Sir Churchill Drive, Leesburg, FL
Everything we know about Sir Churchill 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.
53 homes sit on Sir Churchill Drive in Leesburg, FL (ZIP 34748), built 2001–2010, a typical 1,914 sq ft with 3 bedrooms. 1 is for sale right now from $389,999. 6 closed in the last 12 months at a median of $336,500. Homes that sold since 2023 went for a median $329,900.
For sale on Sir Churchill Drive now
Recent sales on Sir Churchill Drive
| Address | Sold | Closed | Beds / baths | Sq ft |
|---|---|---|---|---|
| 5401 Sir Churchill Drive | $390,000 | 2026-08-13 | 3 / 3.0 | 2,131 |
| 5524 Sir Churchill Drive | $333,000 | 2026-07-29 | 3 / 2.0 | 1,901 |
| 5433 Sir Churchill Drive | $250,000 | 2026-04-20 | 3 / 2.0 | 1,995 |
| 5421 Sir Churchill Drive | $384,000 | 2026-04-17 | 3 / 2.0 | 1,901 |
| 5543 Sir Churchill Drive | $340,000 | 2026-01-23 | 3 / 2.0 | 1,875 |
| 5535 Sir Churchill Drive | $279,900 | 2025-11-04 | 3 / 2.0 | 1,522 |
The homes on Sir Churchill Drive
53 single-family. Built by decade: 2000s 52, 2010s 1.
Last recorded sales (parcel record)
| Address | Sold | Date | Built | Sq ft |
|---|---|---|---|---|
| 5401 Sir Churchill Drive | $390,000 | 2026-08-13 | 2005 | 2,131 |
| 5524 Sir Churchill Drive | $333,000 | 2026-07-29 | 2006 | 1,901 |
| 5429 Sir Churchill Drive | $415,000 | 2026-07-24 | 2004 | 2,230 |
| 5433 Sir Churchill Drive | $250,000 | 2026-04-20 | 2006 | 1,995 |
| 5421 Sir Churchill Drive | $384,000 | 2026-04-17 | 2006 | 1,901 |
| 5430 Sir Churchill Drive | $287,000 | 2026-02-14 | 2001 | 1,986 |
| 5543 Sir Churchill Drive | $340,000 | 2026-01-23 | 2003 | 1,875 |
| 5644 Sir Churchill Drive | $374,999 | 2026-01-06 | 2006 | 1,977 |
| 5457 Sir Churchill Drive | $385,000 | 2025-12-18 | 2006 | 2,013 |
| 5454 Sir Churchill Drive | $275,000 | 2025-12-05 | 2004 | 1,647 |
| 5535 Sir Churchill Drive | $279,900 | 2025-11-04 | 2004 | 1,522 |
| 5622 Sir Churchill Drive | $258,000 | 2025-05-10 | 2005 | 1,202 |
| 5409 Sir Churchill Drive | $329,900 | 2024-11-01 | 2005 | 1,619 |
| 5446 Sir Churchill Drive | $320,000 | 2024-07-15 | 2001 | 1,996 |
| 5607 Sir Churchill Drive | $425,000 | 2024-04-26 | 2003 | 2,312 |
| 5425 Sir Churchill Drive | $315,000 | 2023-08-17 | 2004 | 1,411 |
| 5621 Sir Churchill Drive | $280,000 | 2023-02-28 | 2004 | 1,460 |
| 5640 Sir Churchill Drive | $320,000 | 2022-12-28 | 2004 | 1,712 |
| 5441 Sir Churchill Drive | $427,500 | 2022-10-28 | 2004 | 2,007 |
| 5316 Sir Churchill Drive | $245,000 | 2021-09-01 | 2002 | 1,425 |
Communities along Sir Churchill Drive
- Royal Highlands · 37 homes on the street
- Royal Highlands · 10 homes on the street
- Royal Highlands · 3 homes on the street
- Royal Highlands · 2 homes on the street
- Royal Highlands · 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 14, 2026. Listings appear courtesy of the listing brokerage under IDX rules; information deemed reliable but not guaranteed. See also all 637 homes for sale in Leesburg, homes for sale in 34748.