Highland Woods Drive, Dunedin, FL
Everything we know about Highland Woods Drive in Dunedin: 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.
25 homes sit on Highland Woods Drive in Dunedin, FL (ZIP 34698), built 2002–2003, a typical 3,247 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 $810,000. Homes that sold since 2023 went for a median $836,000.
Recent sales on Highland Woods Drive
| Address | Sold | Closed | Beds / baths | Sq ft |
|---|---|---|---|---|
| 2206 Highland Woods Drive | $805,000 | 2026-06-02 | 4 / 3.0 | 2,560 |
| 2281 Highland Woods Drive | $810,000 | 2026-01-21 | 4 / 3.5 | 3,491 |
| 2258 Highland Woods Drive | $900,000 | 2026-01-16 | 4 / 3.5 | 3,543 |
The homes on Highland Woods Drive
25 single-family. Built by decade: 2000s 25.
Last recorded sales (parcel record)
| Address | Sold | Date | Built | Sq ft |
|---|---|---|---|---|
| 2206 Highland Woods Drive | $805,000 | 2026-06-02 | 2002 | 2,560 |
| 2281 Highland Woods Drive | $810,000 | 2026-01-21 | 2003 | 3,491 |
| 2258 Highland Woods Drive | $900,000 | 2026-01-16 | 2002 | 3,543 |
| 2278 Highland Woods Drive | $760,000 | 2024-10-23 | 2003 | 3,516 |
| 2274 Highland Woods Drive | $862,000 | 2024-07-19 | 2002 | 3,611 |
| 2254 Highland Woods Drive | $900,000 | 2024-03-29 | 2003 | 3,282 |
| 2273 Highland Woods Drive | $900,000 | 2022-06-17 | 2002 | 3,132 |
| 2266 Highland Woods Drive | $925,000 | 2022-06-15 | 2003 | 3,533 |
| 2255 Highland Woods Drive | $789,000 | 2022-03-25 | 2003 | 3,335 |
| 2217 Highland Woods Drive | $840,000 | 2022-03-04 | 2003 | 3,150 |
| 2249 Highland Woods Drive | $700,000 | 2021-08-31 | 2002 | 2,807 |
| 2205 Highland Woods Drive | $734,000 | 2021-07-08 | 2003 | 3,175 |
| 2214 Highland Woods Drive | $595,000 | 2021-07-08 | 2002 | 2,315 |
| 2286 Highland Woods Drive | $690,000 | 2021-05-25 | 2003 | 3,486 |
| 2282 Highland Woods Drive | $490,000 | 2020-09-11 | 2003 | 2,621 |
| 2226 Highland Woods Drive | $440,000 | 2019-06-25 | 2003 | 2,909 |
| 2290 Highland Woods Drive | $529,000 | 2019-03-29 | 2003 | 3,487 |
| 2237 Highland Woods Drive | $490,000 | 2018-07-24 | 2002 | 3,166 |
| 2209 Highland Woods Drive | $445,000 | 2017-03-01 | 2003 | 3,130 |
| 2270 Highland Woods Drive | $405,000 | 2013-07-26 | 2003 | 3,510 |
Communities along Highland Woods Drive
- Highland Woods · 23 homes on the street
- Highland Woods · 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 15, 2026. Listings appear courtesy of the listing brokerage under IDX rules; information deemed reliable but not guaranteed. See also all 284 homes for sale in Dunedin, homes for sale in 34698.