Westchester Avenue, Winter Park, FL
Everything we know about Westchester Avenue 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.
27 homes sit on Westchester Avenue in Winter Park, FL (ZIP 32789), built 1925–2010, a typical 2,102 sq ft with 3 bedrooms. 1 is for sale right now from $524,900. 1 closed in the last 12 months at a median of $1,125,000. Homes that sold since 2023 went for a median $830,000.
For sale on Westchester Avenue now
Recent sales on Westchester Avenue
| Address | Sold | Closed | Beds / baths | Sq ft |
|---|---|---|---|---|
| 1651 Westchester Avenue | $1,125,000 | 2026-06-23 | 3 / 2.5 | 2,426 |
The homes on Westchester Avenue
27 single-family. Built by decade: 1920s 4, 1930s 4, 1940s 8, 1950s 6, 1960s 2, 1990s 2, 2010s 1.
Last recorded sales (parcel record)
| Address | Sold | Date | Built | Sq ft |
|---|---|---|---|---|
| 1651 Westchester Avenue | $1,125,000 | 2026-06-23 | 1938 | 2,426 |
| 1494 Westchester Avenue | $540,000 | 2024-12-31 | 1956 | 1,740 |
| 1423 Westchester Avenue | $845,000 | 2024-11-04 | 1935 | 1,700 |
| 1501 Westchester Avenue | $750,000 | 2024-08-22 | 1966 | 2,126 |
| 1714 Westchester Avenue | $875,000 | 2023-11-28 | 1940 | 2,114 |
| 1741 Westchester Avenue | $575,000 | 2023-09-11 | 1964 | 1,434 |
| 1721 Westchester Avenue | $830,000 | 2023-01-31 | 1991 | 3,215 |
| 1710 Westchester Avenue | $505,000 | 2022-06-15 | 1940 | 1,619 |
| 1620 Westchester Avenue | $900,000 | 2021-12-17 | 2010 | 3,915 |
| 1415 Westchester Avenue | $940,000 | 2021-12-16 | 1925 | 3,427 |
| 1485 Westchester Avenue | $650,000 | 2021-06-08 | 1991 | 2,031 |
| 1470 Westchester Avenue | $1,020,000 | 2021-02-22 | 1946 | 4,077 |
| 1410 Westchester Avenue | $330,000 | 2019-12-31 | 1950 | 1,469 |
| 1455 Westchester Avenue | $840,000 | 2019-07-19 | 1936 | 2,704 |
| 1420 Westchester Avenue | $400,000 | 2019-02-22 | 1950 | 1,860 |
| 1329 Westchester Avenue | $420,000 | 2018-08-17 | 1946 | 2,081 |
| 1517 Westchester Avenue | $750,000 | 2018-07-30 | 1925 | 3,017 |
| 1493 Westchester Avenue | $485,000 | 2018-04-30 | 1945 | 2,106 |
| 1482 Westchester Avenue | $879,000 | 2017-10-06 | 1927 | 3,586 |
| 1353 Westchester Avenue | $262,000 | 2017-09-28 | 1949 | 1,266 |
Communities along Westchester Avenue
- Orwin Manor Westminster · 19 homes on the street
- Orwin Manor Westminster · 1 homes on the street
- Orwin Manor Westminster · 1 homes on the street
- Orwin Manor Westminster · 1 homes on the street
- Orwin Manor Westminster · 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.