Homes under $1M in Winter Park, FL
157 for sale · 591 homes listed · Updated September 27, 2026 · Page 3 of 12
- 3209 heartwood avenue, Winter Park 32792 $449,900 · 4 bd · 2 ba · 1,627 sqft
- 2007 cornell avenue, Winter Park 32789 $449,000 · 3 bd · 2 ba · 1,154 sqft
- 7525 lodge pole trail, Winter Park 32792 $575,000 · 4 bd · 2 ba · 1,936 sqft
- 338 blue heron drive, Winter Park 32789 $836,000 · 3 bd · 3 ba · 2,017 sqft
- 1250 formosa avenue, Winter Park 32789 $535,000 · 3 bd · 4 ba · 1,937 sqft
- 7450 wynnewood square #189, Winter Park 32792 $170,000 · 2 bd · 3 ba · 1,031 sqft
- 1500 gay road #4d, Winter Park 32789 $164,500 · 1 bd · 1 ba · 732 sqft
- 1849 viburnum lane, Winter Park 32792 $389,900 · 4 bd · 2 ba · 1,627 sqft
- 618 blairshire circle, Winter Park 32792 $895,000 · 4 bd · 3 ba · 1,876 sqft
- 3370 cedar springs place #156, Winter Park 32792 $179,990 · 2 bd · 3 ba · 1,031 sqft
- 192 balfour drive #2, Winter Park 32792 $319,000 · 2 bd · 2 ba · 1,287 sqft
- 2122 ridge drive, Winter Park 32792 $360,000 · 4 bd · 3 ba · 1,664 sqft
- 2008 houndslake drive, Winter Park 32792 $475,000 · 4 bd · 2 ba · 2,250 sqft
- 2211 king richards court, Winter Park 32792 $529,000 · 4 bd · 2 ba · 1,845 sqft
- 2345 brookshire avenue, Winter Park 32792 $850,000 · 3 bd · 3 ba · 2,488 sqft
- 1265 arlington place, Winter Park 32789 $810,000 · 3 bd · 4 ba · 2,030 sqft
- 259 orange terrace drive, Winter Park 32789 $449,900 · 3 bd · 2 ba · 1,248 sqft
- 2305 sun valley circle, Winter Park 32792 $279,900 · 2 bd · 2 ba · 1,295 sqft
- 2215 woodcrest drive, Winter Park 32792 $675,000 · 4 bd · 2 ba · 1,688 sqft
- 4870 seminole avenue, Winter Park 32792 $380,000 · 3 bd · 2 ba · 1,277 sqft
- 250 carolina avenue #202, Winter Park 32789 $699,000 · 3 bd · 2 ba · 1,450 sqft
- 5303 pine lily circle, Winter Park 32792 $659,000 · 3 bd · 2 ba · 2,265 sqft
- 1256 south pennsylvania avenue #9, Winter Park 32789 $950,000 · 3 bd · 3 ba · 1,957 sqft
- 950 hanover avenue, Winter Park 32789 $439,000 · 3 bd · 2 ba · 1,606 sqft
- 2475 tahoe circle, Winter Park 32792 $268,000 · 2 bd · 2 ba · 1,295 sqft
- 1259 indiana avenue, Winter Park 32789 $575,000 · 2 bd · 3 ba · 1,648 sqft
- 2818 ambergate road, Winter Park 32792 $429,900 · 3 bd · 2 ba · 1,398 sqft
- 739 roughbeard road, Winter Park 32792 $780,000 · 5 bd · 3 ba · 2,194 sqft
- 1660 orange avenue, Winter Park 32789 $479,900 · 3 bd · 2 ba · 1,614 sqft
- 1211 schultz avenue, Winter Park 32789 $475,000 · 3 bd · 2 ba · 1,085 sqft
- 1250 south denning drive #119, Winter Park 32789 $265,000 · 2 bd · 2 ba · 908 sqft
- 1000 south semoran boulevard #408, Winter Park 32792 $138,000 · 1 bd · 1 ba · 776 sqft
- 1000 south semoran boulevard #306, Winter Park 32792 $138,000 · 1 bd · 1 ba · 796 sqft
- 1000 south semoran boulevard #404, Winter Park 32792 $138,000 · 1 bd · 1 ba · 776 sqft
- 7522 aloma pines court, Winter Park 32792 $375,000 · 3 bd · 3 ba · 1,872 sqft
- 2612 roxbury road, Winter Park 32789 $605,000 · 5 bd · 3 ba · 2,472 sqft
- 2054 eastbrook boulevard, Winter Park 32792 $500,000 · 4 bd · 3 ba · 2,031 sqft
- 7393 grand avenue, Winter Park 32792 $325,000 · 3 bd · 2 ba · 1,518 sqft
- 7506 cranes creek court #30, Winter Park 32792 $365,000 · 3 bd · 3 ba · 1,861 sqft
- 5331 oak court, Winter Park 32792 $460,000 · 3 bd · 2 ba · 1,263 sqft
- 2923 antique oaks circle #34, Winter Park 32792 $180,000 · 2 bd · 2 ba · 1,105 sqft
- 885 carnation drive, Winter Park 32792 $368,000 · 4 bd · 2 ba · 1,240 sqft
- 5503 albert drive, Winter Park 32792 $399,900 · 3 bd · 2 ba · 1,366 sqft
- 310 granada drive, Winter Park 32789 $339,900 · 3 bd · 2 ba · 1,344 sqft
- 2568 lotafun avenue, Winter Park 32789 $395,000 · 3 bd · 2 ba · 1,201 sqft
- 205 lewfield circle #205, Winter Park 32792 $182,900 · 2 bd · 2 ba · 927 sqft
- 525 ololu drive, Winter Park 32789 $490,900 · 3 bd · 3 ba · 1,786 sqft
- 700 melrose avenue #j24, Winter Park 32789 $350,000 · 1 bd · 1 ba · 987 sqft
- 501 heritage boulevard, Winter Park 32792 $419,000 · 4 bd · 2 ba · 1,376 sqft
- 4353 steed terrace, Winter Park 32792 $599,900 · 4 bd · 2 ba · 2,275 sqft