Winter Park 2+ Bedroom Homes for Sale

66 Days on Market

House for Sale

$1,599,000

5 bd · 4 ba · 3,028 sqft

1864 GRINNELL TERRACE, WINTER PARK, FL 32789

86 Days on Market

House for Sale

$1,599,000

4 bd · 4 ba · 2,916 sqft

2430 CHANTILLY AVENUE, WINTER PARK, FL 32789

65 Days on Market

House for Sale

$1,595,000

3 bd · 4 ba · 2,467 sqft

1841 LAKE SPIER DRIVE, WINTER PARK, FL 32789

164 Days on Market

House for Sale

$1,595,000

3 bd · 2 ba · 2,012 sqft

1113 VIA DEL MAR, WINTER PARK, FL 32789

Newly Listed

House for Sale

$1,595,000

3 bd · 3 ba · 1,944 sqft

462 W LYMAN AVENUE, WINTER PARK, FL 32789

Newly Listed

House for Sale

$1,500,000

5 bd · 5 ba · 3,109 sqft

777 HALIFAX AVENUE, WINTER PARK, FL 32792

113 Days on Market

Townhome for Sale

$1,495,000

4 bd · 4 ba · 2,738 sqft

901 ENCLAVE PLACE, WINTER PARK, FL 32792

113 Days on Market

Townhome for Sale

$1,495,000

4 bd · 4 ba · 2,756 sqft

905 ENCLAVE PLACE, WINTER PARK, FL 32792

62 Days on Market

House for Sale

$1,465,000

4 bd · 4 ba · 2,756 sqft

1581 MAGNOLIA AVE, WINTER PARK, FL 32789

42 Days on Market

House for Sale

$1,450,000

3 bd · 2 ba · 1,747 sqft

120 BROADVIEW AVENUE, WINTER PARK, FL 32789

57 Days on Market

House for Sale

$1,450,000

4 bd · 4 ba · 3,578 sqft

1421 CHAPMAN CIRCLE, WINTER PARK, FL 32789

157 Days on Market

House for Sale

$1,449,999

5 bd · 4 ba · 3,164 sqft

1523 MILLER AVENUE, WINTER PARK, FL 32789

58 Days on Market

House for Sale

$1,429,000

5 bd · 4 ba · 2,351 sqft

1473 BERKSHIRE AVENUE, WINTER PARK, FL 32789

Newly Listed

House for Sale

$1,419,900

4 bd · 4 ba · 2,984 sqft

1546 MILLER AVENUE, WINTER PARK, FL 32789

23 Days on Market

Townhome for Sale

$1,399,000

3 bd · 3 ba · 2,585 sqft

512 W SWOOPE AVENUE, WINTER PARK, FL 32789

291 Days on Market

House for Sale

$1,389,500

4 bd · 5 ba · 2,812 sqft

607 ELLEN DRIVE, WINTER PARK, FL 32789

155 Days on Market

House for Sale

$1,380,000

4 bd · 4 ba · 2,170 sqft

1751 GOODRICH AVENUE, WINTER PARK, FL 32789

Newly Listed

House for Sale

$1,350,000

3 bd · 2 ba · 1,750 sqft

1881 LAKE SPIER DRIVE, 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

91 Days on Market

House for Sale

$1,295,000

4 bd · 4 ba · 2,843 sqft

802 HAMILTON PLACE COURT, WINTER PARK, FL 32789

11 Days on Market

House for Sale

$1,275,000

3 bd · 3 ba · 1,329 sqft

240 KILLARNEY DRIVE, WINTER PARK, FL 32789

51 Days on Market

House for Sale

$1,262,500

4 bd · 4 ba · 3,024 sqft

2015 SUMMERFIELD ROAD, WINTER PARK, FL 32792

126 Days on Market

House for Sale

$1,250,000

4 bd · 4 ba · 2,525 sqft

1870 STAUNTON AVENUE, WINTER PARK, FL 32789

11 Days on Market

House for Sale

$1,250,000

4 bd · 1 ba · 1,260 sqft

230 KILLARNEY DRIVE, WINTER PARK, FL 32789

Talk to a local agent

Looking at Winter Park 2+ 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 2 or more bedrooms. Florida Lux Real Estate currently tracks 281 active listings here. MLS inventory updated October 29, 2026.