Trailing Pines Way, Fleming Island, FL
Everything we know about Trailing Pines Way 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.
27 homes sit on Trailing Pines Way in Fleming Island, FL (ZIP 32003), built 2002–2003, a typical 2,082 sq ft with 4 bedrooms. Nothing is listed for sale on the street today. 3 closed in the last 12 months at a median of $420,000. Homes that sold since 2023 went for a median $439,000.
Recent sales on Trailing Pines Way
| Address | Sold | Closed | Beds / baths | Sq ft |
|---|---|---|---|---|
| 2053 Trailing Pines Way | $450,000 | 2026-08-14 | 4 / 3.0 | 2,302 |
| 2028 Trailing Pines Way | $420,000 | 2026-07-30 | 3 / 2.0 | 2,055 |
| 2028 Trailing Pines Way | $420,000 | 2026-07-30 | 3 / 2.0 | 2,055 |
The homes on Trailing Pines Way
27 single-family. Built by decade: 2000s 27.
Last recorded sales (parcel record)
| Address | Sold | Date | Built | Sq ft |
|---|---|---|---|---|
| 2053 Trailing Pines Way | $450,000 | 2026-08-14 | 2003 | 2,302 |
| 2028 Trailing Pines Way | $420,000 | 2026-07-30 | 2003 | 2,055 |
| 2065 Trailing Pines Way | $439,000 | 2026-05-29 | 2002 | 2,082 |
| 2061 Trailing Pines Way | $445,000 | 2025-06-11 | 2003 | 2,302 |
| 2040 Trailing Pines Way | $405,000 | 2025-04-18 | 2003 | 2,084 |
| 2037 Trailing Pines Way | $465,000 | 2024-08-19 | 2002 | 2,406 |
| 2036 Trailing Pines Way | $390,000 | 2023-12-08 | 2003 | 2,065 |
| 2025 Trailing Pines Way | $599,000 | 2023-12-07 | 2003 | 2,650 |
| 2075 Trailing Pines Way | $360,000 | 2023-06-26 | 2003 | 1,510 |
| 2057 Trailing Pines Way | $280,000 | 2021-06-03 | 2003 | 2,113 |
| 2079 Trailing Pines Way | $237,500 | 2020-08-28 | 2003 | 1,663 |
| 2020 Trailing Pines Way | $270,000 | 2020-06-29 | 2003 | 1,731 |
| 2045 Trailing Pines Way | $270,000 | 2020-06-29 | 2003 | 1,820 |
| 2032 Trailing Pines Way | $275,000 | 2018-12-05 | 2003 | 2,884 |
| 2024 Trailing Pines Way | $317,000 | 2018-02-01 | 2003 | 2,770 |
| 2048 Trailing Pines Way | $190,500 | 2016-08-17 | 2003 | 1,669 |
| 2044 Trailing Pines Way | $215,000 | 2016-07-18 | 2003 | 1,893 |
| 2080 Trailing Pines Way | $240,000 | 2016-03-28 | 2003 | 2,836 |
| 2041 Trailing Pines Way | $184,000 | 2012-11-02 | 2002 | 2,099 |
| 2056 Trailing Pines Way | $179,500 | 2005-03-29 | 2003 | 1,438 |
Communities along Trailing Pines Way
- Eagle Harbor · 14 homes on the street
- Pine Lake · 9 homes on the street
- Pine Lake · 4 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.