Winding Oaks Drive, Orlando, FL
Everything we know about Winding Oaks Drive in Orlando: 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.
42 homes sit on Winding Oaks Drive in Orlando, FL (ZIP 32825), built 2001–2003, a typical 3,034 sq ft with 4 bedrooms. Nothing is listed for sale on the street today. 1 closed in the last 12 months at a median of $675,000. Homes that sold since 2023 went for a median $620,000.
Recent sales on Winding Oaks Drive
| Address | Sold | Closed | Beds / baths | Sq ft |
|---|---|---|---|---|
| 1815 Winding Oaks Drive | $675,000 | 2026-04-17 | 4 / 3.0 | 2,717 |
The homes on Winding Oaks Drive
42 single-family. Built by decade: 2000s 42.
Last recorded sales (parcel record)
| Address | Sold | Date | Built | Sq ft |
|---|---|---|---|---|
| 1815 Winding Oaks Drive | $675,000 | 2026-04-17 | 2003 | 2,717 |
| 1919 Winding Oaks Drive | $650,000 | 2025-10-07 | 2002 | 2,556 |
| 2038 Winding Oaks Drive | $590,000 | 2025-02-11 | 2003 | 2,580 |
| 1839 Winding Oaks Drive | $585,000 | 2023-04-18 | 2003 | 3,152 |
| 1713 Winding Oaks Drive | $451,000 | 2021-07-21 | 2003 | 2,926 |
| 2014 Winding Oaks Drive | $510,000 | 2021-07-02 | 2003 | 2,559 |
| 2020 Winding Oaks Drive | $465,000 | 2021-02-01 | 2003 | 3,257 |
| 1736 Winding Oaks Drive | $425,000 | 2020-09-18 | 2003 | 3,326 |
| 1913 Winding Oaks Drive | $450,000 | 2020-09-17 | 2003 | 2,717 |
| 1701 Winding Oaks Drive | $395,000 | 2019-12-30 | 2003 | 3,334 |
| 1707 Winding Oaks Drive | $425,000 | 2019-09-20 | 2003 | 3,079 |
| 1832 Winding Oaks Drive | $425,000 | 2019-06-21 | 2002 | 3,034 |
| 1850 Winding Oaks Drive | $440,000 | 2019-05-22 | 2002 | 3,222 |
| 1942 Winding Oaks Drive | $450,000 | 2018-10-03 | 2002 | 3,240 |
| 1737 Winding Oaks Drive | $405,000 | 2018-09-07 | 2002 | 3,257 |
| 1725 Winding Oaks Drive | $346,000 | 2018-07-30 | 2003 | 2,553 |
| 1918 Winding Oaks Drive | $367,000 | 2018-05-25 | 2003 | 2,620 |
| 1930 Winding Oaks Drive | $405,000 | 2018-02-08 | 2003 | 3,280 |
| 1905 Winding Oaks Drive | $326,000 | 2018-01-19 | 2003 | 2,717 |
| 1731 Winding Oaks Drive | $323,000 | 2017-10-03 | 2002 | 2,686 |
Communities along Winding Oaks Drive
- Villages Rio Pinar · 22 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 4,155 homes for sale in Orlando, homes for sale in 32825.