Winter Park Luxury 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

10 Days on Market

House for Sale

$5,500,000

4 bd · 5 ba · 4,775 sqft

313 SYLVAN DRIVE, WINTER PARK, FL 32789

20 Days on Market

House for Sale

$4,950,000

4 bd · 7 ba · 5,550 sqft

231 CHELTON CIRCLE, 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

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

46 Days on Market

House for Sale

$3,500,000

4 bd · 4 ba · 4,036 sqft

2240 VENETIAN WAY, WINTER PARK, FL 32789

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

Newly Listed

House for Sale

$3,500,000

5 bd · 6 ba · 4,831 sqft

1901 LOCH BERRY ROAD, WINTER PARK, FL 32792

Newly Listed

House for Sale

$3,500,000

5 bd · 7 ba · 4,168 sqft

1836 WHITEHALL DRIVE, 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

Talk to a local agent

Looking at Winter Park Luxury 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. Florida Lux Real Estate currently tracks 105 active listings here. MLS inventory updated October 13, 2026.