Homes under $1M in Winter Park, FL
157 for sale · 591 homes listed · Updated September 27, 2026 · Page 10 of 12
- 722 south ranger boulevard, Winter Park 32792 Off market since Sep 2026 $775,000 · 4 bd · 3 ba · 2,164 sqft
- 252 scottsdale square 252, Winter Park 32792 Off market since Sep 2026 $85,000 · 2 bd · 2 ba · 1,085 sqft
- 2305 sun valley circle, Winter Park 32792 Off market since Sep 2026 $279,900 · 2 bd · 2 ba · 1,295 sqft
- 5184 lazy oaks drive, Winter Park 32792 Off market since Sep 2026 $275,000 · 2 bd · 2 ba · 1,008 sqft
- 1250 south denning drive 109, Winter Park 32789 Off market since Sep 2026 $190,000 · 1 bd · 1 ba · 658 sqft
- 730 west swoope avenue, Winter Park 32789 Off market since Jul 2026 $839,000 · 5 bd · 3 ba · 2,132 sqft
- 3360 royal street, Winter Park 32792 Off market since Jul 2026 $179,900 · 2 bd · 2 ba · 981 sqft
- 2450 grand teton circle 2450, Winter Park 32792 Off market since Sep 2026 $250,000 · 3 bd · 2 ba · 1,311 sqft
- 303 scottsdale square 303, Winter Park 32792 Off market since Sep 2026 $80,000 · 2 bd · 2 ba · 1,020 sqft
- 724 monmouth way, Winter Park 32792 Off market since Sep 2026 $798,000 · 5 bd · 4 ba · 2,832 sqft
- 436 west swoope avenue, Winter Park 32789 Off market since Sep 2026 $699,000 · 4 bd · 4 ba · 2,602 sqft
- 885 carnation drive, Winter Park 32792 Off market since Sep 2026 $368,000 · 4 bd · 2 ba · 1,240 sqft
- 263 scottsdale square 263, Winter Park 32792 Off market since Sep 2026 $80,000 · 2 bd · 2 ba · 1,020 sqft
- 1418 lone feather trail, Winter Park 32792 Off market since Sep 2026 $699,500 · 4 bd · 3 ba · 2,197 sqft
- 1310 fairview avenue, Winter Park 32789 Off market since Aug 2026 $925,000 · 4 bd · 3 ba · 2,552 sqft
- 1401 aster court, Winter Park 32792 Off market since Sep 2026 $414,900 · 4 bd · 2 ba · 1,653 sqft
- 2487 harbour way, Winter Park 32792 Off market since Sep 2026 $270,000 · 3 bd · 3 ba · 1,803 sqft
- 1500 gay road 4d, Winter Park 32789 Off market since Sep 2026 $164,500 · 1 bd · 1 ba · 732 sqft
- 7450 wynnewood square 189, Winter Park 32792 Off market since Sep 2026 $170,000 · 2 bd · 3 ba · 1,031 sqft
- 2526 passamonte drive 10f, Winter Park 32792 Off market since Sep 2026 $335,000 · 3 bd · 3 ba · 1,790 sqft
- 1562 arbor park drive, Winter Park 32789 Off market since Sep 2026 $775,000 · 4 bd · 3 ba · 1,899 sqft
- 2568 lotafun avenue, Winter Park 32789 Off market since Sep 2026 $395,000 · 3 bd · 2 ba · 1,201 sqft
- 1927 south lakemont avenue, Winter Park 32792 Off market since Sep 2026 $925,000 · 3 bd · 4 ba · 2,093 sqft
- 2033 canny cove, Winter Park 32792 Off market since Sep 2026 $389,000 · 3 bd · 3 ba · 1,907 sqft
- 2703 tierra circle, Winter Park 32792 Off market since Sep 2026 $464,000 · 3 bd · 2 ba · 1,737 sqft
- 1850 bryan avenue, Winter Park 32789 Off market since Sep 2026 $729,000 · 3 bd · 2 ba · 1,563 sqft
- 3562 bougainvillea drive, Winter Park 32792 Off market since Sep 2026 $334,000 · 3 bd · 2 ba · 1,149 sqft
- 5409 albert drive, Winter Park 32792 Off market since Sep 2026 $410,000 · 3 bd · 2 ba · 1,483 sqft
- 1000 south semoran boulevard 305, Winter Park 32792 Off market since Sep 2026 $115,000 · 1 bd · 1 ba · 735 sqft
- 1886 clematis lane, Winter Park 32792 Off market since Sep 2026 $425,000 · 3 bd · 2 ba · 1,238 sqft
- 2475 tahoe circle, Winter Park 32792 Off market since Sep 2026 $268,000 · 2 bd · 2 ba · 1,295 sqft
- 3740 hawthorne lane, Winter Park 32792 Off market since Sep 2026 $435,000 · 3 bd · 2 ba · 1,645 sqft
- 405 lake fair lane, Winter Park 32789 Sold on Sep 11, 2026 $434,990 · 3 bd · 2 ba
- 1061 aragon avenue 1061, Winter Park 32789 Off market since Sep 2026 $510,000 · 3 bd · 3 ba · 1,669 sqft
- 1000 south semoran boulevard 302, Winter Park 32792 Off market since Sep 2026 $110,000 · 1 bd · 1 ba · 796 sqft
- 1871 bryan avenue, Winter Park 32789 Off market since Sep 2026 $625,000 · 3 bd · 2 ba · 1,232 sqft
- 2251 nairn drive, Winter Park 32792 Off market since Aug 2026 $625,000 · 4 bd · 3 ba · 1,978 sqft
- 1695 lee road a101, Winter Park 32789 Off market since Sep 2026 $154,900 · 3 bd · 2 ba · 1,149 sqft
- 2007 cornell avenue, Winter Park 32789 Off market since Sep 2026 $449,000 · 3 bd · 2 ba · 1,154 sqft
- 2667 cochise trail, Winter Park 32789 Off market since Sep 2026 $985,000 · 4 bd · 3 ba · 2,868 sqft
- 2017 canny cove, Winter Park 32792 Off market since Sep 2026 $389,900 · 3 bd · 3 ba · 1,907 sqft
- 5210 lazy oaks drive, Winter Park 32792 Off market since Sep 2026 $279,900 · 2 bd · 3 ba · 1,236 sqft
- 4026 tenita drive, Winter Park 32792 Off market since Sep 2026 $599,000 · 3 bd · 2 ba · 2,031 sqft
- 5316 halyard court, Winter Park 32792 Off market since Sep 2026 $495,000 · 3 bd · 2 ba · 1,380 sqft
- 1071 aragon avenue, Winter Park 32789 Off market since Sep 2026 $575,000 · 2 bd · 3 ba · 1,851 sqft
- 7413 belle river court 3, Winter Park 32792 Off market since Sep 2026 $214,900 · 3 bd · 3 ba · 1,151 sqft
- 310 granada drive, Winter Park 32789 Off market since Sep 2026 $339,900 · 3 bd · 2 ba · 1,344 sqft
- 1122 wildmeadow run, Winter Park 32792 Off market since Sep 2026 $665,000 · 4 bd · 3 ba · 1,770 sqft
- 1695 lee road d107, Winter Park 32789 Off market since Sep 2026 $180,000 · 1 bd · 1 ba · 638 sqft
- 283 sandlewood trail 3, Winter Park 32789 Off market since Sep 2026 $285,000 · 2 bd · 3 ba · 960 sqft