Sir Winston Way, Orlando, FL
Everything we know about Sir Winston Way in Orlando: 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 Sir Winston Way in Orlando, FL (ZIP 32824), built 1992–1998, a typical 2,166 sq ft with 4 bedrooms. Nothing is listed for sale on the street today. Homes that sold since 2023 went for a median $425,000.
The homes on Sir Winston Way
37 single-family, 1 condo/townhome/other. Built by decade: 1990s 38.
Last recorded sales (parcel record)
| Address | Sold | Date | Built | Sq ft |
|---|---|---|---|---|
| 11646 Sir Winston Way | $418,000 | 2026-02-03 | 1994 | 1,847 |
| 11736 Sir Winston Way | $425,000 | 2025-11-03 | 1998 | 1,852 |
| 11831 Sir Winston Way | $412,000 | 2024-10-01 | 1996 | 1,596 |
| 11791 Sir Winston Way | $527,000 | 2024-08-07 | 1993 | 2,174 |
| 11780 Sir Winston Way | $475,000 | 2024-05-29 | 1993 | 2,103 |
| 11808 Sir Winston Way | $520,000 | 2024-01-12 | 1993 | 2,348 |
| 11729 Sir Winston Way | $430,000 | 2023-11-30 | 1993 | 1,998 |
| 11748 Sir Winston Way | $350,000 | 2023-08-31 | 1993 | 2,346 |
| 11711 Sir Winston Way | $375,000 | 2023-04-04 | 1993 | 2,438 |
| 11718 Sir Winston Way | $420,000 | 2022-08-10 | 1994 | 2,363 |
| 11614 Sir Winston Way | $415,000 | 2021-09-17 | 1994 | 2,204 |
| 11627 Sir Winston Way | $290,000 | 2021-01-25 | 1998 | 1,952 |
| 11837 Sir Winston Way | $315,000 | 2020-06-30 | 1992 | 2,395 |
| 11699 Sir Winston Way | $275,000 | 2020-06-18 | 1993 | 2,067 |
| 11658 Sir Winston Way | $275,000 | 2020-03-04 | 1993 | 2,158 |
| 11693 Sir Winston Way | $286,000 | 2019-07-29 | 1998 | 1,907 |
| 11687 Sir Winston Way | $284,000 | 2019-07-11 | 1992 | 2,246 |
| 11838 Sir Winston Way | $280,000 | 2019-05-07 | 1997 | 2,110 |
| 11826 Sir Winston Way | $245,100 | 2019-04-26 | 1996 | 2,092 |
| 11609 Sir Winston Way | $283,000 | 2018-12-21 | 1993 | 2,304 |
Communities along Sir Winston Way
- Southchase · 21 homes on the street
- Southchase · 8 homes on the street
- Southchase · 4 homes on the street
- Southchase · 3 homes on the street
- Southchase · 1 homes on the street
- Southchase · 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 4,337 homes for sale in Orlando, homes for sale in 32824.