Winter Park Homes for Sale under $500K

Live MLS inventory in Winter Park, updated continuously.

$500,000

3 bd · 2 ba · 1,433 sqft

2974 CHANTILLY AVENUE, WINTER PARK, FL 32789

$500,000

4 bd · 3 ba · 2,031 sqft

2054 EASTBROOK BOULEVARD, WINTER PARK, FL 32792

$500,000

3 bd · 2 ba · 1,413 sqft

512 N LAKEMONT AVENUE, WINTER PARK, FL 32792

$499,900New

3 bd · 2 ba · 1,979 sqft

351 STARLING ROAD, WINTER PARK, FL 32789

$499,000

3 bd · 3 ba · 1,818 sqft

1807 HAMMERLIN AVENUE # G, WINTER PARK, FL 32789

$499,000

2 bd · 1 ba · 857 sqft

981 ARAGON AVENUE, WINTER PARK, FL 32789

$495,900

3 bd · 3 ba · 1,786 sqft

525 OLOLU DRIVE, WINTER PARK, FL 32789

$495,000New

3 bd · 2 ba · 1,380 sqft

5316 HALYARD COURT, WINTER PARK, FL 32792

$494,900

3 bd · 2 ba · 1,565 sqft

2715 PRINCE JOHN ROAD, WINTER PARK, FL 32792

$490,000

4 bd · 2 ba · 2,250 sqft

2008 HOUNDSLAKE DRIVE, WINTER PARK, FL 32792

$475,000

2 bd · 3 ba · 1,428 sqft

630 KILLARNEY BAY COURT # 3, WINTER PARK, FL 32789

$474,000

4 bd · 2 ba · 1,624 sqft

1320 GLADIOLAS DR, WINTER PARK, FL 32792

$469,000New

3 bd · 2 ba · 1,737 sqft

2703 TIERRA CIRCLE, WINTER PARK, FL 32792

$465,000

3 bd · 2 ba · 1,622 sqft

3641 HAWTHORNE LANE, WINTER PARK, FL 32792

$460,000

3 bd · 2 ba · 1,606 sqft

950 HANOVER AVENUE, WINTER PARK, FL 32789

$460,000

3 bd · 2 ba · 1,263 sqft

5331 OAK COURT, WINTER PARK, FL 32792

$460,000

3 bd · 2 ba · 1,703 sqft

1052 MANCHESTER CIRCLE, WINTER PARK, FL 32792

$460,000New

3 bd · 2 ba · 1,521 sqft

2826 AMBERGATE ROAD, WINTER PARK, FL 32792

$459,900

3 bd · 2 ba · 1,248 sqft

259 ORANGE TERRACE DRIVE, WINTER PARK, FL 32789

$450,000

4 bd · 2 ba · 1,651 sqft

316 BECKETT COURT, WINTER PARK, FL 32792

$449,900

3 bd · 2 ba · 1,746 sqft

5340 N LAKE BURKETT LANE, WINTER PARK, FL 32792

$449,900

4 bd · 2 ba · 1,376 sqft

501 HERITAGE BOULEVARD, WINTER PARK, FL 32792

$449,000New

3 bd · 2 ba · 1,154 sqft

2007 CORNELL AVENUE, WINTER PARK, FL 32789

$439,900

3 bd · 1 ba · 1,508 sqft

2041 JEWELL AVENUE, WINTER PARK, FL 32789