Okaloosa Drive, Winter Haven, FL
Everything we know about Okaloosa Drive in Winter Haven: 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 Okaloosa Drive in Winter Haven, FL (ZIP 33884), built 1961–1988, a typical 1,740 sq ft with 3 bedrooms. Nothing is listed for sale on the street today. Homes that sold since 2023 went for a median $300,000.
The homes on Okaloosa Drive
32 single-family. Built by decade: 1960s 5, 1970s 23, 1980s 4.
Last recorded sales (parcel record)
| Address | Sold | Date | Built | Sq ft |
|---|---|---|---|---|
| 237 Okaloosa Drive | $300,000 | 2026-06-18 | 1964 | 1,573 |
| 329 Okaloosa Drive | $280,000 | 2026-05-04 | 1972 | 1,900 |
| 222 Okaloosa Drive | $270,000 | 2025-10-08 | 1988 | 1,835 |
| 149 Okaloosa Drive | $398,000 | 2025-04-11 | 1974 | 2,581 |
| 324 Okaloosa Drive | $499,000 | 2024-06-11 | 1978 | 3,351 |
| 142 Okaloosa Drive | $215,000 | 2023-12-07 | 1974 | 1,639 |
| 298 Okaloosa Drive | $340,000 | 2023-05-24 | 1974 | 1,697 |
| 340 Okaloosa Drive | $420,000 | 2023-05-15 | 1967 | 3,382 |
| 121 Okaloosa Drive | $275,000 | 2023-01-11 | 1974 | 2,071 |
| 135 Okaloosa Drive | $250,000 | 2022-09-06 | 1974 | 1,266 |
| 248 Okaloosa Drive | $283,500 | 2022-03-18 | 1971 | 1,714 |
| 300 Okaloosa Drive | $245,000 | 2021-08-30 | 1963 | 1,448 |
| 155 Okaloosa Drive | $285,000 | 2021-07-05 | 1974 | 1,602 |
| 339 Okaloosa Dr | $270,000 | 2021-07-02 | 1972 | 1,984 |
| 151 Okaloosa Drive | $315,000 | 2021-02-24 | 1979 | 2,332 |
| 83 Okaloosa Drive | $230,000 | 2020-11-27 | 1974 | 1,903 |
| 198 Okaloosa Dr | $187,000 | 2020-05-29 | 1974 | 1,448 |
| 241 Okaloosa Drive | $186,500 | 2020-01-21 | 1961 | 2,012 |
| 141 Okaloosa Drive | $169,500 | 2019-10-31 | 1974 | 1,422 |
| 345 Okaloosa Drive | $235,000 | 2018-08-23 | 1968 | 2,321 |
Communities along Okaloosa Drive
- Eloise Woods · 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 15, 2026. Listings appear courtesy of the listing brokerage under IDX rules; information deemed reliable but not guaranteed. See also all 850 homes for sale in Winter Haven, homes for sale in 33884.