Sunset Drive, Winter Park, FL

Everything we know about Sunset 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.

34 homes sit on Sunset Drive in Winter Park, FL (ZIP 32789), built 1925–2022, a typical 2,716 sq ft with 4 bedrooms. 1 is for sale right now from $2,549,000. 1 closed in the last 12 months at a median of $1,770,000. Homes that sold since 2023 went for a median $1,080,000.

For sale on Sunset Drive now

1823 Sunset Drive, home for sale on Sunset Drive
$2,549,000
5 bd · 4.5 ba · 3,479 sq ft · built 2026
1823 Sunset Drive
Listing courtesy of ONE LUXURY INTERNATIONAL LLC

Recent sales on Sunset Drive

AddressSoldClosedBeds / bathsSq ft
1230 Sunset Drive$1,770,0002026-10-094 / 3.53,250

The homes on Sunset Drive

34 single-family. Built by decade: 1920s 1, 1930s 2, 1940s 2, 1950s 4, 1970s 2, 1990s 9, 2000s 8, 2010s 4, 2020s 2.

Last recorded sales (parcel record)

AddressSoldDateBuiltSq ft
1230 Sunset Drive$1,770,0002026-10-0920063,250
1409 Sunset Drive$530,0002025-10-0219301,107
1421 Sunset Drive$825,0002025-09-1519771,672
1823 Sunset Drive$800,0002025-07-1819402,414
1571 Sunset Drive$1,446,0002024-11-0420152,700
1531 Sunset Drive$1,200,0002023-10-2519922,619
1572 Sunset Drive$1,080,0002023-07-2120222,626
1336 Sunset Drive$1,037,5002022-10-0419502,732
1562 Sunset Drive$635,0002021-11-1519251,628
1760 Sunset Drive$1,805,0002021-07-3020064,084
1144 Sunset Drive$1,650,0002021-06-1820084,777
1370 Sunset Drive$917,5002021-06-0819983,606
1324 Sunset Drive$875,0002020-10-1519913,280
1535 Sunset Drive$1,050,0002020-07-2020132,822
1315 Sunset Drive$870,0002020-06-1019953,058
1133 Sunset Drive$1,240,0002020-04-1020202,686
1450 Sunset Drive$560,0002020-01-1419912,486
1900 Sunset Drive$1,150,0002019-10-2520182,850
1310 Sunset Drive$660,0002018-04-2020052,233
1333 Sunset Drive$680,0002018-03-0119953,352

Communities along Sunset Drive

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.

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Common questions

How many homes are on Sunset Drive in Winter Park?

34 homes in the parcel and MLS record, built between 1925 and 2022.

Are there homes for sale on Sunset Drive?

1 listed right now, from $2,549,000.

What do homes on Sunset Drive sell for?

The median closing over the last 12 months was $1,770,000.