57 Days on Market
House for Sale
$399,990
3 bd · 2 ba · 1,366 sqft
Bedrooms
Bathrooms
Winter Park Homes for Sale under $400K
99 listings
Newly Listed
Townhome for Sale
$399,900
3 bd · 3 ba · 1,907 sqft
2017 CANNY COVE, WINTER PARK, FL 32792
339 Days on Market
House for Sale
$399,900
4 bd · 2 ba · 1,627 sqft
1849 VIBURNUM LANE, WINTER PARK, FL 32792
36 Days on Market
House for Sale
$399,800
4 bd · 2 ba · 1,808 sqft
1610 GLADIOLAS DRIVE, WINTER PARK, FL 32792
19 Days on Market
Townhome for Sale
$399,000
3 bd · 3 ba · 1,907 sqft
2033 CANNY COVE, WINTER PARK, FL 32792
11 Days on Market
House for Sale
$399,000
3 bd · 2 ba · 1,122 sqft
1092 EASTBROOK BOULEVARD, WINTER PARK, FL 32792
Newly Listed
House for Sale
$390,000
4 bd · 2 ba · 1,607 sqft
2512 EASTBROOK BOULEVARD, WINTER PARK, FL 32792
40 Days on Market
House for Sale
$389,000
3 bd · 2 ba · 1,285 sqft
1605 PURITAN AVENUE, WINTER PARK, FL 32792
12 Days on Market
House for Sale
$385,000
4 bd · 2 ba · 1,240 sqft
885 CARNATION DRIVE, WINTER PARK, FL 32792
59 Days on Market
Condo for Sale
$380,000
1 bd · 1 ba · 987 sqft
700 MELROSE AVENUE # J24, WINTER PARK, FL 32789
27 Days on Market
House for Sale
$379,900
4 bd · 2 ba · 1,444 sqft
4965 ORANGE AVENUE, WINTER PARK, FL 32792
Newly Listed
Townhome for Sale
$375,000
3 bd · 3 ba · 1,872 sqft
7522 ALOMA PINES COURT, WINTER PARK, FL 32792
47 Days on Market
House for Sale
$369,900
2 bd · 1 ba · 988 sqft
440 CAMBRIDGE BOULEVARD, WINTER PARK, FL 32789
94 Days on Market
House for Sale
$360,000
3 bd · 3 ba · 1,397 sqft
3374 HAMLET LOOP, WINTER PARK, FL 32792
Newly Listed
House for Sale
$354,999
3 bd · 2 ba · 1,344 sqft
310 GRANADA DRIVE, WINTER PARK, FL 32789
Newly Listed
House for Sale
$350,000
3 bd · 2 ba · 1,268 sqft
7261 ABBEY LANE, WINTER PARK, FL 32792
28 Days on Market
Townhome for Sale
$350,000
3 bd · 3 ba · 1,682 sqft
2521 GALLIANO CIRCLE, WINTER PARK, FL 32792
Newly Listed
House for Sale
$349,900
3 bd · 2 ba · 1,397 sqft
3328 HAMLET LOOP, WINTER PARK, FL 32792
Newly Listed
House for Sale
$349,000
2 bd · 1 ba · 749 sqft
811 OVERSPIN DRIVE, WINTER PARK, FL 32789
Newly Listed
House for Sale
$339,000
3 bd · 2 ba · 1,149 sqft
3562 BOUGAINVILLEA DRIVE, WINTER PARK, FL 32792
Newly Listed
Condo for Sale
$335,000
3 bd · 3 ba · 1,790 sqft
2526 PASSAMONTE DRIVE # 10F, WINTER PARK, FL 32792
65 Days on Market
House for Sale
$328,000
2 bd · 1 ba · 797 sqft
2006 CORNELL AVENUE, WINTER PARK, FL 32789
16 Days on Market
House for Sale
$325,000
3 bd · 2 ba · 1,518 sqft
7393 GRAND AVENUE, WINTER PARK, FL 32792
30 Days on Market
Home for Sale
$320,000
2 bd · 2 ba · 1,086 sqft
5781 SHALE COURT, WINTER PARK, FL 32792
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Live MLS inventory in Winter Park, updated continuously. Florida Lux Real Estate currently tracks 99 active listings here. MLS inventory updated October 22, 2026.
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