Roxbury Road, Winter Park, FL
Everything we know about Roxbury 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.
32 homes sit on Roxbury Road in Winter Park, FL (ZIP 32789), built 1937–2023, a typical 1,537 sq ft with 3 bedrooms. 1 is for sale right now from $605,000. 2 closed in the last 12 months at a median of $505,000. Homes that sold since 2023 went for a median $412,500.
For sale on Roxbury Road now
Recent sales on Roxbury Road
| Address | Sold | Closed | Beds / baths | Sq ft |
|---|---|---|---|---|
| 2361 Roxbury Road | $540,000 | 2026-10-01 | 3 / 2.0 | 1,723 |
| 2381 Roxbury Road | $470,000 | 2025-12-23 | 3 / 2.0 | 1,785 |
The homes on Roxbury Road
32 single-family. Built by decade: 1930s 1, 1940s 6, 1950s 23, 2020s 2.
Last recorded sales (parcel record)
| Address | Sold | Date | Built | Sq ft |
|---|---|---|---|---|
| 2361 Roxbury Road | $540,000 | 2026-10-01 | 1951 | 1,723 |
| 2381 Roxbury Road | $470,000 | 2025-12-23 | 1949 | 1,785 |
| 2886 Roxbury Road | $316,000 | 2025-02-04 | 1954 | 1,162 |
| 2541 Roxbury Road | $375,000 | 2024-08-12 | 1951 | 1,210 |
| 2891 Roxbury Road | $400,000 | 2024-05-20 | 1955 | 1,477 |
| 2520 Roxbury Road | $320,000 | 2024-04-17 | 1945 | 847 |
| 2430 Roxbury Road | $969,000 | 2024-02-26 | 2023 | 3,110 |
| 2400 Roxbury Road | $997,500 | 2023-12-29 | 2023 | 3,110 |
| 2612 Roxbury Road | $425,000 | 2023-12-27 | 1957 | 2,472 |
| 2526 Roxbury Road | $300,000 | 2023-08-18 | 1950 | 1,276 |
| 2561 Roxbury Road | $305,000 | 2022-08-19 | 1951 | 890 |
| 2834 Roxbury Road | $355,000 | 2022-08-01 | 1955 | 1,332 |
| 2450 Roxbury Road | $265,000 | 2022-06-23 | 1947 | 1,068 |
| 2521 Roxbury Road | $335,000 | 2022-04-08 | 1951 | 1,220 |
| 2440 Roxbury Road | $350,000 | 2021-10-28 | 1947 | 1,721 |
| 2825 Roxbury Road | $265,000 | 2021-05-10 | 1955 | 1,261 |
| 2880 Roxbury Road | $283,000 | 2021-02-26 | 1954 | 1,348 |
| 2654 Roxbury Road | $170,000 | 2021-01-04 | 1947 | 625 |
| 2885 Roxbury Road | $310,000 | 2020-01-31 | 1955 | 1,511 |
| 2524 Roxbury Road | $453,100 | 2018-06-01 | 1952 | 3,346 |
Communities along Roxbury Road
- Glencoe · 14 homes on the street
- Glencoe · 7 homes on the street
- Fairbanks Shores · 7 homes on the street
- Glencoe · 1 homes on the street
- Fairbanks Shores · 1 homes on the street
- Glencoe · 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 402 homes for sale in Winter Park, homes for sale in 32789.