Leeward Island Drive, St. Augustine, FL
Everything we know about Leeward Island Drive in St. Augustine: 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.
39 homes sit on Leeward Island Drive in St. Augustine, FL (ZIP 32080, 32095), built 2005–2020, a typical 1,388 sq ft with 3 bedrooms. Nothing is listed for sale on the street today. 5 closed in the last 12 months at a median of $415,000. Homes that sold since 2023 went for a median $431,000.
Recent sales on Leeward Island Drive
| Address | Sold | Closed | Beds / baths | Sq ft |
|---|---|---|---|---|
| 189 Leeward Island Drive | $390,000 | 2026-05-21 | 3 / 2.5 | 1,789 |
| 267 Leeward Island Drive | $429,500 | 2026-02-11 | 3 / 2.0 | 1,388 |
| 267 Leeward Island Drive | $429,500 | 2026-02-11 | 3 / 2.0 | 1,388 |
| 165 Leeward Island Drive | $415,000 | 2025-10-17 | 4 / 2.5 | 1,805 |
| 165 Leeward Island Drive | $415,000 | 2025-10-17 | 4 / 2.5 | 1,805 |
The homes on Leeward Island Drive
2 single-family, 37 condo/townhome/other. Built by decade: 2000s 1, 2010s 31, 2020s 7.
Last recorded sales (parcel record)
| Address | Sold | Date | Built | Sq ft |
|---|---|---|---|---|
| 189 Leeward Island Drive | $390,000 | 2026-05-21 | 2019 | 1,789 |
| 267 Leeward Island Drive | $429,500 | 2026-02-11 | 2019 | 1,388 |
| 165 Leeward Island Drive | $415,000 | 2025-10-17 | 2019 | 1,805 |
| 23 Leeward Island Drive | $399,900 | 2025-03-31 | 2019 | 1,388 |
| 39 Leeward Island Drive | $460,000 | 2024-08-20 | 2019 | 1,388 |
| 116 Leeward Island Drive | $457,500 | 2024-07-26 | 2019 | 1,388 |
| 36 Leeward Island Drive | $462,500 | 2023-09-22 | 2019 | 1,789 |
| 100 Leeward Island Drive | $432,500 | 2023-03-02 | 2019 | 1,388 |
| 53 Leeward Island Drive | $425,000 | 2022-08-02 | 2019 | 1,789 |
| 47 Leeward Island Drive | $450,000 | 2022-07-14 | 2019 | 1,388 |
| 24 Leeward Island Drive | $436,000 | 2022-04-08 | 2019 | 1,388 |
| 213 Leeward Island Drive | $425,000 | 2022-02-04 | 2019 | 1,789 |
| 60 Leeward Island Drive | $397,500 | 2021-11-12 | 2019 | 1,789 |
| 133 Leeward Island Drive | $325,000 | 2021-06-02 | 2019 | 1,388 |
| 101 Leeward Island Drive | $309,652 | 2021-01-05 | 2020 | 1,789 |
| 121 Leeward Island Drive | $308,296 | 2020-12-30 | 2020 | 1,789 |
| 84 Leeward Island Drive | $323,535 | 2020-12-29 | 2020 | 1,789 |
| 117 Leeward Island Drive | $299,752 | 2020-11-24 | 2020 | 1,388 |
| 30 Leeward Island Drive | $324,990 | 2020-11-23 | 2019 | 2,081 |
| 77 Leeward Island Drive | $294,990 | 2020-10-23 | 2020 | 1,789 |
Communities along Leeward Island Drive
- Antigua Townhomes · 30 homes on the street
- Antigua · 8 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 15, 2026. Listings appear courtesy of the listing brokerage under IDX rules; information deemed reliable but not guaranteed. See also all 1,076 homes for sale in St. Augustine, homes for sale in 32080, homes for sale in 32095.