Homes under $1M in Winter Park, FL
226 for sale · 436 homes listed · Updated September 25, 2026 · Page 1 of 9
- 1695 lee road c202, Winter Park 32789 $205,000 · 3 bd · 2 ba · 1,149 sqft
- 3071 george mason avenue 5, Winter Park 32792 $89,900 · 1 bd · 1 ba · 549 sqft
- 151 north orlando avenue 118, Winter Park 32789 $299,999 · 2 bd · 1 ba · 710 sqft
- 3370 cedar springs place 156, Winter Park 32792 $182,500 · 2 bd · 3 ba · 1,031 sqft
- 5331 oak court, Winter Park 32792 $460,000 · 3 bd · 2 ba · 1,263 sqft
- 2758 banchory road, Winter Park 32792 $639,000 · 3 bd · 3 ba · 1,539 sqft
- 1849 viburnum lane, Winter Park 32792 $399,900 · 4 bd · 2 ba · 1,627 sqft
- 2948 antique oaks circle 94, Winter Park 32792 $150,000 · 1 bd · 1 ba · 749 sqft
- 2336 sun valley circle bldg 20, Winter Park 32792 $285,000 · 2 bd · 2 ba · 1,669 sqft
- 7471 canford court 19, Winter Park 32792 $199,000 · 2 bd · 2 ba · 1,393 sqft
- 311 scottsdale square 311, Winter Park 32792 $109,400 · 1 bd · 1 ba · 785 sqft
- 2612 roxbury road, Winter Park 32789 $629,900 · 5 bd · 3 ba · 2,472 sqft
- 151 north orlando avenue #115, Winter Park 32789 $285,000 · 2 bd · 1 ba · 710 sqft
- 560 ololu drive, Winter Park 32789 $899,000 · 2 bd · 2 ba · 1,086 sqft
- 2217 sussex road, Winter Park 32792 $485,000 · 4 bd · 2 ba · 2,092 sqft
- 2500 lee road 222, Winter Park 32789 $184,400 · 1 bd · 1 ba · 645 sqft
- 230 strathy lane, Winter Park 32792 $499,000 · 2 bd · 1 ba · 920 sqft
- 2231 nairn drive, Winter Park 32792 $499,000 · 3 bd · 2 ba · 1,088 sqft
- 205 lewfield circle 205, Winter Park 32792 $182,900 · 2 bd · 2 ba · 927 sqft
- 3220 netherwood drive, Winter Park 32792 $268,950 · 2 bd · 2 ba · 1,036 sqft
- 432 west swoope avenue, Winter Park 32789 $680,000 · 4 bd · 4 ba · 2,664 sqft
- 330 elkhorn court, Winter Park 32792 $544,900 · 3 bd · 2 ba · 1,570 sqft
- 1521 heron wood place, Winter Park 32792 $829,500 · 4 bd · 2 ba · 3,950 sqft
- 1927 eland avenue, Winter Park 32789 $820,000 · 5 bd · 3 ba · 2,242 sqft
- 2708 lion heart road, Winter Park 32792 $614,500 · 3 bd · 2 ba · 1,785 sqft
- 1354 indiana avenue, Winter Park 32789 $574,900 · 3 bd · 2 ba · 1,269 sqft
- 2918 antique oaks circle 25, Winter Park 32792 $189,000 · 2 bd · 2 ba · 1,018 sqft
- lot #21 karolina avenue, Winter Park 32789 $918,000 · 4 bd · 3 ba · 2,662 sqft
- 501 heritage boulevard, Winter Park 32792 $426,000 · 4 bd · 2 ba · 1,376 sqft
- 3027 aaron burr avenue l1, Winter Park 32792 $159,000 · 2 bd · 3 ba · 1,090 sqft
- 7300 daniel webster drive m7, Winter Park 32792 $159,000 · 2 bd · 3 ba · 1,108 sqft
- 1131 wildmeadow run, Winter Park 32792 $825,000 · 4 bd · 4 ba · 2,589 sqft
- 1090 wildmeadow run, Winter Park 32792 $835,000 · 4 bd · 4 ba · 2,589 sqft
- 7393 grand avenue, Winter Park 32792 $325,000 · 3 bd · 2 ba · 1,518 sqft
- 1369 blue stem lane, Winter Park 32792 $775,000 · 4 bd · 4 ba · 2,589 sqft
- 1695 lee road d211, Winter Park 32789 $107,000 · 2 bd · 1 ba · 881 sqft
- 2600 euston road, Winter Park 32789 $630,000 · 6 bd · 3 ba · 3,145 sqft
- 950 hanover avenue, Winter Park 32789 $439,000 · 3 bd · 2 ba · 1,606 sqft
- 5143 lazy oaks drive 5143, Winter Park 32792 $275,000 · 2 bd · 2 ba · 1,008 sqft
- 1741 westchester avenue, Winter Park 32789 $529,000 · 3 bd · 2 ba · 1,434 sqft
- 2317 sun valley circle 2317, Winter Park 32792 $267,000 · 2 bd · 2 ba · 1,295 sqft
- 7641 village green drive, Winter Park 32792 $539,000 · 3 bd · 3 ba · 1,602 sqft
- 1319 bessmor road, Winter Park 32789 $589,000 · 3 bd · 2 ba · 1,126 sqft
- 7429 daniel webster drive 14 #c, Winter Park 32792 $133,000 · 2 bd · 2 ba · 1,036 sqft
- 3440 allston lane, Winter Park 32792 $405,000 · 3 bd · 3 ba · 1,533 sqft
- 1611 chestnut avenue, Winter Park 32789 $995,000 · 4 bd · 4 ba · 2,916 sqft
- 525 ololu drive, Winter Park 32789 $490,900 · 3 bd · 3 ba · 1,786 sqft
- 7327 forest hill court 223, Winter Park 32792 $175,000 · 2 bd · 3 ba · 1,031 sqft
- 3243 forest oaks court 117, Winter Park 32792 $172,000 · 2 bd · 2 ba · 990 sqft
- 1092 eastbrook boulevard, Winter Park 32792 $390,000 · 3 bd · 2 ba · 1,122 sqft