Winners Circle, Cantonment, FL
Everything we know about Winners Circle in Cantonment: 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.
49 homes sit on Winners Circle in Cantonment, FL (ZIP 32533), built 1997–1999, a typical 1,803 sq ft with 3 bedrooms. Nothing is listed for sale on the street today. 4 closed in the last 12 months at a median of $295,000. Homes that sold since 2023 went for a median $299,500.
Recent sales on Winners Circle
| Address | Sold | Closed | Beds / baths | Sq ft |
|---|---|---|---|---|
| 2040 Winners Cir | $290,000 | 2026-08-25 | 4 / 2.0 | 1,901 |
| 2032 Winners Cir | $310,000 | 2026-06-30 | 3 / 2.0 | 2,165 |
| 1935 Winners Cir | $300,000 | 2026-03-05 | 4 / 2.0 | 2,087 |
| 2000 Winners Cir | $280,000 | 2025-11-03 | 3 / 2.0 | 1,607 |
The homes on Winners Circle
49 single-family. Built by decade: 1990s 49.
Last recorded sales (parcel record)
| Address | Sold | Date | Built | Sq ft |
|---|---|---|---|---|
| 2040 Winners Cir | $290,000 | 2026-08-25 | 1999 | 1,901 |
| 2032 Winners Cir | $310,000 | 2026-06-30 | 1997 | 2,165 |
| 1935 Winners Cir | $300,000 | 2026-03-05 | 1997 | 2,087 |
| 2000 Winners Cir | $280,000 | 2025-11-03 | 1998 | 1,607 |
| 2081 Winners Cir | $295,000 | 2024-12-03 | 1998 | 1,800 |
| 1920 Winners Cir | $305,000 | 2024-08-09 | 1997 | 1,889 |
| 2016 Winners Cir | $350,000 | 2024-03-26 | 1999 | 1,782 |
| 2072 Winners Cir | $299,500 | 2023-03-20 | 1997 | 1,860 |
| 1996 Winners Cir | $294,000 | 2023-01-24 | 1998 | 1,900 |
| 1988 Winners Cir | $295,000 | 2022-12-21 | 1998 | 1,847 |
| 2075 Winners Cir | $270,000 | 2022-11-02 | 1997 | 1,463 |
| 2045 Winners Cir | $329,000 | 2022-05-20 | 1998 | 1,706 |
| 2061 Winners Cir | $269,000 | 2022-01-20 | 1999 | 1,740 |
| 1929 Winners Circle | $275,000 | 2021-11-01 | 1997 | 1,530 |
| 1972 Winners Cir | $230,000 | 2021-10-06 | 1998 | 1,613 |
| 1992 Winners Cir | $259,000 | 2021-09-30 | 1997 | 1,908 |
| 1959 Winners Cir | $159,900 | 2020-12-23 | 1997 | 1,882 |
| 2024 Winners Cir | $193,000 | 2020-09-04 | 1997 | 1,872 |
| 1948 Winners Cir | $250,000 | 2020-07-31 | 1999 | 2,078 |
| 1956 Winners Cir | $189,900 | 2019-12-19 | 1999 | 1,706 |
Communities along Winners Circle
- Churchill · 49 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 158 homes for sale in Cantonment, homes for sale in 32533.