Carefree Cove Drive, Winter Haven, FL
Everything we know about Carefree Cove 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.
42 homes sit on Carefree Cove Drive in Winter Haven, FL (ZIP 33881), built 1959–2026, a typical 1,295 sq ft with 3 bedrooms. 3 are for sale right now from $200,000 to $319,900. Homes that sold since 2023 went for a median $245,450.
For sale on Carefree Cove Drive now
The homes on Carefree Cove Drive
42 single-family. Built by decade: 1950s 3, 1960s 7, 1970s 19, 1980s 8, 2020s 5.
Last recorded sales (parcel record)
| Address | Sold | Date | Built | Sq ft |
|---|---|---|---|---|
| 1114 Carefree Cove Drive | $170,000 | 2026-09-28 | 1971 | 1,300 |
| 1130 Carefree Cove Drive | $261,999 | 2026-04-16 | 1961 | 1,204 |
| 1013 Carefree Cove Drive | $250,000 | 2025-09-15 | 1972 | 1,025 |
| 1139 Carefree Cove Drive | $362,500 | 2025-04-02 | 1979 | 1,291 |
| 1015 Carefree Cove Drive | $240,000 | 2024-10-04 | 1972 | 1,104 |
| 1098 Carefree Cove Drive | $225,000 | 2024-03-28 | 1969 | 1,115 |
| 1116 Carefree Cove Drive | $230,000 | 2024-01-11 | 1971 | 1,325 |
| 1094 Carefree Cove Drive | $240,900 | 2023-11-30 | 1970 | 1,080 |
| 1159 Carefree Cove Drive | $380,000 | 2023-11-30 | 1984 | 1,300 |
| 1103 Carefree Cove Drive | $290,000 | 2023-06-27 | 2023 | 1,338 |
| 1031 Carefree Cove Drive | $300,000 | 2022-11-22 | 2022 | 1,597 |
| 1099 Carefree Cove Drive | $300,000 | 2022-09-14 | 2022 | 1,500 |
| 1041 Carefree Cove Drive | $283,100 | 2022-05-06 | 2022 | 1,338 |
| 1171 Carefree Cove Drive | $319,000 | 2021-12-30 | 1984 | 1,450 |
| 1096 Carefree Cove Drive | $185,000 | 2021-10-11 | 1970 | 1,300 |
| 1142 Carefree Cove Drive | $152,000 | 2021-07-06 | 1961 | 1,204 |
| 1100 Carefree Cove Drive | $124,900 | 2021-03-25 | 1969 | 1,019 |
| 1153 Carefree Cove Drive | $130,000 | 2020-12-22 | 1984 | 1,096 |
| 1092 Carefree Cove Drive | $125,000 | 2019-05-20 | 1970 | 1,134 |
| 1163 Carefree Cove Drive | $114,900 | 2019-03-08 | 1985 | 2,044 |
Communities along Carefree Cove Drive
- CAREFREE Cove · 25 homes on the street
- CAREFREE Cove · 6 homes on the street
- CAREFREE Cove · 6 homes on the street
- CAREFREE Cove · 1 homes on the street
- CAREFREE Cove · 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 33881.