Howard Drive, Winter Park, FL
Everything we know about Howard Drive 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.
35 homes sit on Howard Drive in Winter Park, FL (ZIP 32789), built 1952–2019, a typical 1,955 sq ft with 3 bedrooms. 2 are for sale right now from $2,295,000 to $3,195,000. Homes that sold since 2023 went for a median $825,000.
For sale on Howard Drive now
The homes on Howard Drive
35 single-family. Built by decade: 1950s 30, 1960s 2, 1980s 1, 2000s 1, 2010s 1.
Last recorded sales (parcel record)
| Address | Sold | Date | Built | Sq ft |
|---|---|---|---|---|
| 2208 Howard Drive | $845,000 | 2026-06-12 | 1957 | 2,155 |
| 2119 Howard Drive | $841,500 | 2026-05-22 | 1962 | 2,479 |
| 2258 Howard Drive | $740,000 | 2024-11-11 | 1953 | 2,747 |
| 2217 Howard Drive | $1,025,000 | 2024-09-13 | 1957 | 2,387 |
| 2228 Howard Drive | $525,900 | 2024-02-20 | 1952 | 1,816 |
| 2227 Howard Drive | $825,000 | 2023-07-14 | 1958 | 2,196 |
| 2230 Howard Drive | $635,000 | 2023-03-22 | 1952 | 1,574 |
| 2012 Howard Drive | $1,031,000 | 2022-12-21 | 1958 | 2,344 |
| 2237 Howard Drive | $717,000 | 2022-03-25 | 1956 | 2,008 |
| 2257 Howard Drive | $500,000 | 2022-02-24 | 1954 | 1,925 |
| 2266 Howard Drive | $410,000 | 2021-09-08 | 1953 | 1,290 |
| 2244 Howard Drive | $527,500 | 2021-07-28 | 1953 | 1,955 |
| 2004 Howard Drive | $625,000 | 2021-03-26 | 1958 | 1,866 |
| 2011 Howard Drive | $464,375 | 2020-11-17 | 1957 | 1,554 |
| 2240 Howard Drive | $725,000 | 2020-11-03 | 2019 | 2,853 |
| 2126 Howard Drive | $595,000 | 2019-10-18 | 1957 | 2,024 |
| 2221 Howard Drive | $785,000 | 2019-02-15 | 1980 | 3,908 |
| 2231 Howard Drive | $639,000 | 2016-12-21 | 1956 | 1,838 |
| 2252 Howard Drive | $350,000 | 2016-06-17 | 1952 | 1,406 |
| 2268 Howard Drive | $228,000 | 2016-04-29 | 1953 | 1,586 |
Communities along Howard Drive
- Lake Forest Park · 11 homes on the street
- Northwood Terrace · 3 homes on the street
- Northwood Terrace · 1 homes on the street
- Orangewood 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.