Winding Oak Lane, Longwood, FL
Everything we know about Winding Oak Lane in Longwood: 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.
33 homes sit on Winding Oak Lane in Longwood, FL (ZIP 32750), built 1990–1994, a typical 1,142 sq ft with 3 bedrooms. Nothing is listed for sale on the street today. Homes that sold since 2023 went for a median $315,000.
The homes on Winding Oak Lane
29 single-family, 4 condo/townhome/other. Built by decade: 1990s 33.
Last recorded sales (parcel record)
| Address | Sold | Date | Built | Sq ft |
|---|---|---|---|---|
| 528 Winding Oak Ln | $319,000 | 2025-09-26 | 1994 | 1,142 |
| 428 Winding Oak Lane | $315,000 | 2025-04-29 | 1993 | 1,142 |
| 496 Winding Oak Lane | $307,500 | 2024-08-23 | 1993 | 1,107 |
| 533 Winding Oak Lane | $325,000 | 2022-10-16 | 1992 | 1,142 |
| 405 Winding Oak Lane | $200,000 | 2022-08-30 | 1990 | 1,344 |
| 513 Winding Oak Lane | $320,000 | 2022-05-12 | 1992 | 1,107 |
| 456 Winding Oak Lane | $260,000 | 2022-03-10 | 1993 | 1,076 |
| 552 Winding Oak Lane | $247,500 | 2021-06-21 | 1993 | 1,396 |
| 437 Winding Oak Lane | $247,000 | 2021-04-15 | 1992 | 1,144 |
| 441 Winding Oak Lane | $223,000 | 2021-03-04 | 1993 | 1,144 |
| 444 Winding Oak Lane | $235,000 | 2021-02-17 | 1993 | 1,144 |
| 544 Winding Oak Lane | $205,000 | 2020-09-17 | 1994 | 1,142 |
| 532 Winding Oak Lane | $200,000 | 2020-07-15 | 1993 | 1,144 |
| 420 Winding Oak Lane | $129,500 | 2020-02-11 | 1990 | 1,512 |
| 425 Winding Oak Lane | $88,000 | 2018-12-14 | 1990 | 1,043 |
| 424 Winding Oak Lane | $170,000 | 2018-11-30 | 1993 | 1,142 |
| 520 Winding Oak Lane | $155,000 | 2018-04-09 | 1993 | 1,142 |
| 500 Winding Oak Lane | $167,500 | 2018-03-30 | 1992 | 1,144 |
| 433 Winding Oak Lane | $160,000 | 2018-03-16 | 1992 | 1,396 |
| 440 Winding Oak Lane | $147,979 | 2018-03-16 | 1992 | 973 |
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 15, 2026. Listings appear courtesy of the listing brokerage under IDX rules; information deemed reliable but not guaranteed. See also all 224 homes for sale in Longwood, homes for sale in 32750.