57 Days on Market
House for Sale
$500,000
3 bd · 2 ba · 1,433 sqft
Bedrooms
Bathrooms
Winter Park Homes for Sale under $500K
137 listings
68 Days on Market
House for Sale
$500,000
4 bd · 3 ba · 2,031 sqft
2054 EASTBROOK BOULEVARD, WINTER PARK, FL 32792
133 Days on Market
House for Sale
$500,000
3 bd · 2 ba · 1,413 sqft
512 N LAKEMONT AVENUE, WINTER PARK, FL 32792
Newly Listed
House for Sale
$499,900
3 bd · 2 ba · 1,979 sqft
351 STARLING ROAD, WINTER PARK, FL 32789
35 Days on Market
House for Sale
$499,000
2 bd · 1 ba · 857 sqft
981 ARAGON AVENUE, WINTER PARK, FL 32789
144 Days on Market
Condo for Sale
$499,000
3 bd · 3 ba · 1,818 sqft
1807 HAMMERLIN AVENUE # G, WINTER PARK, FL 32789
85 Days on Market
House for Sale
$495,900
3 bd · 3 ba · 1,786 sqft
525 OLOLU DRIVE, WINTER PARK, FL 32789
Newly Listed
House for Sale
$495,000
3 bd · 2 ba · 1,380 sqft
5316 HALYARD COURT, WINTER PARK, FL 32792
43 Days on Market
House for Sale
$494,900
3 bd · 2 ba · 1,565 sqft
2715 PRINCE JOHN ROAD, WINTER PARK, FL 32792
35 Days on Market
House for Sale
$490,000
4 bd · 2 ba · 2,250 sqft
2008 HOUNDSLAKE DRIVE, WINTER PARK, FL 32792
128 Days on Market
Condo for Sale
$475,000
2 bd · 3 ba · 1,428 sqft
630 KILLARNEY BAY COURT # 3, WINTER PARK, FL 32789
60 Days on Market
House for Sale
$474,000
4 bd · 2 ba · 1,624 sqft
1320 GLADIOLAS DR, WINTER PARK, FL 32792
Newly Listed
House for Sale
$469,000
3 bd · 2 ba · 1,737 sqft
2703 TIERRA CIRCLE, WINTER PARK, FL 32792
37 Days on Market
House for Sale
$465,000
3 bd · 2 ba · 1,622 sqft
3641 HAWTHORNE LANE, WINTER PARK, FL 32792
139 Days on Market
House for Sale
$460,000
3 bd · 2 ba · 1,263 sqft
5331 OAK COURT, WINTER PARK, FL 32792
Newly Listed
House for Sale
$460,000
3 bd · 2 ba · 1,521 sqft
2826 AMBERGATE ROAD, WINTER PARK, FL 32792
134 Days on Market
House for Sale
$460,000
3 bd · 2 ba · 1,703 sqft
1052 MANCHESTER CIRCLE, WINTER PARK, FL 32792
118 Days on Market
House for Sale
$460,000
3 bd · 2 ba · 1,606 sqft
950 HANOVER AVENUE, WINTER PARK, FL 32789
27 Days on Market
House for Sale
$459,900
3 bd · 2 ba · 1,248 sqft
259 ORANGE TERRACE DRIVE, WINTER PARK, FL 32789
54 Days on Market
House for Sale
$450,000
4 bd · 2 ba · 1,651 sqft
316 BECKETT COURT, WINTER PARK, FL 32792
59 Days on Market
House for Sale
$449,900
3 bd · 2 ba · 1,746 sqft
5340 N LAKE BURKETT LANE, 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
Newly Listed
House for Sale
$449,000
3 bd · 2 ba · 1,154 sqft
2007 CORNELL AVENUE, WINTER PARK, FL 32789
18 Days on Market
House for Sale
$439,900
3 bd · 1 ba · 1,508 sqft
2041 JEWELL AVENUE, WINTER PARK, FL 32789
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Live MLS inventory in Winter Park, updated continuously. Florida Lux Real Estate currently tracks 137 active listings here. MLS inventory updated October 25, 2026.
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