Grand Cayman Circle, Winter Haven, FL
Everything we know about Grand Cayman Circle 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.
38 homes sit on Grand Cayman Circle in Winter Haven, FL (ZIP 33884), built 1985–2005, a typical 1,676 sq ft with 3 bedrooms. 1 is for sale right now from $359,000. Homes that sold since 2023 went for a median $280,000.
For sale on Grand Cayman Circle now
The homes on Grand Cayman Circle
38 single-family. Built by decade: 1980s 16, 1990s 19, 2000s 3.
Last recorded sales (parcel record)
| Address | Sold | Date | Built | Sq ft |
|---|---|---|---|---|
| 1454 Grand Cayman Circle | $245,000 | 2026-08-14 | 1987 | 1,596 |
| 1458 Grand Cayman Circle | $280,000 | 2026-02-11 | 1996 | 1,615 |
| 1423 Grand Cayman Circle | $263,000 | 2025-05-13 | 1990 | 1,588 |
| 1437 Grand Cayman Circle | $465,000 | 2025-04-10 | 1989 | 1,785 |
| 1422 Grand Cayman Circle | $281,500 | 2024-12-09 | 1990 | 1,615 |
| 1463 Grand Cayman Circle | $365,000 | 2024-10-22 | 1991 | 1,895 |
| 1460 Grand Cayman Circle | $265,000 | 2024-06-20 | 1988 | 1,360 |
| 1405 Grand Cayman Circle | $260,000 | 2024-04-23 | 1993 | 1,450 |
| 1449 Grand Cayman Circle | $306,000 | 2023-06-20 | 1993 | 1,583 |
| 1479 Grand Cayman Circle | $255,000 | 2022-08-08 | 1987 | 2,013 |
| 1434 Grand Cayman Circle | $269,000 | 2021-10-10 | 1986 | 1,908 |
| 1420 Grand Cayman Circle | $272,000 | 2021-10-01 | 1986 | 1,909 |
| 1457 Grand Cayman Circle | $235,000 | 2021-05-14 | 1988 | 1,469 |
| 1425 Grand Cayman Circle | $245,000 | 2021-03-11 | 1986 | 1,834 |
| 1475 Grand Cayman Circle | $295,000 | 2021-02-12 | 1996 | 2,066 |
| 1441 Grand Cayman Circle | $339,000 | 2020-10-09 | 1990 | 2,634 |
| 1469 Grand Cayman Circle | $211,000 | 2020-06-04 | 1993 | 1,823 |
| 1456 Grand Cayman Circle | $175,000 | 2020-04-27 | 1995 | 1,703 |
| 1407 Grand Cayman Circle | $165,000 | 2019-12-23 | 1986 | 1,614 |
| 1447 Grand Cayman Circle | $215,000 | 2019-08-23 | 1998 | 1,752 |
Communities along Grand Cayman Circle
- Lake Dexter Moorings · 37 homes on the street
- Lake Dexter Moorings · 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 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 33884.