Sterling Drive, Winter Haven, FL
Everything we know about Sterling 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.
48 homes sit on Sterling Drive in Winter Haven, FL (ZIP 33884), built 1990–2001, a typical 1,814 sq ft with 3 bedrooms. Nothing is listed for sale on the street today. Homes that sold since 2023 went for a median $335,000.
The homes on Sterling Drive
48 single-family. Built by decade: 1990s 45, 2000s 3.
Last recorded sales (parcel record)
| Address | Sold | Date | Built | Sq ft |
|---|---|---|---|---|
| 343 Sterling Drive | $259,900 | 2026-07-02 | 1991 | 1,372 |
| 356 Sterling Drive | $330,000 | 2026-06-26 | 2001 | 1,535 |
| 341 Sterling Drive | $380,000 | 2026-04-16 | 1991 | 2,008 |
| 346 Sterling Drive | $345,000 | 2025-03-28 | 2000 | 1,929 |
| 384 Sterling Drive | $360,000 | 2024-08-30 | 1993 | 1,740 |
| 306 Sterling Drive | $375,000 | 2024-08-15 | 1990 | 1,972 |
| 376 Sterling Drive | $290,000 | 2024-06-21 | 1999 | 1,929 |
| 307 Sterling Drive | $335,000 | 2023-12-29 | 1997 | 1,444 |
| 308 Sterling Drive | $298,000 | 2023-08-16 | 1997 | 1,840 |
| 328 Sterling Drive | $335,000 | 2023-07-27 | 1991 | 1,560 |
| 304 Sterling Drive | $285,000 | 2023-06-12 | 1991 | 1,560 |
| 330 Sterling Drive | $279,900 | 2022-12-30 | 1997 | 1,426 |
| 324 Sterling Drive | $349,900 | 2022-08-19 | 1991 | 2,281 |
| 312 Sterling Drive | $320,000 | 2022-03-07 | 1997 | 2,072 |
| 372 Sterling Drive | $275,000 | 2021-08-27 | 1997 | 1,691 |
| 389 Sterling Drive | $217,500 | 2021-04-13 | 1992 | 1,582 |
| 365 Sterling Drive | $219,000 | 2021-04-09 | 1998 | 1,465 |
| 391 Sterling Drive | $240,000 | 2021-03-01 | 1990 | 1,848 |
| 345 Sterling Drive | $279,500 | 2020-12-03 | 1994 | 2,460 |
| 350 Sterling Drive | $243,000 | 2020-07-30 | 1994 | 1,639 |
Communities along Sterling Drive
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.