |
| Median Price per Sqft | $203 |
| Owner Occupied | 78% |
| Median Annual Tax Bill | $9,700 |
| Median Year Built | 2020 |
| Median Ownership Tenure | 5 years |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9296 Bolero Rd |
4 bd · 3 ba · 2,117 sqft built 2020 · 0.171 acres | $687,000 Jan 2025 | $9,794 2025 | Assessor + 1 Document Updated Jul 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9302 Bolero Rd |
4 bd · 3.5 ba · 3,115 sqft built 2021 · 0.137 acres | $509,876 May 2021 | $9,579 2025 | Assessor + 1 Document Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9308 Bolero Rd |
5 bd · 4.5 ba · 2,953 sqft built 2021 · 0.137 acres | $511,495 Mar 2021 | $12,125 2025 | Assessor + 1 Document Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9314 Bolero Rd |
4 bd · 3 ba · 2,117 sqft built 2020 · 0.137 acres | $469,435 Jan 2021 | $7,729 2025 | Assessor + 1 Document Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9320 Bolero Rd |
3 bd · 3 ba · 2,040 sqft built 2020 · 0.137 acres | $471,263 Mar 2021 | $7,446 2025 | Assessor + 1 Document Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9326 Bolero Rd |
4 bd · 3.5 ba · 3,115 sqft built 2020 · 0.137 acres | $1,065,000 Jul 2023 | $10,531 2025 | Assessor + 1 Document Updated May 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9332 Bolero Rd |
4 bd · 3 ba · 2,117 sqft built 2020 · 0.137 acres | $466,203 Dec 2020 | $4,864 2025 | Assessor + 2 Documents Updated Jun 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9338 Bolero Rd |
4 bd · 3 ba · 2,687 sqft built 2021 · 0.137 acres | $520,656 Jan 2021 | $8,685 2025 | Assessor + 1 Document Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9344 Bolero Rd |
5 bd · 4 ba · 2,594 sqft built 2020 · 0.137 acres | $489,100 Jan 2021 | $8,424 2025 | Assessor + 1 Document Updated May 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9350 Bolero Rd |
4 bd · 3 ba · 3,066 sqft built 2020 · 0.137 acres | $510,335 Dec 2020 | $11,290 2025 | Assessor + 1 Document Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9356 Bolero Rd |
4 bd · 3 ba · 2,117 sqft built 2020 · 0.137 acres | $454,835 Nov 2020 | $7,981 2025 | Assessor + 1 Document Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9362 Bolero Rd |
4 bd · 3 ba · 2,181 sqft built 2020 · 0.165 acres | $473,351 Dec 2020 | $6,831 2025 | Assessor + 1 Document Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9368 Bolero Rd |
4 bd · 3.5 ba · 3,066 sqft built 2021 · 0.165 acres | $604,845 Feb 2021 | $12,882 2025 | Assessor + 2 Documents Updated May 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9374 Bolero Rd |
5 bd · 4 ba · 2,594 sqft built 2020 · 0.137 acres | $687,000 Feb 2026 | $7,207 2025 | Assessor + 3 Documents Updated Jul 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9380 Bolero Rd |
5 bd · 4.5 ba · 2,953 sqft built 2021 · 0.137 acres | $1,340,000 Dec 2024 | $13,989 2025 | Assessor + 1 Document Updated Sep 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9386 Bolero Rd |
4 bd · 3.5 ba · 3,115 sqft built 2020 · 0.139 acres | $554,230 Oct 2020 | $12,150 2025 | Assessor + 2 Documents Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9402 Bolero Rd |
1.87 acres | $1 2025 | Assessor + 1 Document Updated May 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9406 Bolero Rd |
4 bd · 3.5 ba · 2,953 sqft built 2020 · 0.138 acres | $795,000 Nov 2025 | $7,750 2025 | Assessor + 2 Documents Updated Jul 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9412 Bolero Rd |
4 bd · 3 ba · 2,687 sqft built 2020 · 0.138 acres | $443,740 Jun 2020 | $10,306 2025 | Assessor + 1 Document Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9418 Bolero Rd |
4 bd · 3 ba · 2,117 sqft built 2020 · 0.138 acres | $690,000 Sep 2023 | $9,805 2025 | Assessor + 1 Document Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9424 Bolero Rd |
4 bd · 3.5 ba · 3,066 sqft built 2020 · 0.138 acres | $493,925 Feb 2020 | $9,348 2025 | Assessor Updated May 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9430 Bolero Rd |
4 bd · 3 ba · 2,117 sqft built 2019 · 0.151 acres | $442,300 Dec 2019 | $6,605 2025 | Assessor + 2 Documents Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9433 Bolero Rd |
0.154 acres | $24,000 May 1994 | $1 2025 | Assessor + 1 Document Updated Sep 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9436 Bolero Rd |
4 bd · 3.5 ba · 2,594 sqft built 2020 · 0.178 acres | $493,925 May 2020 | $614 2025 | Assessor + 2 Documents Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9442 Bolero Rd |
4 bd · 3.5 ba · 3,066 sqft built 2020 · 0.138 acres | $512,483 May 2020 | $6,970 2025 | Assessor + 2 Documents Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9448 Bolero Rd |
4 bd · 2.5 ba · 2,117 sqft built 2020 · 0.138 acres | $430,888 Jan 2020 | $6,347 2025 | Assessor + 1 Document Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9454 Bolero Rd |
4 bd · 3 ba · 2,687 sqft built 2020 · 0.138 acres | $466,317 Aug 2020 | $10,438 2025 | Assessor + 1 Document Updated May 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9460 Bolero Rd |
4 bd · 3.5 ba · 3,066 sqft built 2020 · 0.152 acres | $477,645 Apr 2020 | $5,882 2025 | Assessor + 1 Document Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9461 Bolero Rd |
0.131 acres | $1 2025 | Assessor + 1 Document Updated May 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9466 Bolero Rd |
5 bd · 4.5 ba · 2,953 sqft built 2020 · 0.219 acres | $955,000 Aug 2024 | $12,758 2025 | Assessor + 2 Documents Updated Sep 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9470 Bolero Rd |
4 bd · 3.5 ba · 3,066 sqft built 2020 · 0.138 acres | $479,025 Apr 2020 | $11,630 2025 | Assessor + 1 Document Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9476 Bolero Rd |
4 bd · 3 ba · 2,117 sqft built 2020 · 0.138 acres | $419,165 Jun 2020 | $6,347 2025 | Assessor + 1 Document Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9482 Bolero Rd |
4 bd · 3.5 ba · 3,115 sqft built 2020 · 0.228 acres | $900,000 Jan 2025 | $7,910 2025 | Assessor + 1 Document Updated Oct 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9488 Bolero Rd |
4 bd · 3 ba · 2,117 sqft built 2020 · 0.183 acres | $428,000 Aug 2020 | $6,342 2025 | Assessor + 2 Documents Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9506 Bolero Rd |
4 bd · 3 ba · 2,117 sqft built 2020 · 0.148 acres | $735,000 Aug 2026 | $6,938 2025 | Assessor + 2 Documents Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9512 Bolero Rd |
4 bd · 3.5 ba · 3,066 sqft built 2020 · 0.149 acres | $508,625 Jun 2020 | $9,889 2025 | Assessor + 1 Document Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9518 Bolero Rd |
5 bd · 4 ba · 2,594 sqft built 2020 · 0.149 acres | $463,396 Jul 2020 | $8,587 2025 | Assessor + 1 Document Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9524 Bolero Rd |
4 bd · 3 ba · 2,117 sqft built 2020 · 0.149 acres | $720,000 Dec 2023 | $10,408 2025 | Assessor + 2 Documents Updated Jul 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9530 Bolero Rd |
4 bd · 3.5 ba · 3,066 sqft built 2020 · 0.186 acres | $535,805 Jun 2020 | $8,459 2025 | Assessor + 1 Document Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9536 Bolero Rd |
4 bd · 3.5 ba · 2,594 sqft built 2020 · 0.186 acres | $705,404 Oct 2021 | $12,218 2025 | Assessor + 2 Documents Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9542 Bolero Rd |
5 bd · 2.5 ba · 2,953 sqft built 2020 · 0.149 acres | $495,000 Apr 2020 | $11,123 2025 | Assessor + 1 Document Updated May 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9543 Bolero Rd |
4 bd · 3.5 ba · 2,950 sqft built 2020 · 0.333 acres | $599,998 Jan 2021 | $9,761 2025 | Assessor + 1 Document Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9548 Bolero Rd |
5 bd · 3.5 ba · 3,634 sqft built 2021 · 0.179 acres | $598,366 Jan 2021 | $10,172 2025 | Assessor + 2 Documents Updated May 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9549 Bolero Rd |
5 bd · 3.5 ba · 3,620 sqft built 2021 · 0.286 acres | $975,000 Jul 2026 | $14,109 2025 | Assessor + 2 Documents Updated Oct 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9554 Bolero Rd |
4 bd · 3.5 ba · 2,701 sqft built 2021 · 0.179 acres | $865,000 Jun 2025 | $10,110 2025 | Assessor + 1 Document Updated Jul 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9555 Bolero Rd |
4 bd · 4.5 ba · 3,123 sqft built 2021 · 0.255 acres | $1,265,000 Jul 2024 | $14,568 2025 | Assessor + 1 Document Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9560 Bolero Rd |
5 bd · 4.5 ba · 3,123 sqft built 2021 · 0.197 acres | $593,057 May 2021 | $9,700 2025 | Assessor + 1 Document Updated May 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9561 Bolero Rd |
4 bd · 3.5 ba · 2,705 sqft built 2021 · 0.211 acres | $805,000 Oct 2022 | $11,924 2025 | Assessor + 3 Documents Updated May 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9566 Bolero Rd |
5 bd · 3.5 ba · 3,620 sqft built 2021 · 0.182 acres | $625,681 Jun 2021 | $14,421 2025 | Assessor + 2 Documents Updated Oct 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9567 Bolero Rd |
5 bd · 3.5 ba · 3,620 sqft built 2021 · 0.181 acres | $100 Apr 2021 | $14,179 2025 | Assessor + 2 Documents Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9572 Bolero Rd |
3 bd · 2.5 ba · 2,348 sqft built 2020 · 0.257 acres | $499,465 Jan 2021 | $6,928 2025 | Assessor + 3 Documents Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9573 Bolero Rd |
4 bd · 4.5 ba · 3,099 sqft built 2021 · 0.2 acres | $635,005 Mar 2021 | $10,657 2025 | Assessor + 1 Document Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9578 Bolero Rd |
5 bd · 3.5 ba · 3,634 sqft built 2021 · 0.224 acres | $600,325 Apr 2021 | $13,090 2025 | Assessor + 2 Documents Updated May 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9579 Bolero Rd |
4 bd · 3.5 ba · 2,758 sqft built 2021 · 0.233 acres | $637,391 Apr 2021 | $9,477 2025 | Assessor + 1 Document Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9584 Bolero Rd |
4 bd · 3.5 ba · 2,705 sqft built 2021 · 0.274 acres | $605,136 Jun 2021 | $9,418 2025 | Assessor + 1 Document Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9585 Bolero Rd |
5 bd · 3.5 ba · 3,620 sqft built 2021 · 0.311 acres | $739,196 Feb 2021 | $11,910 2025 | Assessor + 1 Document Updated May 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9590 Bolero Rd |
5 bd · 3.5 ba · 3,620 sqft built 2021 · 0.328 acres | $631,613 Mar 2021 | $11,400 2025 | Assessor + 1 Document Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9591 Bolero Rd |
4 bd · 4.5 ba · 3,123 sqft built 2021 · 0.315 acres | $1,240,000 May 2024 | $13,917 2025 | Assessor + 1 Document Updated May 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9597 Bolero Rd |
4 bd · 3.5 ba · 2,758 sqft built 2021 · 0.307 acres | $579,556 Feb 2021 | $8,869 2025 | Assessor + 1 Document Updated May 2026 | 2 Owners on File Owner Occupied |