Whitehall Drive, Winter Park, FL
Everything we know about Whitehall Drive in Winter Park: 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 Whitehall Drive in Winter Park, FL (ZIP 32792, 32789), built 1958–2026, a typical 1,845 sq ft with 3 bedrooms. 1 is for sale right now from $2,995,000. 1 closed in the last 12 months at a median of $635,000. Homes that sold since 2023 went for a median $642,500.
For sale on Whitehall Drive now
Recent sales on Whitehall Drive
| Address | Sold | Closed | Beds / baths | Sq ft |
|---|---|---|---|---|
| 2030 Whitehall Drive | $635,000 | 2026-08-31 | 4 / 2.5 | 1,874 |
The homes on Whitehall Drive
25 single-family. Built by decade: 1950s 4, 1960s 20, 2020s 1.
Last recorded sales (parcel record)
| Address | Sold | Date | Built | Sq ft |
|---|---|---|---|---|
| 2030 Whitehall Drive | $635,000 | 2026-08-31 | 1964 | 1,874 |
| 2138 Whitehall Drive | $500,000 | 2025-07-25 | 1964 | 1,752 |
| 2178 Whitehall Drive | $738,000 | 2025-05-09 | 1964 | 2,360 |
| 2258 Whitehall Drive | $530,000 | 2024-05-24 | 1963 | 1,620 |
| 2358 Whitehall Drive | $650,000 | 2024-05-09 | 1967 | 2,407 |
| 1936 Whitehall Drive | $679,900 | 2023-08-30 | 1963 | 1,769 |
| 2000 Whitehall Drive | $664,000 | 2022-11-09 | 1963 | 1,820 |
| 2158 Whitehall Drive | $530,000 | 2022-09-16 | 1964 | 1,784 |
| 2318 Whitehall Drive | $585,000 | 2021-09-14 | 1963 | 2,109 |
| 2117 Whitehall Drive | $595,000 | 2021-06-16 | 1963 | 1,816 |
| 1849 Whitehall Drive | $453,500 | 2020-10-30 | 1959 | 1,617 |
| 2308 Whitehall Drive | $395,000 | 2020-09-04 | 1963 | 1,637 |
| 2118 Whitehall Drive | $370,000 | 2020-08-31 | 1964 | 1,889 |
| 1832 Whitehall Drive | $599,000 | 2019-04-18 | 1958 | 3,050 |
| 2128 Whitehall Drive | $385,000 | 2018-10-05 | 1964 | 1,808 |
| 2139 Whitehall Drive | $348,250 | 2017-07-18 | 1963 | 1,838 |
| 2219 Whitehall Drive | $390,000 | 2017-06-15 | 1963 | 2,405 |
| 1850 Whitehall Drive | $310,000 | 2015-04-02 | 1958 | 1,670 |
| 1906 Whitehall Drive | $314,900 | 2014-08-29 | 1962 | 2,157 |
| 2179 Whitehall Drive | $375,000 | 2014-04-25 | 1963 | 2,254 |
Communities along Whitehall Drive
- Brookshire Heights · 5 homes on the street
- Kenilworth Shores · 4 homes on the street
- Kenilworth Shores · 4 homes on the street
- Kenilworth Shores · 3 homes on the street
- Kenilworth Shores · 2 homes on the street
- Kenilworth Shores · 1 homes on the street
- Brookshire Heights · 1 homes on the street
- Kenilworth Shores · 1 homes on the street
- Brookshire Heights · 1 homes on the street
- Brookshire Heights · 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 350 homes for sale in Winter Park, homes for sale in 32792, homes for sale in 32789.