Homes under $500K in Winter Park, FL
141 for sale · 271 homes listed · Updated September 27, 2026 · Page 1 of 6
- 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
- 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
- 151 north orlando avenue #115, Winter Park 32789 $285,000 · 2 bd · 1 ba · 710 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
- 2918 antique oaks circle 25, Winter Park 32792 $189,000 · 2 bd · 2 ba · 1,018 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
- 7393 grand avenue, Winter Park 32792 $325,000 · 3 bd · 2 ba · 1,518 sqft
- 1695 lee road d211, Winter Park 32789 $107,000 · 2 bd · 1 ba · 881 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
- 2317 sun valley circle 2317, Winter Park 32792 $267,000 · 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
- 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
- 1995 canny cove, Winter Park 32792 $399,000 · 3 bd · 3 ba · 1,907 sqft
- 2512 eastbrook boulevard, Winter Park 32792 $390,000 · 4 bd · 2 ba · 1,607 sqft
- 2923 antique oaks circle 34, Winter Park 32792 $180,000 · 2 bd · 2 ba · 1,105 sqft
- 700 melrose avenue j24, Winter Park 32789 $350,000 · 1 bd · 1 ba · 987 sqft
- 7522 aloma pines court, Winter Park 32792 $375,000 · 3 bd · 3 ba · 1,872 sqft
- 193 lewfield circle, Winter Park 32792 $248,900 · 2 bd · 3 ba · 1,300 sqft
- 316 beckett court, Winter Park 32792 $450,000 · 4 bd · 2 ba · 1,651 sqft
- 1320 gladiolas drive, Winter Park 32792 $469,900 · 4 bd · 2 ba · 1,624 sqft
- 1840 aster drive, Winter Park 32792 $389,950 · 3 bd · 2 ba · 1,667 sqft
- 5503 albert drive, Winter Park 32792 $399,900 · 3 bd · 2 ba · 1,366 sqft
- 2715 prince john road, Winter Park 32792 $494,900 · 3 bd · 2 ba · 1,565 sqft
- 2500 lee road 220, Winter Park 32789 $199,900 · 2 bd · 1 ba · 851 sqft
- 151 north orlando avenue 142, Winter Park 32789 $199,900 · 1 bd · 1 ba · 582 sqft
- 1535 lawndale circle, Winter Park 32792 $425,000 · 3 bd · 2 ba · 1,676 sqft
- 8433 commander cove, Winter Park 32792 $455,000 · 4 bd · 3 ba · 1,903 sqft
- 2008 houndslake drive, Winter Park 32792 $475,000 · 4 bd · 2 ba · 2,250 sqft
- 1605 puritan avenue, Winter Park 32792 $379,000 · 3 bd · 2 ba · 1,285 sqft
- 1500 gay road 3c, Winter Park 32789 $235,000 · 2 bd · 2 ba · 1,026 sqft