Homes under $500K in Winter Springs, FL

90 for sale · 194 homes listed · Updated September 27, 2026 · Page 3 of 4

• 1375 augusta national boulevard, Winter Springs 32708 Pending $409,900 · 3 bd · 3 ba · 2,063 sqft
• 162 constitution way, Winter Springs 32708 Pending $289,900 · 3 bd · 3 ba · 1,468 sqft
• 233 spindle palm cove, Winter Springs 32708 Pending $386,990 · 3 bd · 3 ba · 1,476 sqft
• 405 north hawthorn circle, Winter Springs 32708 Pending $318,000 · 3 bd · 2 ba · 1,656 sqft
• 655 nighthawk circle, Winter Springs 32708 Pending $365,000 · 2 bd · 2 ba · 1,497 sqft
• 717 lancewood drive, Winter Springs 32708 Pending $359,900 · 3 bd · 2 ba · 1,616 sqft
• 711 andover circle, Winter Springs 32708 Pending $405,000 · 3 bd · 2 ba · 1,545 sqft
• 3880 white birch run, Winter Springs 32708 Pending $263,000 · 3 bd · 3 ba · 1,306 sqft
• 225 spindle palm cove, Winter Springs 32708 Pending $406,990 · 3 bd · 3 ba · 1,476 sqft
• 476 tradition lane, Winter Springs 32708 Pending $280,000 · 3 bd · 3 ba · 1,468 sqft
• 200 west panama road, Winter Springs 32708 Pending $385,000 · 3 bd · 2 ba · 1,528 sqft
• 518 harbor winds court, Winter Springs 32708 Pending $335,000 · 3 bd · 3 ba · 1,680 sqft
• 1625 white dove drive, Winter Springs 32708 Pending $375,000 · 4 bd · 4 ba · 2,306 sqft
• 724 barrington circle, Winter Springs 32708 Active Under Contract $385,000 · 3 bd · 2 ba · 1,450 sqft
• 600 northern way 502, Winter Springs 32708 Active Under Contract $249,900 · 3 bd · 2 ba · 1,425 sqft
• 411 green spring circle, Winter Springs 32708 Active Under Contract $199,900 · 3 bd · 2 ba · 1,130 sqft
• 122 stone gable circle, Winter Springs 32708 Active Under Contract $449,000 · 3 bd · 3 ba · 2,147 sqft
• 140 north fairfax, Winter Springs 32708 Active Under Contract $315,000 · 3 bd · 1 ba · 1,188 sqft
• 4431 brook hollow circle, Winter Springs 32708 Active Under Contract $220,000 · 3 bd · 2 ba · 1,367 sqft
• 471 harbor winds court, Winter Springs 32708 Active Under Contract $325,000 · 3 bd · 3 ba · 1,680 sqft
• 1307 ortega street, Winter Springs 32708 Active Under Contract $400,000 · 3 bd · 2 ba · 1,881 sqft
• 107 golden crest court, Winter Springs 32708 Active Under Contract $479,000 · 3 bd · 2 ba · 1,978 sqft
• 171 constitution way, Winter Springs 32708 Active Under Contract $305,000 · 3 bd · 3 ba · 1,468 sqft
• 239 panorama drive, Winter Springs 32708 Active Under Contract $340,000 · 3 bd · 2 ba · 1,349 sqft
• 120 north fairfax avenue, Winter Springs 32708 Active Under Contract $214,000 · 2 bd · 1 ba · 1,148 sqft
• 560 pleasant grove drive, Winter Springs 32708 Active Under Contract $410,000 · 3 bd · 2 ba · 1,654 sqft
• 807 buckie drive, Winter Springs 32708 Active Under Contract $375,000 · 3 bd · 2 ba · 1,574 sqft
• 439 old farm lane, Winter Springs 32708 Active Under Contract $318,500 · 3 bd · 3 ba · 1,504 sqft
• 440 buckskin court, Winter Springs 32708 Active Under Contract $499,000 · 4 bd · 3 ba · 1,922 sqft
• 4490 brook hollow circle, Winter Springs 32708 Active Under Contract $230,000 · 3 bd · 2 ba · 1,359 sqft
• 629 ryan court, Winter Springs 32708 Active Under Contract $475,000 · 3 bd · 2 ba · 1,857 sqft
• 65 south devon avenue, Winter Springs 32708 Active Under Contract $300,000 · 3 bd · 2 ba · 1,075 sqft
• 143 hayes road, Winter Springs 32708 Active Under Contract $469,000 · 3 bd · 2 ba · 1,649 sqft
• 335 lansbrook lane, Winter Springs 32708 Active Under Contract $323,000 · 2 bd · 2 ba · 1,129 sqft
• 538 crimson lane, Winter Springs 32708 Active Under Contract $369,900 · 3 bd · 4 ba · 1,854 sqft
• 180 constitution way, Winter Springs 32708 Active Under Contract $294,999 · 2 bd · 3 ba · 1,275 sqft
• 907 glen abbey circle, Winter Springs 32708 Active Under Contract $410,000 · 3 bd · 2 ba · 1,791 sqft
• 877 benchwood drive, Winter Springs 32708 Active Under Contract $445,000 · 3 bd · 2 ba · 1,612 sqft
• 603 casa park court g, Winter Springs 32708 Active Under Contract $244,900 · 2 bd · 3 ba · 1,156 sqft
• 504 green spring circle, Winter Springs 32708 Active Under Contract $235,000 · 2 bd · 3 ba · 1,363 sqft
• 1055 chesterfield circle, Winter Springs 32708 Active Under Contract $480,000 · 3 bd · 2 ba · 1,665 sqft
• 472 dewars court, Winter Springs 32708 Active Under Contract $499,900 · 4 bd · 3 ba · 2,222 sqft
• 71 bombay avenue, Winter Springs 32708 Active Under Contract $205,900 · 2 bd · 2 ba · 1,134 sqft
• 1320 spotted sandpiper loop, Winter Springs 32708 Active Under Contract $475,000 · 4 bd · 4 ba · 2,359 sqft
• 240 north devon avenue, Winter Springs 32708 Active Under Contract $355,500 · 3 bd · 2 ba · 1,238 sqft
• 203 sweetgum, Winter Springs 32708 Active Under Contract $399,000 · 3 bd · 2 ba · 1,218 sqft
• 453 gee hammock lane, Winter Springs 32708 Active Under Contract $375,000 · 3 bd · 3 ba · 1,519 sqft
• 740 galloway court, Winter Springs 32708 Active Under Contract $415,000 · 3 bd · 2 ba · 1,692 sqft
• 600 northern way 907, Winter Springs 32708 Active Under Contract $300,000 · 3 bd · 3 ba · 1,447 sqft
• 1153 spotted sandpiper loop, Winter Springs 32708 Active Under Contract $424,990 · 3 bd · 3 ba · 1,768 sqft