Gaineswood Drive, Milton, FL
Everything we know about Gaineswood Drive in Milton: 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.
64 homes sit on Gaineswood Drive in Milton, FL (ZIP 32583), built 2019–2026, a typical 1,900 sq ft with 4 bedrooms. 3 are for sale right now from $324,900 to $334,900. 6 closed in the last 12 months at a median of $353,400. Homes that sold since 2023 went for a median $321,400.
For sale on Gaineswood Drive now
Recent sales on Gaineswood Drive
| Address | Sold | Closed | Beds / baths | Sq ft |
|---|---|---|---|---|
| 4969 Gaineswood Dr | $321,900 | 2026-09-30 | 4 / 2.0 | 1,856 |
| 4958 Gaineswood Dr | $319,900 | 2026-09-28 | 4 / 2.0 | 1,856 |
| 4975 Gaineswood Dr | $384,900 | 2026-09-18 | 4 / 3.0 | 1,968 |
| 5126 Gaineswood Dr | $314,500 | 2026-09-16 | 4 / 2.0 | 1,830 |
| 4982 Gaineswood Dr | $437,900 | 2026-08-28 | 4 / 3.5 | 2,831 |
| 4957 Gaineswood Dr | $389,900 | 2026-08-25 | 5 / 3.0 | 2,595 |
The homes on Gaineswood Drive
64 single-family. Built by decade: 2010s 3, 2020s 61.
Last recorded sales (parcel record)
| Address | Sold | Date | Built | Sq ft |
|---|---|---|---|---|
| 4969 Gaineswood Drive | $321,900 | 2026-09-30 | 2026 | 1,856 |
| 4958 Gaineswood Drive | $319,900 | 2026-09-28 | 2026 | 1,856 |
| 4975 Gaineswood Drive | $384,900 | 2026-09-18 | 2026 | 1,968 |
| 5126 Gaineswood Drive | $314,500 | 2026-09-16 | 2023 | 1,830 |
| 4982 Gaineswood Drive | $437,900 | 2026-08-28 | 2025 | 2,831 |
| 4957 Gaineswood Drive | $389,900 | 2026-08-25 | 2026 | 2,595 |
| 5030 Gaineswood Drive | $472,900 | 2026-08-14 | 2026 | 3,129 |
| 4951 Gaineswood Drive | $325,900 | 2026-08-13 | 2026 | 1,856 |
| 5150 Gaineswood Drive | $312,000 | 2026-07-23 | 2023 | 1,846 |
| 4952 Gaineswood Drive | $329,900 | 2026-07-17 | 2026 | 1,856 |
| 5042 Gaineswood Drive | $469,900 | 2026-06-29 | 2026 | 3,129 |
| 5012 Gaineswood Drive | $404,900 | 2026-06-26 | 2026 | 2,377 |
| 5196 Gaineswood Drive | $440,000 | 2026-05-28 | 2021 | 2,626 |
| 5000 Gaineswood Drive | $460,000 | 2026-05-27 | 2026 | 3,129 |
| 5261 Gaineswood Drive | $370,000 | 2025-11-21 | 2020 | 2,371 |
| 5253 Gaineswood Drive | $430,000 | 2025-09-12 | 2020 | 2,669 |
| 5274 Gaineswood Dr | $515,000 | 2024-11-05 | 2020 | 2,561 |
| 5174 Gaineswood Dr | $311,900 | 2024-10-02 | 2021 | 1,924 |
| 5220 Gaineswood Dr | $399,000 | 2024-08-26 | 2021 | 2,630 |
| 5202 Gaineswood Dr | $327,000 | 2024-07-23 | 2021 | 1,924 |
Communities along Gaineswood Drive
- Plantation Woods · 64 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 402 homes for sale in Milton, homes for sale in 32583.