Homes under $500K in Winter Park, FL
133 homes for sale · Updated August 12, 2026 · Page 3 of 3
- 2487 harbour way, Winter Park 32792 $290,000 · 3 bd · 3 ba · 1,803 sqft
- 1500 gay road 4d, Winter Park 32789 $169,900 · 1 bd · 1 ba · 732 sqft
- 7450 wynnewood square 189, Winter Park 32792 $185,000 · 2 bd · 3 ba · 1,031 sqft
- 2526 passamonte drive 10f, Winter Park 32792 $335,000 · 3 bd · 3 ba · 1,790 sqft
- 2568 lotafun avenue, Winter Park 32789 $409,900 · 3 bd · 2 ba · 1,201 sqft
- 2033 canny cove, Winter Park 32792 $399,000 · 3 bd · 3 ba · 1,907 sqft
- 7340 daniel webster drive, Winter Park 32792 $179,900 · 3 bd · 2 ba
- 2703 tierra circle, Winter Park 32792 $469,000 · 3 bd · 2 ba · 1,737 sqft
- 2433 grand teton circle, Winter Park 32792 $259,000 · 3 bd · 3 ba · 1,720 sqft
- 200 saint andrews boulevard 2904, Winter Park 32792 $230,000 · 2 bd · 2 ba · 1,219 sqft
- 3562 bougainvillea drive, Winter Park 32792 $339,000 · 3 bd · 2 ba · 1,149 sqft
- 5409 albert drive, Winter Park 32792 $430,000 · 3 bd · 2 ba · 1,483 sqft
- 1000 south semoran boulevard 305, Winter Park 32792 $115,000 · 1 bd · 1 ba · 735 sqft
- 1886 clematis lane, Winter Park 32792 $425,000 · 3 bd · 2 ba · 1,238 sqft
- 2475 tahoe circle, Winter Park 32792 $278,000 · 2 bd · 2 ba · 1,295 sqft
- 3740 hawthorne lane, Winter Park 32792 $435,000 · 3 bd · 2 ba · 1,645 sqft
- 405 lake fair lane, Winter Park 32789 $434,990 · 3 bd · 2 ba
- 1000 south semoran boulevard 302, Winter Park 32792 $115,000 · 1 bd · 1 ba · 796 sqft
- 1695 lee road a101, Winter Park 32789 $154,900 · 3 bd · 2 ba · 1,149 sqft
- 351 starling road, Winter Park 32789 $499,900 · 3 bd · 2 ba · 1,979 sqft
- 2007 cornell avenue, Winter Park 32789 $449,000 · 3 bd · 2 ba · 1,154 sqft
- 7340 swallow run 7340, Winter Park 32792 $145,000 · 2 bd · 2 ba · 802 sqft
- 7261 abbey lane, Winter Park 32792 $350,000 · 3 bd · 2 ba · 1,268 sqft
- 2017 canny cove, Winter Park 32792 $399,900 · 3 bd · 3 ba · 1,907 sqft
- 5210 lazy oaks drive 5210, Winter Park 32792 $289,900 · 2 bd · 3 ba · 1,236 sqft
- 5316 halyard court, Winter Park 32792 $495,000 · 3 bd · 2 ba · 1,380 sqft
- 7413 belle river court 3, Winter Park 32792 $229,900 · 3 bd · 3 ba · 1,151 sqft
- 310 granada drive, Winter Park 32789 $354,999 · 3 bd · 2 ba · 1,344 sqft
- 1695 lee road d107, Winter Park 32789 $180,000 · 1 bd · 1 ba · 638 sqft
- 3328 hamlet loop, Winter Park 32792 $349,900 · 3 bd · 2 ba · 1,397 sqft
- 7487 canford court 5, Winter Park 32792 $249,900 · 2 bd · 3 ba · 1,611 sqft
- 3651 north goldenrod road 206, Winter Park 32792 $179,900 · 2 bd · 2 ba · 840 sqft
- 3651 north goldenrod road a103, Winter Park 32792 $164,900 · 2 bd · 2 ba · 840 sqft