Rolling Oaks Drive, Winter Haven, FL
Everything we know about Rolling Oaks 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.
101 homes sit on Rolling Oaks Drive in Winter Haven, FL (ZIP 33880), built 1979–1987, a typical 1,104 sq ft with 2 bedrooms. 5 are for sale right now from $84,900 to $139,900. Homes that sold since 2023 went for a median $115,000.
For sale on Rolling Oaks Drive now
The homes on Rolling Oaks Drive
1 single-family, 100 condo/townhome/other. Built by decade: 1970s 4, 1980s 97.
Last recorded sales (parcel record)
| Address | Sold | Date | Built | Sq ft |
|---|---|---|---|---|
| 4063 Rolling Oaks Drive | $104,500 | 2026-09-30 | 1983 | 1,320 |
| 4027 Rolling Oaks Drive | $65,000 | 2026-08-14 | 1979 | 1,200 |
| 4150 Rolling Oaks Drive | $111,000 | 2026-06-05 | 1985 | 1,032 |
| 4155 Rolling Oaks Drive | $40,000 | 2026-05-11 | 1985 | 1,176 |
| 4135 Rolling Oaks Drive | $117,000 | 2026-05-05 | 1987 | 1,248 |
| 4161 Rolling Oaks Drive | $95,000 | 2026-04-07 | 1985 | 1,104 |
| 4192 Rolling Oaks Drive | $129,900 | 2026-03-31 | 1983 | 1,056 |
| 4115 Rolling Oaks Drive | $108,500 | 2026-02-18 | 1981 | 1,416 |
| 4077 Rolling Oaks Drive | $105,000 | 2026-01-08 | 1984 | 1,176 |
| 4067 Rolling Oaks Drive | $85,000 | 2025-12-23 | 1983 | 992 |
| 4090 Rolling Oaks Drive | $115,000 | 2025-12-03 | 1982 | 1,344 |
| 4034 Rolling Oaks Drive | $95,000 | 2025-10-22 | 1982 | 1,032 |
| 4153 Rolling Oaks Drive | $139,000 | 2025-10-21 | 1985 | 1,368 |
| 4113 Rolling Oaks Drive | $115,000 | 2025-10-02 | 1983 | 1,392 |
| 4190 Rolling Oaks Drive | $80,000 | 2025-06-20 | 1983 | 1,056 |
| 4082 Rolling Oaks Drive | $116,000 | 2025-06-04 | 1983 | 1,440 |
| 4065 Rolling Oaks Drive | $87,500 | 2025-05-20 | 1983 | 864 |
| 4076 Rolling Oaks Drive | $135,000 | 2025-04-23 | 1983 | 1,200 |
| 4189 Rolling Oaks Drive | $135,000 | 2025-03-28 | 1980 | 1,225 |
| 4129 Rolling Oaks Drive | $131,000 | 2025-01-29 | 1985 | 1,056 |
Communities along Rolling Oaks Drive
- OAKWOOD Estates · 95 homes on the street
- OAKWOOD Estates · 6 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 33880.