Olive Hill Drive, Winter Garden, FL
Everything we know about Olive Hill Drive in Winter Garden: 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.
26 homes sit on Olive Hill Drive in Winter Garden, FL (ZIP 34787), built 2018–2020, a typical 2,412 sq ft with 3 bedrooms. 2 are for sale right now from $560,000 to $564,900. 1 closed in the last 12 months at a median of $599,900. Homes that sold since 2023 went for a median $599,900.
For sale on Olive Hill Drive now
Recent sales on Olive Hill Drive
| Address | Sold | Closed | Beds / baths | Sq ft |
|---|---|---|---|---|
| 16467 Olive Hill Drive | $599,900 | 2026-05-22 | 3 / 2.5 | 2,355 |
The homes on Olive Hill Drive
20 single-family, 6 condo/townhome/other. Built by decade: 2010s 20, 2020s 6.
Last recorded sales (parcel record)
| Address | Sold | Date | Built | Sq ft |
|---|---|---|---|---|
| 16467 Olive Hill Drive | $599,900 | 2026-05-22 | 2019 | 2,355 |
| 16526 Olive Hill Drive | $565,000 | 2025-11-17 | 2019 | 2,008 |
| 16694 Olive Hill Drive | $807,000 | 2025-06-03 | 2019 | 2,862 |
| 16682 Olive Hill Drive | $655,000 | 2025-03-20 | 2019 | 2,224 |
| 16556 Olive Hill Drive | $1,140,000 | 2025-02-20 | 2019 | 3,752 |
| 16425 Olive Hill Drive | $559,000 | 2024-08-01 | 2019 | 2,008 |
| 16508 Olive Hill Drive | $565,000 | 2024-07-11 | 2019 | 2,008 |
| 16413 Olive Hill Drive | $565,000 | 2024-06-28 | 2020 | 2,072 |
| 16406 Olive Hill Drive | $832,000 | 2024-06-04 | 2019 | 2,470 |
| 16765 Olive Hill Drive | $480,000 | 2024-02-29 | 2020 | 1,676 |
| 16741 Olive Hill Drive | $633,000 | 2023-10-20 | 2020 | 2,608 |
| 16472 Olive Hill Drive | $615,000 | 2021-12-13 | 2019 | 3,083 |
| 16431 Olive Hill Drive | $436,500 | 2021-07-01 | 2019 | 2,008 |
| 16430 Olive Hill Drive | $544,900 | 2021-04-26 | 2019 | 3,093 |
| 16735 Olive Hill Drive Lot 220 | $398,809 | 2020-11-30 | 2020 | 2,608 |
| 16454 Olive Hill Drive | $370,000 | 2020-11-25 | 2019 | 2,020 |
| 16783 Olive Hill Drive | $410,892 | 2020-03-30 | 2019 | 2,027 |
| 16789 Olive Hill Drive | $410,892 | 2020-02-27 | 2020 | 2,608 |
| 16771 Olive Hill Drive | $389,812 | 2020-02-26 | 2020 | 2,355 |
| 16587 Olive Hill Drive | $446,194 | 2019-12-10 | 2019 | 3,372 |
Communities along Olive Hill Drive
- hawksmoor · 10 homes on the street
- hawksmoor · 5 homes on the street
- hawksmoor · 5 homes on the street
- hawksmoor · 1 homes on the street
- hawksmoor · 1 homes on the street
- hawksmoor · 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 14, 2026. Listings appear courtesy of the listing brokerage under IDX rules; information deemed reliable but not guaranteed. See also all 710 homes for sale in Winter Garden, homes for sale in 34787.