Windsong Oak Drive, Leesburg, FL
Everything we know about Windsong Oak Drive in Leesburg: 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.
70 homes sit on Windsong Oak Drive in Leesburg, FL (ZIP 34748), built 2006–2020, a typical 2,092 sq ft with 4 bedrooms. 1 is for sale right now from $295,000. 1 closed in the last 12 months at a median of $293,500. Homes that sold since 2023 went for a median $339,400.
For sale on Windsong Oak Drive now
Recent sales on Windsong Oak Drive
| Address | Sold | Closed | Beds / baths | Sq ft |
|---|---|---|---|---|
| 5546 Windsong Oak Drive | $293,500 | 2026-08-26 | 3 / 2.0 | 1,486 |
The homes on Windsong Oak Drive
67 single-family, 3 condo/townhome/other. Built by decade: 2000s 25, 2010s 39, 2020s 6.
Last recorded sales (parcel record)
| Address | Sold | Date | Built | Sq ft |
|---|---|---|---|---|
| 5546 Windsong Oak Drive | $293,500 | 2026-08-26 | 2008 | 1,486 |
| 5515 Windsong Oak Dr | $339,400 | 2025-10-03 | 2020 | 1,749 |
| 5509 Windsong Oak Drive | $349,000 | 2025-05-01 | 2020 | 1,709 |
| 5905 Windsong Oak Drive | $330,000 | 2025-02-08 | 2014 | 2,084 |
| 5901 Windsong Oak Drive | $320,000 | 2025-01-30 | 2013 | 1,749 |
| 5527 Windsong Oak Drive | $305,000 | 2025-01-06 | 2010 | 1,557 |
| 6005 Windsong Oak Drive | $342,400 | 2024-12-23 | 2019 | 2,100 |
| 5635 Windsong Oak Drive | $365,000 | 2024-10-28 | 2020 | 1,704 |
| 5728 Windsong Oak Drive | $335,000 | 2024-09-18 | 2019 | 1,704 |
| 5916 Windsong Oak Drive | $305,000 | 2024-07-22 | 2011 | 1,727 |
| 5614 Windsong Oak Drive | $425,000 | 2024-06-20 | 2007 | 2,824 |
| 5929 Windsong Oak Drive | $310,000 | 2023-09-25 | 2013 | 1,956 |
| 5835 Windsong Oak Drive | $348,000 | 2023-09-21 | 2013 | 2,144 |
| 5528 Windsong Oak Drive | $375,000 | 2023-08-31 | 2019 | 2,103 |
| 5533 Windsong Oak Drive | $425,000 | 2023-06-15 | 2008 | 2,731 |
| 5800 Windsong Oak Drive | $369,900 | 2022-12-13 | 2007 | 2,619 |
| 5706 Windsong Oak Drive | $475,000 | 2022-08-22 | 2019 | 3,216 |
| 5748 Windsong Oak Drive | $365,500 | 2022-06-17 | 2006 | 2,238 |
| 5650 Windsong Oak Drive | $352,000 | 2021-12-29 | 2006 | 2,507 |
| 5732 Windsong Oak Drive | $345,000 | 2021-12-16 | 2019 | 2,100 |
Communities along Windsong Oak Drive
- Windsong At Leesburg · 63 homes on the street
- Windsong/Leesburg · 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 669 homes for sale in Leesburg, homes for sale in 34748.