155 Days on Market
House for Sale
$500,000
4 bd · 2 ba · 1,979 sqft
Bedrooms
Bathrooms
Winter Springs Homes for Sale under $500K
91 listings
92 Days on Market
House for Sale
$499,999
3 bd · 3 ba · 2,378 sqft
1200 ROYAL OAK DRIVE, WINTER SPRINGS, FL 32708
Newly Listed
House for Sale
$498,000
4 bd · 4 ba · 2,510 sqft
225 GENTLE BREEZE LANE, WINTER SPRINGS, FL 32708
63 Days on Market
House for Sale
$490,000
3 bd · 2 ba · 1,665 sqft
1055 CHESTERFIELD CIRCLE, WINTER SPRINGS, FL 32708
9 Days on Market
Townhome for Sale
$489,900
2 bd · 3 ba · 1,926 sqft
1541 CORKERY COURT # 1541, WINTER SPRINGS, FL 32708
77 Days on Market
House for Sale
$488,000
4 bd · 3 ba · 2,152 sqft
1304 ORTEGA STREET, WINTER SPRINGS, FL 32708
155 Days on Market
House for Sale
$484,900
4 bd · 3 ba · 1,996 sqft
632 BLENHEIM LOOP, WINTER SPRINGS, FL 32708
126 Days on Market
House for Sale
$479,000
3 bd · 2 ba · 1,978 sqft
107 GOLDEN CREST COURT, WINTER SPRINGS, FL 32708
28 Days on Market
House for Sale
$479,000
3 bd · 2 ba · 1,814 sqft
114 STONE GABLE CIRCLE, WINTER SPRINGS, FL 32708
58 Days on Market
Townhome for Sale
$475,000
4 bd · 4 ba · 2,359 sqft
1320 SPOTTED SANDPIPER LOOP, WINTER SPRINGS, FL 32708
83 Days on Market
House for Sale
$475,000
3 bd · 2 ba · 1,857 sqft
629 RYAN COURT, WINTER SPRINGS, FL 32708
14 Days on Market
House for Sale
$464,000
3 bd · 2 ba · 1,919 sqft
619 CORAL WAY, WINTER SPRINGS, FL 32708
113 Days on Market
Townhome for Sale
$459,900
4 bd · 4 ba · 2,344 sqft
1128 SPOTTED SANDPIPER LOOP, WINTER SPRINGS, FL 32708
23 Days on Market
House for Sale
$450,000
3 bd · 2 ba · 1,612 sqft
1454 KING COURT, WINTER SPRINGS, FL 32708
333 Days on Market
House for Sale
$449,000
3 bd · 3 ba · 2,147 sqft
122 STONE GABLE CIR, WINTER SPRINGS, FL 32708
Newly Listed
House for Sale
$435,000
3 bd · 2 ba · 2,116 sqft
1298 MADELENA AVENUE, WINTER SPRINGS, FL 32708
38 Days on Market
House for Sale
$429,900
2 bd · 2 ba · 1,812 sqft
717 ADIDAS ROAD, WINTER SPRINGS, FL 32708
15 Days on Market
House for Sale
$425,900
3 bd · 3 ba · 2,063 sqft
1375 AUGUSTA NATIONAL BOULEVARD, WINTER SPRINGS, FL 32708
Newly Listed
Townhome for Sale
$425,000
3 bd · 4 ba · 2,068 sqft
1380 MILL STREAM LANE, WINTER SPRINGS, FL 32708
14 Days on Market
House for Sale
$425,000
3 bd · 2 ba · 1,831 sqft
963 SEQUOIA DRIVE, WINTER SPRINGS, FL 32708
39 Days on Market
Townhome for Sale
$424,990
4 bd · 3 ba · 1,678 sqft
221 SPINDLE PALM COVE, WINTER SPRINGS, FL 32708
156 Days on Market
House for Sale
$423,997
3 bd · 2 ba · 1,554 sqft
872 FALKIRK DRIVE, WINTER SPRINGS, FL 32708
18 Days on Market
House for Sale
$420,000
4 bd · 3 ba · 2,150 sqft
758 N GRETNA COURT, WINTER SPRINGS, FL 32708
76 Days on Market
Townhome for Sale
$420,000
3 bd · 3 ba · 1,476 sqft
1406 BLUMBERG BOULEVARD, WINTER SPRINGS, FL 32708
Talk to a local agent
Looking at Winter Springs Homes for Sale under $500K?
Tell us what you're after — we'll send matching homes, off-market options and recent sales, and set up private showings.
Live MLS inventory in Winter Springs, updated continuously. Florida Lux Real Estate currently tracks 91 active listings here. MLS inventory updated October 17, 2026.