Winter Park 2+ Bedroom Homes for Sale

18 Days on Market

House for Sale

$1,995,000

4 bd · 4 ba · 3,440 sqft

922 N PENNSYLVANIA AVENUE, WINTER PARK, FL 32789

58 Days on Market

House for Sale

$1,899,000

5 bd · 5 ba · 3,620 sqft

910 ENCLAVE PLACE, WINTER PARK, FL 32792

113 Days on Market

House for Sale

$1,895,000

5 bd · 5 ba · 3,617 sqft

914 ENCLAVE PLACE, WINTER PARK, FL 32792

79 Days on Market

House for Sale

$1,895,000

3 bd · 4 ba · 2,767 sqft

622 PENN PLACE, WINTER PARK, FL 32789

25 Days on Market

Condo for Sale

$1,849,900

3 bd · 4 ba · 3,112 sqft

101 S NEW YORK AVENUE # 311, WINTER PARK, FL 32789

89 Days on Market

Condo for Sale

$1,825,000

2 bd · 2 ba · 2,304 sqft

311 E MORSE BOULEVARD # 1-3, WINTER PARK, FL 32789

14 Days on Market

House for Sale

$1,800,000

5 bd · 5 ba · 4,029 sqft

281 BREWER AVENUE, WINTER PARK, FL 32789

58 Days on Market

House for Sale

$1,800,000

5 bd · 4 ba · 3,382 sqft

2032 KIMBRACE PLACE, WINTER PARK, FL 32792

61 Days on Market

House for Sale

$1,800,000

4 bd · 4 ba · 3,065 sqft

723 SYMONDS AVENUE, WINTER PARK, FL 32789

57 Days on Market

House for Sale

$1,795,000

3 bd · 4 ba · 2,399 sqft

621 HUNTINGTON AVENUE, 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

Newly Listed

House for Sale

$1,775,000

4 bd · 5 ba · 3,630 sqft

890 N PHELPS AVENUE, WINTER PARK, FL 32789

197 Days on Market

House for Sale

$1,750,000

4 bd · 3 ba · 2,350 sqft

1840 ANZLE AVENUE, WINTER PARK, FL 32789

Newly Listed

House for Sale

$1,749,000

4 bd · 4 ba · 2,715 sqft

2525 LAFAYETTE AVENUE, WINTER PARK, FL 32789

35 Days on Market

House for Sale

$1,725,000

6 bd · 6 ba · 4,173 sqft

2914 REEF KNOT PLACE, WINTER PARK, FL 32792

Newly Listed

House for Sale

$1,725,000

4 bd · 4 ba · 3,727 sqft

1840 BRYAN AVENUE, WINTER PARK, FL 32789

51 Days on Market

House for Sale

$1,695,000

4 bd · 4 ba · 3,174 sqft

1420 MAGNOLIA AVENUE, WINTER PARK, FL 32789

141 Days on Market

House for Sale

$1,695,000

4 bd · 4 ba · 2,807 sqft

1903 N PARK AVENUE, WINTER PARK, FL 32789

Newly Listed

House for Sale

$1,690,000

4 bd · 3 ba · 2,786 sqft

708 BALMORAL ROAD, WINTER PARK, FL 32789

135 Days on Market

House for Sale

$1,649,000

5 bd · 4 ba · 3,304 sqft

2501 WINTER PARK ROAD, WINTER PARK, FL 32789

73 Days on Market

House for Sale

$1,625,000

4 bd · 2 ba · 2,640 sqft

446 MELROSE AVENUE, WINTER PARK, FL 32789

33 Days on Market

House for Sale

$1,625,000

4 bd · 4 ba · 3,723 sqft

341 E READING WAY, WINTER PARK, FL 32789

Newly Listed

House for Sale

$1,600,000

4 bd · 4 ba · 2,568 sqft

250 KILLARNEY, WINTER PARK, FL 32789

61 Days on Market

House for Sale

$1,599,000

3 bd · 5 ba · 2,756 sqft

641 NORTHWOOD CIRCLE, 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

Send a message

We reply the same day.

Send Inquiry

By submitting you agree to be contacted about your inquiry. No spam, ever.

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 26, 2026.