Winfield Drive, Kissimmee, FL
Everything we know about Winfield Drive 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.
33 homes sit on Winfield Drive in Kissimmee, FL (ZIP 34743), built 1995–1999, a typical 1,913 sq ft with 4 bedrooms. Nothing is listed for sale on the street today. 1 closed in the last 12 months at a median of $395,000. Homes that sold since 2023 went for a median $395,500.
Recent sales on Winfield Drive
| Address | Sold | Closed | Beds / baths | Sq ft |
|---|---|---|---|---|
| 2472 Winfield Drive | $395,000 | 2026-01-30 | 4 / 2.0 | 2,023 |
The homes on Winfield Drive
33 single-family. Built by decade: 1990s 33.
Last recorded sales (parcel record)
| Address | Sold | Date | Built | Sq ft |
|---|---|---|---|---|
| 2472 Winfield Drive | $395,000 | 2026-01-30 | 1999 | 2,023 |
| 2438 Winfield Drive | $419,000 | 2025-05-29 | 1996 | 1,693 |
| 2475 Winfield Drive | $369,000 | 2024-08-02 | 1998 | 1,550 |
| 2461 Winfield Drive | $350,000 | 2023-10-13 | 1999 | 2,331 |
| 2405 Winfield Drive | $396,000 | 2023-03-24 | 1996 | 1,947 |
| 2439 Winfield Drive | $410,000 | 2023-02-21 | 1996 | 1,693 |
| 2445 Winfield Drive | $345,000 | 2022-10-18 | 1998 | 2,030 |
| 2453 Winfield Drive | $450,000 | 2022-04-18 | 1998 | 2,331 |
| 2465 Winfield Drive | $335,000 | 2021-12-29 | 1997 | 1,756 |
| 2455 Winfield Drive | $350,000 | 2021-10-14 | 1998 | 2,330 |
| 2446 Winfield Drive | $335,000 | 2021-10-08 | 1997 | 1,921 |
| 2469 Winfield Drive | $243,000 | 2020-03-11 | 1998 | 1,921 |
| 2423 Winfield Drive | $240,000 | 2019-09-13 | 1996 | 1,693 |
| 2435 Winfield Drive | $225,000 | 2019-06-27 | 1995 | 1,693 |
| 2474 Winfield Drive | $265,000 | 2019-03-15 | 1997 | 2,331 |
| 2403 Winfield Drive | $237,000 | 2019-01-29 | 1997 | 1,550 |
| 2471 Winfield Drive | $196,000 | 2018-01-29 | 1999 | 1,802 |
| 2479 Winfield Drive | $190,000 | 2016-09-09 | 1999 | 1,642 |
| 2477 Winfield Drive | $190,000 | 2016-01-11 | 1999 | 1,802 |
| 2470 Winfield Drive | $188,000 | 2015-05-18 | 1998 | 2,331 |
Communities along Winfield Drive
- Westlake Hammock · 15 homes on the street
- Westlake Hammock · 10 homes on the street
- Westlake Hammock · 6 homes on the street
- Westlake Hammock · 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 14, 2026. Listings appear courtesy of the listing brokerage under IDX rules; information deemed reliable but not guaranteed. See also all 2,917 homes for sale in Kissimmee, homes for sale in 34743.