Gilbert Road, Winter Park, FL
Everything we know about Gilbert Road in Winter Park: 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.
28 homes sit on Gilbert Road in Winter Park, FL (ZIP 32792), built 1964–1968, a typical 1,868 sq ft with 4 bedrooms. 3 are for sale right now from $649,000 to $710,000. Homes that sold since 2023 went for a median $650,000.
For sale on Gilbert Road now
The homes on Gilbert Road
28 single-family. Built by decade: 1960s 28.
Last recorded sales (parcel record)
| Address | Sold | Date | Built | Sq ft |
|---|---|---|---|---|
| 417 Gilbert Road | $650,000 | 2025-01-21 | 1964 | 2,231 |
| 305 Gilbert Road | $650,000 | 2024-09-04 | 1964 | 2,031 |
| 754 Gilbert Road | $670,000 | 2024-08-16 | 1968 | 2,289 |
| 313 Gilbert Road | $650,000 | 2024-05-24 | 1964 | 1,642 |
| 753 Gilbert Road | $680,000 | 2024-04-19 | 1968 | 2,328 |
| 418 Gilbert Road | $690,000 | 2023-11-10 | 1964 | 1,680 |
| 627 Gilbert Road | $584,999 | 2023-08-07 | 1966 | 2,148 |
| 643 Gilbert Road | $483,500 | 2023-06-28 | 1966 | 2,185 |
| 543 Gilbert Road | $530,000 | 2022-04-21 | 1965 | 1,981 |
| 502 Gilbert Road | $590,000 | 2022-02-22 | 1965 | 1,854 |
| 426 Gilbert Road | $440,000 | 2021-09-30 | 1964 | 1,658 |
| 551 Gilbert Road | $395,000 | 2021-06-22 | 1965 | 1,900 |
| 345 Gilbert Road | $298,000 | 2019-07-23 | 1964 | 1,692 |
| 337 Gilbert Road | $325,000 | 2017-08-04 | 1964 | 1,715 |
| 730 Gilbert Road | $395,000 | 2017-03-24 | 1967 | 1,818 |
| 619 Gilbert Road | $465,000 | 2016-04-11 | 1966 | 2,595 |
| 510 Gilbert Road | $300,000 | 2015-08-12 | 1965 | 1,668 |
| 745 Gilbert Road | $255,000 | 2015-01-23 | 1968 | 2,047 |
| 433 Gilbert Road | $255,000 | 2014-08-01 | 1965 | 1,770 |
| 518 Gilbert Road | $239,950 | 2014-07-09 | 1965 | 1,573 |
Communities along Gilbert Road
- winter park pines · 11 homes on the street
- winter park pines · 4 homes on the street
- winter park pines · 4 homes on the street
- winter park pines · 2 homes on the street
- winter park pines · 1 homes on the street
- winter park pines · 1 homes on the street
- winter park pines · 1 homes on the street
- winter park pines · 1 homes on the street
- winter park pines · 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 350 homes for sale in Winter Park, homes for sale in 32792.