Winding Trail, Kissimmee, FL
Everything we know about Winding Trail in Kissimmee: 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.
44 homes sit on Winding Trail in Kissimmee, FL (ZIP 34746), built 2003–2005, a typical 1,923 sq ft with 4 bedrooms. 1 is for sale right now from $310,000. Homes that sold since 2023 went for a median $345,000.
For sale on Winding Trail now
The homes on Winding Trail
44 single-family. Built by decade: 2000s 44.
Last recorded sales (parcel record)
| Address | Sold | Date | Built | Sq ft |
|---|---|---|---|---|
| 3030 Winding Trail | $277,000 | 2026-02-26 | 2004 | 1,687 |
| 3010 Winding Trail | $345,000 | 2025-12-19 | 2003 | 2,254 |
| 3181 Winding Trail | $329,800 | 2025-11-24 | 2004 | 1,923 |
| 3140 Winding Trail | $398,000 | 2023-08-24 | 2004 | 1,687 |
| 2990 Winding Trail | $375,000 | 2023-04-14 | 2004 | 2,034 |
| 3240 Winding Trail | $420,000 | 2022-01-27 | 2004 | 2,946 |
| 2900 Winding Trail | $413,000 | 2021-12-20 | 2003 | 1,923 |
| 3311 Winding Trail | $350,000 | 2021-12-15 | 2005 | 2,154 |
| 3080 Winding Trail | $308,000 | 2021-08-13 | 2004 | 1,687 |
| 3011 Winding Trail | $351,000 | 2021-07-21 | 2004 | 2,244 |
| 2941 Winding Trail | $275,500 | 2021-06-28 | 2004 | 1,687 |
| 3040 Winding Trail | $275,000 | 2021-05-19 | 2004 | 1,720 |
| 2930 Winding Trail | $240,000 | 2021-01-06 | 2004 | 2,010 |
| 3220 Winding Trail | $222,500 | 2020-11-12 | 2004 | 1,556 |
| 3251 Winding Trail | $234,500 | 2020-11-10 | 2004 | 1,923 |
| 3081 Winding Trail | $360,000 | 2020-10-09 | 2004 | 2,946 |
| 3041 Winding Trail | $220,000 | 2020-05-29 | 2004 | 1,923 |
| 2920 Winding Trail | $229,900 | 2020-02-27 | 2004 | 2,014 |
| 3100 Winding Trail | $275,000 | 2019-05-28 | 2003 | 1,923 |
| 3281 Winding Trail | $214,750 | 2018-09-07 | 2005 | 1,556 |
Communities along Winding Trail
- bellalago · 26 homes on the street
- bellalago · 4 homes on the street
- bellalago · 2 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 3,084 homes for sale in Kissimmee, homes for sale in 34746.