Winter Park 5+ Bedroom Homes for Sale

170 Days on Market

House for Sale

$8,950,000

7 bd · 11 ba · 11,255 sqft

1120 PRESERVE POINT DRIVE, WINTER PARK, FL 32789

178 Days on Market

House for Sale

$7,250,000

5 bd · 6 ba · 5,905 sqft

40 PALMER AVENUE, WINTER PARK, FL 32789

152 Days on Market

House for Sale

$6,900,000

6 bd · 7 ba · 6,396 sqft

1260 ALABAMA DRIVE, WINTER PARK, FL 32789

21 Days on Market

House for Sale

$6,000,000

5 bd · 8 ba · 7,397 sqft

1571 WOODLAND AVENUE, WINTER PARK, FL 32789

41 Days on Market

House for Sale

$5,600,000

5 bd · 6 ba · 5,152 sqft

2228 AZALEA PLACE, WINTER PARK, FL 32789

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

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

15 Days on Market

House for Sale

$3,300,000

5 bd · 6 ba · 3,421 sqft

1627 MIZELL 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

$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

104 Days on Market

House for Sale

$2,399,000

5 bd · 5 ba · 3,479 sqft

2838 WRIGHT AVENUE, WINTER PARK, FL 32789

Newly Listed

House for Sale

$2,299,000

5 bd · 5 ba · 2,868 sqft

1840 LAUREL ROAD, WINTER PARK, FL 32789

52 Days on Market

House for Sale

$2,235,000

5 bd · 5 ba · 4,150 sqft

926 ENCLAVE PLACE, WINTER PARK, FL 32792

44 Days on Market

House for Sale

$2,195,000

5 bd · 5 ba · 3,831 sqft

942 ENCLAVE PLACE, WINTER PARK, FL 32792

252 Days on Market

House for Sale

$2,195,000

5 bd · 4 ba · 3,691 sqft

1885 TEMPLE DRIVE, WINTER PARK, FL 32789

44 Days on Market

House for Sale

$2,175,000

5 bd · 5 ba · 3,989 sqft

946 ENCLAVE PLACE, WINTER PARK, FL 32792

52 Days on Market

House for Sale

$2,150,000

5 bd · 5 ba · 2,889 sqft

240 N PHELPS AVENUE, WINTER PARK, FL 32789

44 Days on Market

House for Sale

$2,125,000

5 bd · 5 ba · 3,797 sqft

950 ENCLAVE PLACE, WINTER PARK, FL 32792

52 Days on Market

House for Sale

$2,099,000

5 bd · 5 ba · 3,865 sqft

938 ENCLAVE PLACE, WINTER PARK, FL 32792

Talk to a local agent

Looking at Winter Park 5+ Bedroom Homes?

Tell us what you're after — we'll send matching homes, off-market options and recent sales, and set up private showings.

Matthew Gromadzki

Real Estate Broker

(786) 370-8570

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Live MLS inventory in Winter Park, updated continuously. Showing homes with 5 or more bedrooms. Florida Lux Real Estate currently tracks 41 active listings here. MLS inventory updated October 12, 2026.