Bolero Road, Winter Garden, FL
Everything we know about Bolero Road in Winter Garden: what is for sale, what has sold, what the homes are like and which communities the street runs through — from the MLS record and county parcel data, refreshed nightly.
32 homes sit on Bolero Road in Winter Garden, FL (ZIP 34787), built 2020–2021, a typical 2,924 sq ft with 4 bedrooms. Nothing is listed for sale on the street today. Homes that sold since 2023 went for a median $882,500.
The homes on Bolero Road
31 single-family, 1 condo/townhome/other. Built by decade: 2020s 32.
Last recorded sales (parcel record)
| Address | Sold | Date | Built | Sq ft |
|---|---|---|---|---|
| 9506 Bolero Road | $735,000 | 2026-07-31 | 2020 | 2,117 |
| 9549 Bolero Road | $975,000 | 2026-07-01 | 2021 | 3,910 |
| 9374 Bolero Road | $687,000 | 2026-01-28 | 2020 | 2,840 |
| 9406 Bolero Road | $795,000 | 2025-11-05 | 2020 | 3,299 |
| 9554 Bolero Road | $865,000 | 2025-06-05 | 2021 | 2,916 |
| 9482 Bolero Road | $900,000 | 2025-01-23 | 2020 | 3,316 |
| 9466 Bolero Road | $955,000 | 2024-08-27 | 2020 | 3,227 |
| 9555 Bolero Road | $1,265,000 | 2024-07-12 | 2021 | 3,416 |
| 9591 Bolero Road | $1,240,000 | 2024-04-25 | 2021 | 3,416 |
| 9524 Bolero Road | $720,000 | 2023-12-14 | 2020 | 2,117 |
| 9418 Bolero Road | $690,000 | 2023-09-22 | 2020 | 2,117 |
| 9326 Bolero Road | $1,065,000 | 2023-06-07 | 2020 | 3,334 |
| 9561 Bolero Road | $805,000 | 2022-10-17 | 2021 | 2,921 |
| 9536 Bolero Road | $705,404 | 2021-10-22 | 2020 | 2,840 |
| 9560 Bolero Road | $593,057 | 2021-05-19 | 2020 | 3,408 |
| 9579 Bolero Road | $637,391 | 2021-04-09 | 2021 | 2,769 |
| 9320 Bolero Road | $471,263 | 2021-04-08 | 2021 | 2,040 |
| 9590 Bolero Road | $631,613 | 2021-03-25 | 2020 | 3,911 |
| 9567 Bolero Road | $691,000 | 2021-03-15 | 2021 | 3,700 |
| 9308 Bolero Road | $511,495 | 2021-02-26 | 2020 | 3,227 |
Communities along Bolero Road
- Waterleigh · 13 homes on the street
- Waterleigh · 11 homes on the street
- Waterleigh · 2 homes on the street
- Waterleigh · 1 homes on the street
- Waterleigh · 1 homes on the street
How to read this
Home counts, build years, sizes and last sales come from the county parcel record joined to MLS history; listings and 12-month closings from the live MLS feeds as of October 14, 2026. Listings appear courtesy of the listing brokerage under IDX rules; information deemed reliable but not guaranteed. See also all 710 homes for sale in Winter Garden, homes for sale in 34787.