Homes under $500K in Winter Springs, FL

90 for sale · 194 homes listed · Updated September 27, 2026 · Page 2 of 4

• 212 south cortez avenue, Winter Springs 32708 $375,000 · 4 bd · 3 ba · 1,344 sqft
• 1298 madelena avenue, Winter Springs 32708 $434,900 · 3 bd · 2 ba · 2,116 sqft
• 311 san miguel street, Winter Springs 32708 $178,900 · 2 bd · 2 ba · 945 sqft
• 923 torrey pine drive, Winter Springs 32708 $360,000 · 2 bd · 2 ba · 1,193 sqft
• 70 moree loop 61, Winter Springs 32708 $179,900 · 2 bd · 2 ba · 1,080 sqft
• 998 white springs lane, Winter Springs 32708 $429,900 · 3 bd · 2 ba · 1,587 sqft
• 662 nighthawk circle, Winter Springs 32708 $374,400 · 3 bd · 3 ba · 1,583 sqft
• 1307 park villa place, Winter Springs 32708 $239,900 · 2 bd · 2 ba · 1,156 sqft
• 611 casa park a court, Winter Springs 32708 $234,900 · 2 bd · 3 ba · 1,156 sqft
• 272 san gabriel street, Winter Springs 32708 $275,000 · 3 bd · 2 ba · 1,105 sqft
• 311 san miguel street 311, Winter Springs 32708 $178,900 · 2 bd · 2 ba · 945 sqft
• 736 summerland drive, Winter Springs 32708 $295,900 · 3 bd · 2 ba · 1,298 sqft
• 600 northern way 1108, Winter Springs 32708 $267,500 · 3 bd · 3 ba · 1,411 sqft
• 806 big buck circle, Winter Springs 32708 $435,000 · 3 bd · 2 ba · 1,887 sqft
• 412 horizon drive, Winter Springs 32708 $284,000 · 3 bd · 2 ba · 1,101 sqft
• 1162 east winged foot circle, Winter Springs 32708 $425,000 · 3 bd · 2 ba · 1,574 sqft
• 1142 oday drive, Winter Springs 32708 $490,000 · 4 bd · 3 ba · 2,300 sqft
• 203 cottonwood drive, Winter Springs 32708 $349,000 · 3 bd · 2 ba · 1,168 sqft
• 1482 creekside circle, Winter Springs 32708 $344,900 · 3 bd · 3 ba · 1,605 sqft
• 1406 blumberg boulevard, Winter Springs 32708 $399,000 · 3 bd · 3 ba · 1,476 sqft
• 412 blue bayou lane, Winter Springs 32708 $369,500 · 3 bd · 4 ba · 1,854 sqft
• 1714 fox glen court, Winter Springs 32708 $439,000 · 3 bd · 2 ba · 1,484 sqft
• 744 barrington circle, Winter Springs 32708 $425,000 · 3 bd · 2 ba · 1,658 sqft
• 625 pearl road, Winter Springs 32708 $439,900 · 3 bd · 3 ba · 1,730 sqft
• 1610 fox glen court, Winter Springs 32708 $497,000 · 4 bd · 3 ba · 1,992 sqft
• 909 devon creek road, Winter Springs 32708 $499,900 · 4 bd · 3 ba · 2,256 sqft
• 113 kristi ann court, Winter Springs 32708 $210,000 · 2 bd · 2 ba · 898 sqft
• 417 sheoah boulevard 17, Winter Springs 32708 $170,000 · 2 bd · 2 ba · 936 sqft
• 288 ringwood drive, Winter Springs 32708 $475,000 · 3 bd · 2 ba · 1,700 sqft
• 654 cypress lane, Winter Springs 32708 $325,000 · 3 bd · 2 ba · 1,201 sqft
• 1125 shadowbrook trail, Winter Springs 32708 $230,000 · 4 bd · 3 ba · 2,361 sqft
• 1010 west pebble beach circle, Winter Springs 32708 $499,999 · 3 bd · 3 ba · 1,732 sqft
• 512 pinebranch circle, Winter Springs 32708 $330,000 · 2 bd · 3 ba · 1,558 sqft
• 205 inkwood court, Winter Springs 32708 $429,000 · 3 bd · 2 ba · 1,748 sqft
• 414 horizon drive, Winter Springs 32708 $309,000 · 3 bd · 2 ba · 1,101 sqft
• 1394 san luis court, Winter Springs 32708 $269,900 · 2 bd · 2 ba · 1,153 sqft
• 627 murphy road, Winter Springs 32708 $309,000 · 3 bd · 2 ba · 1,260 sqft
• 813 leopard trail, Winter Springs 32708 $399,900 · 3 bd · 2 ba · 1,550 sqft
• 130 rhoden lane, Winter Springs 32708 $220,000 · 2 bd · 2 ba · 896 sqft
• 1044 forest circle, Winter Springs 32708 $450,000 · 3 bd · 2 ba · 1,652 sqft
• 712 linden drive, Winter Springs 32708 Pending $300,000 · 3 bd · 2 ba · 1,366 sqft
• 448 macgregor road, Winter Springs 32708 Pending $350,000 · 2 bd · 2 ba · 1,477 sqft
• 572 pinebranch circle, Winter Springs 32708 Pending $330,000 · 3 bd · 3 ba · 1,564 sqft
• 1384 mill stream lane, Winter Springs 32708 Pending $360,000 · 3 bd · 4 ba · 1,932 sqft
• 510 green spring circle, Winter Springs 32708 Pending $211,000 · 2 bd · 3 ba · 1,180 sqft
• 600 northern way 1804, Winter Springs 32708 Pending $290,000 · 4 bd · 3 ba · 1,726 sqft
• 665 murphy road, Winter Springs 32708 Pending $380,000 · 3 bd · 2 ba · 1,460 sqft
• 1407 tarflower drive, Winter Springs 32708 Pending $386,990 · 3 bd · 3 ba · 1,476 sqft
• 1403 tarflower drive, Winter Springs 32708 Pending $401,990 · 3 bd · 3 ba · 1,678 sqft
• 930 oak forest drive, Winter Springs 32708 Pending $450,000 · 4 bd · 2 ba · 1,764 sqft