Leisure Drive, Winter Haven, FL
Everything we know about Leisure 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.
25 homes sit on Leisure Drive in Winter Haven, FL (ZIP 33881), built 1963–1999, a typical 1,728 sq ft with 3 bedrooms. 1 is for sale right now from $675,000. Homes that sold since 2023 went for a median $290,000.
For sale on Leisure Drive now
The homes on Leisure Drive
24 single-family, 1 condo/townhome/other. Built by decade: 1960s 16, 1970s 8, 1990s 1.
Last recorded sales (parcel record)
| Address | Sold | Date | Built | Sq ft |
|---|---|---|---|---|
| 2004 Leisure Drive | $370,000 | 2026-01-05 | 1978 | 2,312 |
| 2023 Leisure Drive | $260,000 | 2025-12-23 | 1964 | 1,410 |
| 2036 Leisure Drive | $220,000 | 2025-01-24 | 1964 | 1,140 |
| 2022 Leisure Drive | $525,000 | 2024-07-15 | 1972 | 1,770 |
| 2044 Leisure Drive | $290,000 | 2023-11-07 | 1963 | 1,499 |
| 2030 Leisure Drive | $290,000 | 2023-09-26 | 1964 | 1,814 |
| 2034 Leisure Drive | $275,000 | 2023-07-25 | 1964 | 1,928 |
| 2042 Leisure Drive | $186,000 | 2022-12-06 | 1963 | 1,959 |
| 2017 Leisure Drive | $291,000 | 2022-12-02 | 1974 | 1,901 |
| 2029 Leisure Drive | $189,900 | 2021-02-19 | 1963 | 1,479 |
| 2028 Leisure Drive | $168,900 | 2019-08-19 | 1965 | 1,700 |
| 2015 Leisure Drive | $175,000 | 2018-11-30 | 1967 | 1,688 |
| 2014 Leisure Drive | $230,000 | 2018-06-14 | 1968 | 2,191 |
| 2025 Leisure Drive | $130,400 | 2017-10-31 | 1963 | 1,499 |
| 2040 Leisure Drive | $85,000 | 2014-10-27 | 1963 | 1,221 |
| 2032 Leisure Drive | $135,000 | 2014-02-03 | 1964 | 1,862 |
| 2001 Leisure Drive | $102,500 | 2013-11-13 | 1966 | 1,728 |
| 2038 Leisure Drive | $119,900 | 2013-08-22 | 1963 | 1,758 |
| 2002 Leisure Drive | $235,000 | 2013-01-11 | 1973 | 2,523 |
| 2012 Leisure Drive | $162,500 | 2012-10-16 | 1971 | 1,844 |
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 784 homes for sale in Winter Haven, homes for sale in 33881.