Winter Stay Drive, Winter Garden, FL
Everything we know about Winter Stay Drive in Winter Garden: 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.
66 homes sit on Winter Stay Drive in Winter Garden, FL (ZIP 34787), built 2015–2021, a typical 2,935 sq ft with 4 bedrooms. 2 are for sale right now from $835,000 to $1,200,000. 1 closed in the last 12 months at a median of $830,000. Homes that sold since 2023 went for a median $730,000.
For sale on Winter Stay Drive now
Recent sales on Winter Stay Drive
| Address | Sold | Closed | Beds / baths | Sq ft |
|---|---|---|---|---|
| 14831 Winter Stay Drive | $830,000 | 2026-04-10 | 5 / 3.0 | 2,662 |
The homes on Winter Stay Drive
65 single-family, 1 condo/townhome/other. Built by decade: 2010s 64, 2020s 2.
Last recorded sales (parcel record)
| Address | Sold | Date | Built | Sq ft |
|---|---|---|---|---|
| 14831 Winter Stay Drive | $830,000 | 2026-04-10 | 2018 | 2,662 |
| 14507 Winter Stay Drive | $1,150,000 | 2025-11-05 | 2021 | 3,950 |
| 14639 Winter Stay Drive | $665,000 | 2025-08-15 | 2018 | 2,468 |
| 14513 Winter Stay Drive | $1,000,000 | 2025-08-01 | 2020 | 4,305 |
| 14554 Winter Stay Drive | $700,000 | 2025-06-30 | 2015 | 3,035 |
| 14657 Winter Stay Drive | $660,000 | 2025-04-21 | 2018 | 2,935 |
| 14627 Winter Stay Drive | $642,000 | 2025-03-03 | 2017 | 2,072 |
| 14969 Winter Stay Drive | $990,000 | 2025-03-03 | 2018 | 3,443 |
| 14891 Winter Stay Drive | $685,000 | 2024-09-06 | 2018 | 2,662 |
| 14548 Winter Stay Drive | $1,185,000 | 2024-07-26 | 2018 | 4,337 |
| 14975 Winter Stay Drive | $695,000 | 2024-04-05 | 2019 | 2,662 |
| 14981 Winter Stay Drive | $760,000 | 2023-12-15 | 2019 | 2,656 |
| 14711 Winter Stay Drive | $700,000 | 2023-11-16 | 2019 | 2,662 |
| 14843 Winter Stay Drive | $940,000 | 2023-08-21 | 2018 | 3,505 |
| 14693 Winter Stay Drive | $580,000 | 2022-09-09 | 2017 | 2,072 |
| 14609 Winter Stay Drive | $700,000 | 2022-02-11 | 2018 | 2,935 |
| 14747 Winter Stay Drive | $585,000 | 2021-12-03 | 2019 | 2,662 |
| 14543 Winter Stay Drive | $629,000 | 2021-11-18 | 2016 | 2,930 |
| 14608 Winter Stay Drive | $595,000 | 2021-10-08 | 2017 | 2,921 |
| 14560 Winter Stay Drive | $587,500 | 2021-08-02 | 2017 | 2,924 |
Communities along Winter Stay Drive
- Panther View · 19 homes on the street
- Panther View · 14 homes on the street
- Watermark · 12 homes on the street
- Watermark · 9 homes on the street
- Watermark · 7 homes on the street
- Panther View · 3 homes on the street
- Watermark · 1 homes on the street
- Watermark · 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 750 homes for sale in Winter Garden, homes for sale in 34787.