Jailene Drive, Windermere, FL
Everything we know about Jailene Drive in Windermere: 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.
37 homes sit on Jailene Drive in Windermere, FL (ZIP 34786), built 2007–2013, a typical 2,580 sq ft with 4 bedrooms. Nothing is listed for sale on the street today. Homes that sold since 2023 went for a median $670,000.
The homes on Jailene Drive
31 single-family, 6 condo/townhome/other. Built by decade: 2000s 6, 2010s 31.
Last recorded sales (parcel record)
| Address | Sold | Date | Built | Sq ft |
|---|---|---|---|---|
| 8104 Jailene Drive | $759,000 | 2026-10-09 | 2012 | 2,886 |
| 7906 Jailene Drive | $695,000 | 2026-09-11 | 2011 | 2,618 |
| 8146 Jailene Drive | $555,000 | 2026-08-06 | 2012 | 2,099 |
| 8014 Jailene Drive | $580,000 | 2024-08-30 | 2012 | 2,322 |
| 7949 Jailene Dr | $670,000 | 2023-12-11 | 2012 | 3,015 |
| 8170 Jailene Dr | $631,000 | 2022-11-08 | 2012 | 2,580 |
| 7733 Jailene Drive | $417,000 | 2022-08-31 | 2007 | 1,724 |
| 8020 Jailene Drive | $664,000 | 2022-07-29 | 2012 | 2,761 |
| 8165 Jailene Dr | $725,000 | 2022-04-25 | 2013 | 2,975 |
| 8122 Jailene Drive | $465,000 | 2021-07-06 | 2012 | 2,226 |
| 7912 Jailene Drive | $515,000 | 2021-03-15 | 2011 | 2,750 |
| 8129 Jailene Drive | $428,000 | 2021-03-05 | 2013 | 3,004 |
| 8153 Jailene Drive | $391,800 | 2021-01-12 | 2012 | 2,286 |
| 8026 Jailene Drive | $450,000 | 2020-04-08 | 2012 | 2,580 |
| 7935 Jailene Drive | $425,500 | 2019-11-15 | 2012 | 2,922 |
| 7961 Jailene Drive | $375,000 | 2019-09-06 | 2012 | 2,585 |
| 7924 Jailene Drive | $400,000 | 2019-03-01 | 2012 | 3,044 |
| 8147 Jailene Drive | $355,000 | 2019-01-25 | 2013 | 2,226 |
| 8111 Jailene Drive | $325,000 | 2018-12-28 | 2012 | 1,922 |
| 8182 Jailene Drive | $339,500 | 2018-09-26 | 2012 | 2,189 |
Communities along Jailene Drive
- Lake Sawyer South · 14 homes on the street
- Lake Sawyer South · 12 homes on the street
- Lake Sawyer South · 6 homes on the street
- Lake Sawyer South · 1 homes on the street
- Lake Sawyer South · 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 236 homes for sale in Windermere, homes for sale in 34786.