Winter Park Homes with a Pool for Sale

10 Days on Market

House for Sale

$5,500,000

4 bd · 5 ba · 4,775 sqft

313 SYLVAN 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

136 Days on Market

House for Sale

$3,275,000

4 bd · 6 ba · 4,683 sqft

1581 FOREST 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

Newly Listed

House for Sale

$2,299,000

5 bd · 5 ba · 2,868 sqft

1840 LAUREL ROAD, WINTER PARK, FL 32789

Newly Listed

House for Sale

$2,275,000

4 bd · 5 ba · 2,835 sqft

1271 PALMER AVENUE, 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

100 Days on Market

House for Sale

$1,995,000

4 bd · 4 ba · 3,450 sqft

1398 GROVE TERRACE, WINTER PARK, FL 32789

125 Days on Market

House for Sale

$1,780,000

4 bd · 4 ba · 3,249 sqft

1750 CAROLLEE LANE, WINTER PARK, FL 32789

66 Days on Market

House for Sale

$1,599,000

5 bd · 4 ba · 3,028 sqft

1864 GRINNELL TERRACE, WINTER PARK, FL 32789

107 Days on Market

House for Sale

$1,349,000

4 bd · 4 ba · 2,459 sqft

102 BELL PLACE, WINTER PARK, FL 32792

76 Days on Market

Condo for Sale

$989,500

1 bd · 2 ba · 1,109 sqft

269 E CANTON AVENUE # 269, WINTER PARK, FL 32789

31 Days on Market

House for Sale

$775,000

5 bd · 3.5 ba · 2,840 sqft

1164 Dodd Road, Winter Park, FL 32792

Newly Listed

House for Sale

$765,000

4 bd · 3 ba · 2,673 sqft

110 LONGHORN ROAD, WINTER PARK, FL 32792

143 Days on Market

House for Sale

$449,900

4 bd · 2 ba · 1,376 sqft

501 HERITAGE BOULEVARD, WINTER PARK, FL 32792

Talk to a local agent

Looking at Winter Park Homes with a Pool?

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 16 active listings here. MLS inventory updated October 12, 2026.