Chestnut Avenue, Winter Park, FL
Everything we know about Chestnut 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.
44 homes sit on Chestnut Avenue in Winter Park, FL (ZIP 32789), built 1926–2024, a typical 2,180 sq ft with 3 bedrooms. 2 are for sale right now from $879,000 to $985,000. 4 closed in the last 12 months at a median of $1,445,500. Homes that sold since 2023 went for a median $1,095,000.
For sale on Chestnut Avenue now
Recent sales on Chestnut Avenue
| Address | Sold | Closed | Beds / baths | Sq ft |
|---|---|---|---|---|
| 1723 Chestnut Avenue | $1,201,000 | 2026-06-18 | 3 / 2.5 | 2,608 |
| 1630 Chestnut Avenue | $1,690,000 | 2026-03-06 | 3 / 4.5 | 3,164 |
| 1752 Chestnut Avenue | $1,875,000 | 2026-01-01 | 4 / 4.5 | 3,314 |
| 1450 Chestnut Avenue | $1,095,000 | 2025-12-01 | 3 / 3.5 | 1,942 |
The homes on Chestnut Avenue
43 single-family, 1 condo/townhome/other. Built by decade: 1920s 1, 1950s 10, 1960s 7, 1970s 7, 1980s 1, 1990s 2, 2000s 4, 2010s 4, 2020s 8.
Last recorded sales (parcel record)
| Address | Sold | Date | Built | Sq ft |
|---|---|---|---|---|
| 1723 Chestnut Avenue | $1,201,000 | 2026-06-18 | 1962 | 2,608 |
| 1630 Chestnut Avenue | $1,690,000 | 2026-03-06 | 2021 | 3,164 |
| 1752 Chestnut Avenue | $1,875,000 | 2026-01-01 | 2021 | 3,314 |
| 1450 Chestnut Avenue | $1,095,000 | 2025-12-01 | 2009 | 1,942 |
| 1711 Chestnut Avenue | $1,040,000 | 2025-10-03 | 1963 | 2,720 |
| 1610 Chestnut Avenue | $980,000 | 2025-08-28 | 1974 | 2,140 |
| 1541 Chestnut Avenue | $1,607,160 | 2025-08-01 | 2018 | 2,840 |
| 1511 Chestnut Avenue | $675,000 | 2025-07-10 | 1960 | 1,275 |
| 1585 Chestnut Avenue | $987,500 | 2025-06-10 | 1959 | 2,220 |
| 1601 Chestnut Avenue | $1,295,000 | 2025-04-22 | 2017 | 2,795 |
| 1691 Chestnut Avenue | $4,100,000 | 2025-04-18 | 2024 | 4,582 |
| 1506 Chestnut Ave. | $2,500,000 | 2025-02-28 | 2021 | 3,545 |
| 1762 Chestnut Avenue | $899,000 | 2024-12-27 | 1957 | 1,760 |
| 1580 Chestnut Avenue | $606,000 | 2024-10-17 | 1971 | 1,482 |
| 1771 Chestnut Avenue | $835,000 | 2024-04-09 | 1963 | 2,051 |
| 1742 Chestnut Avenue | $680,000 | 2024-01-30 | 1957 | 1,729 |
| 1425 Chestnut Ave. | $560,000 | 2023-10-30 | 1926 | 1,090 |
| 1340 Chestnut Avenue | $2,200,000 | 2023-09-19 | 1963 | 4,182 |
| 1772 Chestnut Avenue | $2,150,000 | 2023-08-18 | 2023 | 3,850 |
| 1640 Chestnut Avenue | $1,360,000 | 2022-06-27 | 2021 | 2,550 |
Communities along Chestnut Avenue
- Lake Knowles Terrace · 30 homes on the street
- Conwill Estates · 9 homes on the street
- Lake Knowles Terrace · 2 homes on the street
- Lake Knowles Terrace · 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 32789.