Trailwood Drive, Fleming Island, FL
Everything we know about Trailwood Drive in Fleming Island: 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.
61 homes sit on Trailwood Drive in Fleming Island, FL (ZIP 32003), built 2002–2003, a typical 1,820 sq ft with 3 bedrooms. Nothing is listed for sale on the street today. 2 closed in the last 12 months at a median of $388,050. Homes that sold since 2023 went for a median $375,000.
Recent sales on Trailwood Drive
| Address | Sold | Closed | Beds / baths | Sq ft |
|---|---|---|---|---|
| 2231 Trailwood Drive | $401,100 | 2026-02-13 | 3 / 2.0 | 1,669 |
| 2171 Trailwood Drive | $375,000 | 2025-12-10 | 3 / 2.0 | 1,726 |
The homes on Trailwood Drive
61 single-family. Built by decade: 2000s 61.
Last recorded sales (parcel record)
| Address | Sold | Date | Built | Sq ft |
|---|---|---|---|---|
| 2136 Trailwood Drive | $359,900 | 2026-05-22 | 2003 | 1,484 |
| 2231 Trailwood Drive | $401,100 | 2026-02-13 | 2003 | 1,669 |
| 2171 Trailwood Drive | $375,000 | 2025-12-10 | 2003 | 1,726 |
| 2250 Trailwood Drive | $385,000 | 2025-08-07 | 2003 | 1,711 |
| 2200 Trailwood Drive | $370,000 | 2025-06-27 | 2003 | 1,671 |
| 2147 Trailwood Drive | $374,900 | 2025-06-12 | 2003 | 1,893 |
| 2179 Trailwood Drive | $354,000 | 2025-05-15 | 2002 | 1,840 |
| 2203 Trailwood Drive | $403,650 | 2025-03-03 | 2002 | 2,099 |
| 2199 Trailwood Drive | $385,000 | 2024-12-05 | 2002 | 1,864 |
| 2219 Trailwood Drive | $470,000 | 2024-08-09 | 2003 | 2,095 |
| 2123 Trailwood Drive | $300,000 | 2023-12-01 | 2003 | 1,433 |
| 2218 Trailwood Drive | $329,000 | 2021-07-15 | 2003 | 1,731 |
| 2119 Trailwood Drive | $215,000 | 2020-12-09 | 2003 | 1,394 |
| 2275 Trailwood Drive | $330,000 | 2020-11-10 | 2003 | 2,884 |
| 2127 Trailwood Drive | $230,000 | 2020-09-25 | 2003 | 1,432 |
| 2139 Trailwood Drive | $250,000 | 2020-07-30 | 2003 | 1,669 |
| 2238 Trailwood Drive | $250,000 | 2020-03-30 | 2003 | 1,776 |
| 2144 Trailwood Drive | $260,000 | 2020-01-31 | 2003 | 2,123 |
| 2167 Trailwood Drive | $237,000 | 2018-05-07 | 2003 | 1,867 |
| 2235 Trailwood Drive | $181,084 | 2017-11-08 | 2003 | 1,820 |
Communities along Trailwood Drive
- Pine Lake · 29 homes on the street
- Eagle Harbor · 23 homes on the street
- Pine Lake · 9 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 121 homes for sale in Fleming Island, homes for sale in 32003.