Windward Drive, Osprey, FL
Everything we know about Windward Drive in Osprey: 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.
26 homes sit on Windward Drive in Osprey, FL (ZIP 34229), built 1978–2003, a typical 2,495 sq ft with 3 bedrooms. 1 is for sale right now from $1,047,000. 3 closed in the last 12 months at a median of $565,000. Homes that sold since 2023 went for a median $782,500.
For sale on Windward Drive now
Recent sales on Windward Drive
| Address | Sold | Closed | Beds / baths | Sq ft |
|---|---|---|---|---|
| 204 Windward Drive | $800,000 | 2026-08-24 | 3 / 3.0 | 2,486 |
| 186 Windward Drive | $565,000 | 2026-07-20 | 3 / 2.0 | 2,505 |
| 102 Windward Drive | $565,000 | 2026-06-04 | 3 / 2.5 | 2,134 |
The homes on Windward Drive
26 single-family. Built by decade: 1970s 4, 1980s 18, 1990s 2, 2000s 2.
Last recorded sales (parcel record)
| Address | Sold | Date | Built | Sq ft |
|---|---|---|---|---|
| 204 Windward Drive | $800,000 | 2026-08-24 | 1986 | 2,486 |
| 186 Windward Drive | $565,000 | 2026-07-20 | 1983 | 2,505 |
| 102 Windward Drive | $565,000 | 2026-06-04 | 1986 | 2,134 |
| 1212 Windward Drive | $645,000 | 2025-08-25 | 1982 | 1,994 |
| 1251 Windward Drive | $875,000 | 2024-09-03 | 1986 | 2,015 |
| 216 Windward Drive | $782,500 | 2023-11-20 | 1982 | 2,575 |
| 228 Windward Drive | $1,200,000 | 2023-05-25 | 1981 | 2,850 |
| 1275 Windward Drive | $552,800 | 2019-10-29 | 1984 | 2,059 |
| 1263 Windward Drive | $475,000 | 2019-08-30 | 1985 | 2,058 |
| 138 Windward Drive | $402,000 | 2018-11-27 | 1985 | 2,204 |
| 173 Windward Drive | $515,000 | 2018-07-16 | 1978 | 3,118 |
| 217 Windward Drive | $635,000 | 2018-01-31 | 1985 | 2,552 |
| 185 Windward Drive | $635,000 | 2017-12-15 | 1979 | 2,396 |
| 1305 Windward Drive | $525,000 | 2017-01-10 | 1997 | 2,748 |
| 174 Windward Drive | $350,000 | 2016-01-29 | 1986 | 2,791 |
| 1260 Windward Drive | $537,500 | 2015-05-15 | 1983 | 2,824 |
| 135 Windward Drive | $440,000 | 2015-04-29 | 1986 | 2,415 |
| 306 Windward Drive | $300,000 | 2015-02-17 | 1980 | 1,963 |
| 126 Windward Drive | $320,000 | 2014-03-24 | 1981 | 1,876 |
| 147 Windward Drive | $400,000 | 2014-03-18 | 1978 | 2,154 |
Communities along Windward Drive
- Southbay Yacht & Racquet Club · 19 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 85 homes for sale in Osprey, homes for sale in 34229.