Windermere Drive, Jacksonville, FL
Everything we know about Windermere Drive in Jacksonville: 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.
49 homes sit on Windermere Drive in Jacksonville, FL (ZIP 32211), built 1925–2017, a typical 1,300 sq ft with 3 bedrooms. Nothing is listed for sale on the street today. Homes that sold since 2023 went for a median $162,500.
The homes on Windermere Drive
28 single-family, 21 condo/townhome/other. Built by decade: 1920s 2, 1930s 1, 1940s 1, 1950s 40, 1960s 2, 1990s 1, 2000s 1, 2010s 1.
Last recorded sales (parcel record)
| Address | Sold | Date | Built | Sq ft |
|---|---|---|---|---|
| 5540 Windermere Drive | $247,500 | 2025-09-30 | 1950 | 1,244 |
| 5426 Windermere Drive | $132,500 | 2025-04-21 | 1950 | 950 |
| 5835 Windermere Drive | $160,000 | 2025-03-13 | 1953 | 1,468 |
| 5425 Windermere Drive | $165,000 | 2024-05-31 | 1950 | 1,197 |
| 5663 Windermere Drive | $371,500 | 2022-10-24 | 1925 | 1,887 |
| 5408 Windermere Drive | $275,000 | 2022-08-10 | 1950 | 1,128 |
| 5477 Windermere Drive | $165,000 | 2021-04-12 | 1950 | 1,300 |
| 5460 Windermere Drive | $165,000 | 2021-03-11 | 1950 | 1,134 |
| 5565 Windermere Drive | $118,000 | 2020-12-04 | 1950 | 1,520 |
| 5444 Windermere Drive | $129,000 | 2020-10-29 | 1950 | 828 |
| 5819 Windermere Drive | $115,000 | 2020-09-25 | 1961 | 1,540 |
| 5834 Windermere Drive | $180,000 | 2020-07-29 | 1953 | 1,753 |
| 5524 Windermere Drive | $156,000 | 2020-03-17 | 1950 | 1,506 |
| 5855 Windermere Drive | $165,000 | 2019-12-27 | 1953 | 1,422 |
| 5514 Windermere Drive | $105,000 | 2018-09-05 | 1950 | 1,214 |
| 5823 Windermere Drive | $120,000 | 2018-07-31 | 1961 | 1,050 |
| 5451 Windermere Drive | $110,000 | 2017-11-10 | 1950 | 970 |
| 5539 Windermere Drive | $188,000 | 2017-07-31 | 2017 | 1,760 |
| 5629 Windermere Drive | $101,000 | 2016-11-10 | 1939 | 1,502 |
| 5400 Windermere Drive | $53,000 | 2014-07-28 | 1950 | 1,789 |
Communities along Windermere Drive
- River Forest · 16 homes on the street
- River Forest · 12 homes on the street
- Eggleston Heights · 6 homes on the street
- Eggleston Heights · 3 homes on the street
- Floral Bluff · 1 homes on the street
- Loretta Jeanne · 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 September 26, 2026. Listings appear courtesy of the listing brokerage under IDX rules; information deemed reliable but not guaranteed. See also all 3,941 homes for sale in Jacksonville, homes for sale in 32211.