Isleworth Country Club Drive, Windermere, FL
Everything we know about Isleworth Country Club 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.
53 homes sit on Isleworth Country Club Drive in Windermere, FL (ZIP 34786), built 1987–2017, a typical 6,993 sq ft with 5 bedrooms. Nothing is listed for sale on the street today. 1 closed in the last 12 months at a median of $5,000,000. Homes that sold since 2023 went for a median $4,950,000.
Recent sales on Isleworth Country Club Drive
| Address | Sold | Closed | Beds / baths | Sq ft |
|---|---|---|---|---|
| 5104 Isleworth Country Club Drive | $5,000,000 | 2026-05-31 | 4 / 6.0 | 9,636 |
The homes on Isleworth Country Club Drive
53 single-family. Built by decade: 1980s 14, 1990s 21, 2000s 15, 2010s 3.
Last recorded sales (parcel record)
| Address | Sold | Date | Built | Sq ft |
|---|---|---|---|---|
| 5104 Isleworth Country Club Drive | $5,000,000 | 2026-05-31 | 2002 | 9,636 |
| 5525 Isleworth Country Club Drive | $11,500,000 | 2026-05-15 | 1999 | 9,511 |
| 5271 Isleworth Country Club Drive | $8,500,000 | 2025-09-05 | 2013 | 11,403 |
| 5056 Isleworth Country Club Drive | $3,700,000 | 2025-04-04 | 1987 | 4,225 |
| 5379 Isleworth Country Club Drive | $2,625,000 | 2025-02-07 | 1989 | 3,872 |
| 5092 Isleworth Country Club Drive | $4,000,000 | 2024-12-17 | 1995 | 6,115 |
| 5243 Isleworth Country Club Drive | $5,250,000 | 2024-08-20 | 1992 | 6,424 |
| 5084 Isleworth Country Club Drive | $4,075,000 | 2024-05-21 | 1999 | 7,159 |
| 5200 Isleworth Country Club Drive | $7,000,000 | 2024-03-04 | 2003 | 9,482 |
| 5226 Isleworth Country Club Drive | $4,950,000 | 2024-02-15 | 2001 | 7,821 |
| 5373 Isleworth Country Club Drive | $3,000,000 | 2024-01-12 | 1998 | 5,372 |
| 5139 Isleworth Country Club Dr | $6,400,000 | 2023-06-28 | 2002 | 13,973 |
| 5237 Isleworth Country Club Drive | $3,000,000 | 2023-01-31 | 1989 | 5,972 |
| 5103 Isleworth Country Club Drive | $4,850,000 | 2022-04-04 | 1996 | 8,397 |
| 5318 Isleworth Country Club Drive | $5,875,000 | 2021-08-09 | 2006 | 12,298 |
| 5284 Isleworth Country Club Drive | $3,000,000 | 2021-05-14 | 1996 | 6,738 |
| 5305 Isleworth Country Club Drive | $3,200,000 | 2021-05-05 | 2001 | 7,463 |
| 5372 Isleworth Country Club Drive | $4,030,000 | 2021-02-25 | 2004 | 13,230 |
| 5317 Isleworth Country Club Drive | $2,280,000 | 2021-02-12 | 1989 | 6,189 |
| 5091 Isleworth Country Club Drive | $2,500,000 | 2020-11-30 | 1996 | 6,423 |
Communities along Isleworth Country Club Drive
- Isleworth · 47 homes on the street
- Isleworth · 4 homes on the street
- Isleworth · 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 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.