Homes under $500K in Winter Park, FL
133 homes for sale · Updated August 12, 2026 · Page 1 of 3
- 1695 lee road c202, Winter Park 32789 $205,000 · 3 bd · 2 ba · 1,149 sqft
- 5331 oak court, Winter Park 32792 $460,000 · 3 bd · 2 ba · 1,263 sqft
- 1849 viburnum lane, Winter Park 32792 $399,900 · 4 bd · 2 ba · 1,627 sqft
- 3019 antique oaks circle 124, Winter Park 32792 $139,500 · 1 bd · 1 ba · 749 sqft
- 311 east morse boulevard 7-11, Winter Park 32789 $279,000 · 1 bd · 1 ba · 570 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 $109,500 · 1 bd · 1 ba · 785 sqft
- 151 north orlando avenue #115, Winter Park 32789 $290,000 · 2 bd · 1 ba · 710 sqft
- 1695 lee road e204, Winter Park 32789 $108,000 · 2 bd · 1 ba · 881 sqft
- 2500 lee road 222, Winter Park 32789 $184,900 · 1 bd · 1 ba · 645 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
- 2651 cayman way, Winter Park 32792 $255,000 · 2 bd · 2 ba · 1,020 sqft
- 311 east morse boulevard 7-19, Winter Park 32789 $284,900 · 1 bd · 1 ba · 482 sqft
- 1052 manchester circle, Winter Park 32792 $460,000 · 3 bd · 2 ba · 1,703 sqft
- 630 killarney bay court 3, Winter Park 32789 $475,000 · 2 bd · 3 ba · 1,428 sqft
- 291 lewfield circle 291, Winter Park 32792 $144,000 · 1 bd · 1 ba · 678 sqft
- 4768 tangerine avenue 4768, Winter Park 32792 $174,900 · 1 bd · 1 ba · 753 sqft
- 1500 gay road 20d, Winter Park 32789 $258,000 · 2 bd · 2 ba · 1,026 sqft
- 604 balfour drive, Winter Park 32792 $430,000 · 4 bd · 2 ba · 1,296 sqft
- 501 heritage boulevard, Winter Park 32792 $449,900 · 4 bd · 2 ba · 1,376 sqft
- 1807 hammerlin avenue g, Winter Park 32789 $499,000 · 3 bd · 3 ba · 1,818 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
- 1695 lee road e103, Winter Park 32789 $129,900 · 2 bd · 1 ba · 881 sqft
- 7393 grand avenue, Winter Park 32792 $325,000 · 3 bd · 2 ba · 1,518 sqft
- 1695 lee road d211, Winter Park 32789 $108,000 · 2 bd · 1 ba · 881 sqft
- 950 hanover avenue, Winter Park 32789 $460,000 · 3 bd · 2 ba · 1,606 sqft
- 5143 lazy oaks drive 5143, Winter Park 32792 $275,000 · 2 bd · 2 ba · 1,008 sqft
- 814 densmore drive, Winter Park 32792 $425,000 · 4 bd · 2 ba · 1,610 sqft
- 2317 sun valley circle 2317, Winter Park 32792 $267,000 · 2 bd · 2 ba · 1,295 sqft
- 2383 sun valley circle 2383, Winter Park 32792 $245,000 · 2 bd · 2 ba · 1,295 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
- 3374 hamlet loop, Winter Park 32792 $360,000 · 3 bd · 3 ba · 1,397 sqft
- 525 ololu drive, Winter Park 32789 $495,900 · 3 bd · 3 ba · 1,786 sqft
- 1695 lee road b210, Winter Park 32789 $89,000 · 1 bd · 1 ba · 638 sqft
- 7327 forest hill court 223, Winter Park 32792 $175,000 · 2 bd · 3 ba · 1,031 sqft
- 5806 marble court, Winter Park 32792 $289,000 · 2 bd · 2 ba · 1,140 sqft
- 2500 lee road 232, Winter Park 32789 $149,000 · 1 bd · 1 ba · 645 sqft
- 440 cambridge boulevard, Winter Park 32789 $369,900 · 2 bd · 1 ba · 988 sqft
- 262 lewfield circle 262, Winter Park 32792 $149,500 · 1 bd · 1 ba · 678 sqft
- 3243 forest oaks court 117, Winter Park 32792 $172,000 · 2 bd · 2 ba · 990 sqft
- 1092 eastbrook boulevard, Winter Park 32792 $399,000 · 3 bd · 2 ba · 1,122 sqft
- 1995 canny cove, Winter Park 32792 $425,000 · 3 bd · 3 ba · 1,907 sqft
- 1500 gay road 17d, Winter Park 32789 $239,500 · 2 bd · 2 ba · 1,026 sqft
- 2503 tahoe circle 2503, Winter Park 32792 $225,000 · 2 bd · 2 ba · 1,173 sqft
- 2512 eastbrook boulevard, Winter Park 32792 $390,000 · 4 bd · 2 ba · 1,607 sqft