Santa Rosa Drive, Winter Haven, FL
Everything we know about Santa Rosa 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.
44 homes sit on Santa Rosa Drive in Winter Haven, FL (ZIP 33884), built 1986–2001, a typical 2,324 sq ft with 4 bedrooms. 2 are for sale right now from $415,000 to $445,000. Homes that sold since 2023 went for a median $440,000.
For sale on Santa Rosa Drive now
The homes on Santa Rosa Drive
44 single-family. Built by decade: 1980s 33, 1990s 10, 2000s 1.
Last recorded sales (parcel record)
| Address | Sold | Date | Built | Sq ft |
|---|---|---|---|---|
| 262 Santa Rosa Drive | $280,000 | 2026-07-06 | 1987 | 2,336 |
| 205 Santa Rosa Drive | $480,000 | 2025-11-13 | 1986 | 2,251 |
| 228 Santa Rosa Drive | $472,000 | 2025-02-27 | 1992 | 2,335 |
| 234 Santa Rosa Drive | $440,000 | 2024-08-16 | 1989 | 2,792 |
| 240 Santa Rosa Drive | $440,000 | 2024-04-18 | 1988 | 2,850 |
| 261 Santa Rosa Drive | $500,000 | 2023-11-17 | 1990 | 3,306 |
| 232 Santa Rosa Drive | $376,500 | 2023-08-14 | 1988 | 2,312 |
| 249 Santa Rosa Drive | $385,000 | 2023-01-13 | 1989 | 1,900 |
| 223 Santa Rosa Drive | $435,200 | 2022-10-27 | 1987 | 2,314 |
| 278 Santa Rosa Dr | $350,000 | 2022-10-21 | 1987 | 1,943 |
| 250 Santa Rosa Drive | $435,000 | 2022-08-22 | 1989 | 2,732 |
| 221 Santa Rosa Drive | $358,500 | 2022-05-23 | 1987 | 1,894 |
| 274 Santa Rosa Drive | $350,000 | 2022-03-30 | 1986 | 2,388 |
| 280 Santa Rosa Drive | $355,000 | 2022-01-31 | 1986 | 2,251 |
| 230 Santa Rosa Drive | $305,000 | 2021-10-04 | 1990 | 2,185 |
| 222 Santa Rosa Drive | $269,900 | 2021-03-30 | 1988 | 1,981 |
| 224 Santa Rosa Drive | $263,000 | 2020-12-11 | 1987 | 2,025 |
| 270 Santa Rosa Drive | $228,000 | 2020-07-13 | 1986 | 2,050 |
| 258 Santa Rosa Drive | $222,000 | 2019-11-01 | 1991 | 2,598 |
| 272 Santa Rosa Drive | $290,000 | 2019-05-21 | 1988 | 3,018 |
Communities along Santa Rosa Drive
- Overlook Estates · 32 homes on the street
- Overlook Estates · 3 homes on the street
- Overlook Estates · 3 homes on the street
- Overlook Estates · 2 homes on the street
- Overlook Estates · 1 homes on the street
- Overlook Estates · 1 homes on the street
- Overlook Estates · 1 homes on the street
- Overlook Estates · 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.