Winter Park Road, Winter Park, FL
Everything we know about Winter Park Road 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.
29 homes sit on Winter Park Road in Winter Park, FL (ZIP 32789), built 1925–2024, a typical 1,680 sq ft with 3 bedrooms. 1 is for sale right now from $2,089,000. 3 closed in the last 12 months at a median of $892,500. Homes that sold since 2023 went for a median $717,500.
For sale on Winter Park Road now
Recent sales on Winter Park Road
| Address | Sold | Closed | Beds / baths | Sq ft |
|---|---|---|---|---|
| 2501 Winter Park Road | $1,650,000 | 2026-09-29 | 5 / 3.5 | 3,304 |
| 1900 Winter Park Road | $760,000 | 2026-08-26 | 4 / 2.0 | 1,511 |
| 1960 Winter Park Road | $892,500 | 2026-06-25 | 3 / 3.0 | 1,864 |
The homes on Winter Park Road
28 single-family, 1 condo/townhome/other. Built by decade: 1920s 3, 1940s 3, 1950s 11, 1960s 2, 1970s 2, 1980s 2, 2000s 1, 2010s 3, 2020s 2.
Last recorded sales (parcel record)
| Address | Sold | Date | Built | Sq ft |
|---|---|---|---|---|
| 2501 Winter Park Road | $1,650,000 | 2026-09-29 | 2014 | 3,304 |
| 1900 Winter Park Road | $760,000 | 2026-08-26 | 1947 | 1,511 |
| 1960 Winter Park Road | $892,500 | 2026-06-25 | 1948 | 1,864 |
| 2602 Winter Park Road | $675,000 | 2025-06-04 | 1975 | 1,966 |
| 2413 Winter Park Road | $3,270,500 | 2024-03-14 | 2024 | 4,905 |
| 2619 Winter Park Road | $600,000 | 2024-01-23 | 1926 | 3,130 |
| 1710 Winter Park Road | $669,000 | 2023-12-28 | 1952 | 1,556 |
| 1740 Winter Park Road | $640,000 | 2023-12-20 | 1950 | 1,451 |
| 2502 Winter Park Road | $406,000 | 2023-07-27 | 1950 | 1,330 |
| 1841 Winter Park Road | $772,000 | 2023-02-24 | 1948 | 2,452 |
| 2416 Winter Park Road | $685,000 | 2022-07-29 | 1928 | 1,680 |
| 2408 Winter Park Road | $465,000 | 2022-02-24 | 1987 | 1,291 |
| 2710 Winter Park Road | $355,000 | 2021-05-18 | 1957 | 1,328 |
| 2388 Winter Park Road | $1,250,000 | 2021-05-14 | 2021 | 3,034 |
| 1877 Winter Park Road | $586,000 | 2021-02-19 | 1950 | 1,900 |
| 2605 Winter Park Road | $620,000 | 2021-02-18 | 1981 | 2,365 |
| 2349 Winter Park Road | $450,000 | 2020-12-23 | 1967 | 1,453 |
| 2121 Winter Park Road | $445,000 | 2020-11-10 | 1950 | 1,453 |
| 1951 Winter Park Rd | $975,000 | 2020-03-31 | 2014 | 3,479 |
| 2606 Winter Park Road | $350,000 | 2019-06-28 | 1959 | 1,586 |
Communities along Winter Park Road
- Charmont · 11 homes on the street
- Parklando · 6 homes on the street
- Edgewood · 3 homes on the street
- Parklando · 2 homes on the street
- Parklando · 2 homes on the street
- Parklando · 2 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 32789.