20 Days on Market
House for Sale
$4,950,000
4 bd · 7 ba · 5,550 sqft
Bedrooms
Bathrooms
Winter Park Homes for Sale under $5M
301 listings
Newly Listed
House for Sale
$4,900,000
5 bd · 6 ba · 4,961 sqft
1180 VIA LUGANO, WINTER PARK, FL 32789
8 Days on Market
House for Sale
$4,750,000
5 bd · 6 ba · 5,211 sqft
1525 GRANVILLE DRIVE, WINTER PARK, FL 32789
108 Days on Market
House for Sale
$4,285,000
4 bd · 6 ba · 4,066 sqft
1441 CARDINAL COURT, WINTER PARK, FL 32789
25 Days on Market
House for Sale
$4,250,000
4 bd · 6 ba · 4,431 sqft
229 ALEXANDER PLACE, WINTER PARK, FL 32789
406 Days on Market
House for Sale
$3,975,000
4 bd · 6 ba · 3,850 sqft
1150 VIA SALERNO, WINTER PARK, FL 32789
8 Days on Market
Townhome for Sale
$3,895,000
3 bd · 5 ba · 3,878 sqft
125 S INTERLACHEN AVENUE # 1, WINTER PARK, FL 32789
317 Days on Market
House for Sale
$3,650,000
5 bd · 5 ba · 3,719 sqft
207 E KINGS WAY, WINTER PARK, FL 32789
Newly Listed
House for Sale
$3,500,000
5 bd · 7 ba · 4,168 sqft
1836 WHITEHALL DRIVE, WINTER PARK, FL 32789
Newly Listed
House for Sale
$3,500,000
5 bd · 6 ba · 4,831 sqft
1901 LOCH BERRY ROAD, WINTER PARK, FL 32792
11 Days on Market
Townhome for Sale
$3,500,000
3 bd · 5 ba · 3,180 sqft
649 N PARK AVENUE, WINTER PARK, FL 32789
46 Days on Market
House for Sale
$3,500,000
4 bd · 4 ba · 4,036 sqft
2240 VENETIAN WAY, WINTER PARK, FL 32789
15 Days on Market
House for Sale
$3,300,000
5 bd · 6 ba · 3,421 sqft
1627 MIZELL AVENUE, WINTER PARK, FL 32789
136 Days on Market
House for Sale
$3,275,000
4 bd · 6 ba · 4,683 sqft
1581 FOREST AVENUE, WINTER PARK, FL 32789
274 Days on Market
House for Sale
$3,235,000
5 bd · 6 ba · 3,863 sqft
1821 ENGLEWOOD ROAD, WINTER PARK, FL 32789
Newly Listed
House for Sale
$3,199,000
4 bd · 5 ba · 3,737 sqft
361 E KINGS WAY, WINTER PARK, FL 32789
Newly Listed
Townhome for Sale
$3,150,000
3 bd · 5 ba · 3,244 sqft
125 S INTERLACHEN AVENUE # 2, WINTER PARK, FL 32789
43 Days on Market
Townhome for Sale
$2,800,000
3 bd · 4 ba · 3,286 sqft
660 W MORSE BOULEVARD, WINTER PARK, FL 32789
17 Days on Market
Townhome for Sale
$2,695,000
3 bd · 4 ba · 3,048 sqft
413 W MORSE BOULEVARD, WINTER PARK, FL 32789
95 Days on Market
House for Sale
$2,650,000
4 bd · 4 ba · 3,553 sqft
541 W CANTON AVENUE, WINTER PARK, FL 32789
Newly Listed
House for Sale
$2,569,999
5 bd · 5 ba · 3,670 sqft
1754 TAYLOR AVENUE, WINTER PARK, FL 32789
14 Days on Market
House for Sale
$2,549,000
5 bd · 5 ba · 3,479 sqft
1823 SUNSET DRIVE, WINTER PARK, FL 32789
78 Days on Market
House for Sale
$2,500,000
5 bd · 6 ba · 4,572 sqft
450 LAKEWOOD DRIVE, WINTER PARK, FL 32789
44 Days on Market
House for Sale
$2,460,000
4 bd · 4 ba · 3,294 sqft
2228 HOWARD DRIVE, WINTER PARK, FL 32789
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Live MLS inventory in Winter Park, updated continuously. Florida Lux Real Estate currently tracks 301 active listings here. MLS inventory updated October 13, 2026.
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