Winchester Boulevard, Kissimmee, FL
Everything we know about Winchester Boulevard 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.
39 homes sit on Winchester Boulevard in Kissimmee, FL (ZIP 34743), built 1996–2000, a typical 1,642 sq ft with 3 bedrooms. Nothing is listed for sale on the street today. 3 closed in the last 12 months at a median of $235,000. Homes that sold since 2023 went for a median $360,000.
Recent sales on Winchester Boulevard
| Address | Sold | Closed | Beds / baths | Sq ft |
|---|---|---|---|---|
| 2481 Winchester Boulevard | $235,000 | 2026-10-01 | 3 / 2.0 | 1,023 |
| 2481 Winchester Boulevard | $235,000 | 2026-10-01 | 3 / 2.0 | 1,023 |
| 2400 Winchester Boulevard | $360,000 | 2026-05-08 | 3 / 2.0 | 1,405 |
The homes on Winchester Boulevard
39 single-family. Built by decade: 1990s 38, 2000s 1.
Last recorded sales (parcel record)
| Address | Sold | Date | Built | Sq ft |
|---|---|---|---|---|
| 2481 Winchester Boulevard | $235,000 | 2026-10-01 | 1997 | 1,023 |
| 2400 Winchester Boulevard | $360,000 | 2026-05-08 | 2000 | 1,405 |
| 2434 Winchester Boulevard | $360,000 | 2025-03-03 | 1999 | 1,802 |
| 2404 Winchester Boulevard | $400,000 | 2024-01-16 | 1997 | 1,622 |
| 2460 Winchester Boulevard | $375,000 | 2023-12-19 | 1996 | 1,642 |
| 2446 Winchester Boulevard | $385,000 | 2023-06-13 | 1998 | 1,802 |
| 2470 Winchester Boulevard | $305,000 | 2023-03-13 | 1996 | 1,196 |
| 2438 Winchester Boulevard | $405,000 | 2022-11-14 | 1998 | 1,802 |
| 2424 Winchester Boulevard | $385,000 | 2022-09-16 | 1998 | 1,802 |
| 2426 Winchester Boulevard | $260,000 | 2021-03-16 | 1998 | 1,405 |
| 2442 Winchester Boulevard | $242,000 | 2021-02-25 | 1999 | 1,240 |
| 2468 Winchester Boulevard | $245,000 | 2020-12-21 | 1996 | 1,413 |
| 2414 Winchester Boulevard | $265,000 | 2020-11-13 | 1997 | 1,642 |
| 2416 Winchester Boulevard | $265,000 | 2020-04-30 | 1998 | 1,802 |
| 2415 Winchester Boulevard | $211,000 | 2019-09-09 | 1998 | 1,466 |
| 2466 Winchester Blvd | $222,000 | 2019-05-03 | 1996 | 1,642 |
| 2447 Winchester Boulevard | $225,000 | 2019-04-09 | 1998 | 1,240 |
| 2410 Winchester Blvd | $205,000 | 2018-07-12 | 1997 | 1,240 |
| 2402 Winchester Boulevard | $220,000 | 2018-07-09 | 1997 | 1,622 |
| 2444 Winchester Boulevard | $232,000 | 2018-06-11 | 1998 | 1,802 |
Communities along Winchester Boulevard
- Remington Pointe · 11 homes on the street
- Remington Pointe · 10 homes on the street
- Remington Pointe · 8 homes on the street
- Remington Pointe · 5 homes on the street
- Remington Pointe · 3 homes on the street
- Remington Pointe · 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 3,084 homes for sale in Kissimmee, homes for sale in 34743.