Carolina Avenue, Winter Park, FL
Everything we know about Carolina 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.
13 homes sit on Carolina Avenue in Winter Park, FL (ZIP 32789), built 1923–2023, a typical 1,723 sq ft with 3 bedrooms. 3 are for sale right now from $650,000 to $739,000. 5 closed in the last 12 months at a median of $725,000. Homes that sold since 2023 went for a median $1,325,000.
For sale on Carolina Avenue now
Recent sales on Carolina Avenue
| Address | Sold | Closed | Beds / baths | Sq ft |
|---|---|---|---|---|
| 300 Carolina Avenue #301 | $725,000 | 2026-08-07 | 2 / 2.0 | 1,305 |
| 433 Carolina Avenue | $1,395,000 | 2026-06-01 | 5 / 3.5 | 2,771 |
| 300 Carolina Avenue #207 | $400,000 | 2026-05-08 | 1 / 2.0 | 1,149 |
| 456 Carolina Avenue | $975,000 | 2026-03-25 | 3 / 3.0 | 1,615 |
| 300 Carolina Avenue #201 | $702,050 | 2026-01-23 | 2 / 2.0 | 1,305 |
The homes on Carolina Avenue
11 single-family, 2 condo/townhome/other. Built by decade: 1920s 3, 1980s 2, 2000s 5, 2010s 1, 2020s 2.
Last recorded sales (parcel record)
| Address | Sold | Date | Built | Sq ft |
|---|---|---|---|---|
| 433 Carolina Avenue | $1,395,000 | 2026-06-01 | 2018 | 2,771 |
| 456 Carolina Avenue | $975,000 | 2026-03-25 | 2004 | 1,615 |
| 422 Carolina Avenue | $1,255,000 | 2023-08-11 | 2004 | 2,351 |
| 521 Carolina Avenue | $1,734,500 | 2023-06-21 | 2023 | 2,449 |
| 467 Carolina Avenue | $1,125,000 | 2021-04-15 | 2020 | 2,710 |
| 453 Carolina Avenue | $655,000 | 2020-06-24 | 2004 | 1,723 |
| 518 Carolina Avenue | $530,000 | 2016-10-28 | 2004 | 1,914 |
| 405 Carolina Avenue | $250,000 | 2015-04-10 | 1923 | 1,004 |
| 506 Carolina Avenue | $110,000 | 2015-03-25 | 1926 | 1,386 |
| 466 Carolina Avenue | $445,000 | 2008-03-10 | 2006 | 2,166 |
| 440 Carolina Avenue | $300,000 | 2007-01-19 | 1927 | 694 |
| 250 Carolina Avenue | $235,000 | 2005-05-03 | 1981 | 1,153 |
| 300 Carolina Avenue | $300,000 | 2004-11-18 | 1982 | 1,311 |
Communities along Carolina Avenue
- Winter Park · 8 homes on the street
- Town Of Winter Park · 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.