Homes under $500K in Winter Park, FL
97 for sale · 367 homes listed · Updated September 27, 2026 · Page 5 of 8
- 3370 cedar springs place 156, Winter Park 32792 Off market since Sep 2026 $179,990 · 2 bd · 3 ba · 1,031 sqft
- 5331 oak court, Winter Park 32792 Off market since Sep 2026 $460,000 · 3 bd · 2 ba · 1,263 sqft
- 240 orange terrace drive, Winter Park 32789 Off market since Jul 2026 $470,000 · 4 bd · 2 ba · 1,718 sqft
- 1849 viburnum lane, Winter Park 32792 Off market since Sep 2026 $389,900 · 4 bd · 2 ba · 1,627 sqft
- 2948 antique oaks circle 94, Winter Park 32792 Off market since Sep 2026 $150,000 · 1 bd · 1 ba · 749 sqft
- 346 south ranger boulevard, Winter Park 32792 Off market since Aug 2026 $475,000 · 3 bd · 2 ba · 1,592 sqft
- 2336 sun valley circle bldg 20, Winter Park 32792 Off market since Sep 2026 $285,000 · 2 bd · 2 ba · 1,669 sqft
- 7471 canford court 19, Winter Park 32792 Off market since Sep 2026 $199,000 · 2 bd · 2 ba · 1,393 sqft
- 311 scottsdale square 311, Winter Park 32792 Off market since Sep 2026 $109,400 · 1 bd · 1 ba · 785 sqft
- 7470 canford court 23, Winter Park 32792 Off market since Jul 2026 $245,900 · 3 bd · 3 ba · 1,580 sqft
- 151 north orlando avenue #115, Winter Park 32789 Off market since Sep 2026 $285,000 · 2 bd · 1 ba · 710 sqft
- 2217 sussex road, Winter Park 32792 Off market since Sep 2026 $485,000 · 4 bd · 2 ba · 2,092 sqft
- 2500 lee road 222, Winter Park 32789 Off market since Sep 2026 $184,400 · 1 bd · 1 ba · 645 sqft
- 230 strathy lane, Winter Park 32792 Off market since Sep 2026 $499,000 · 2 bd · 1 ba · 920 sqft
- 2231 nairn drive, Winter Park 32792 Off market since Sep 2026 $499,000 · 3 bd · 2 ba · 1,088 sqft
- 205 lewfield circle 205, Winter Park 32792 Off market since Sep 2026 $182,900 · 2 bd · 2 ba · 927 sqft
- 3220 netherwood drive, Winter Park 32792 Off market since Sep 2026 $268,950 · 2 bd · 2 ba · 1,036 sqft
- 311 east morse boulevard 7-19, Winter Park 32789 Off market since Aug 2026 $284,900 · 1 bd · 1 ba · 482 sqft
- 1052 manchester circle, Winter Park 32792 Off market since Sep 2026 $460,000 · 3 bd · 2 ba · 1,703 sqft
- 1000 south semoran boulevard 715, Winter Park 32792 Off market since Jul 2026 $122,990 · 1 bd · 1 ba · 735 sqft
- 4768 tangerine avenue 4768, Winter Park 32792 Off market since Sep 2026 $174,900 · 1 bd · 1 ba · 753 sqft
- 2648 galliano circle, Winter Park 32792 Off market since Jul 2026 $355,000 · 2 bd · 3 ba · 1,550 sqft
- 277 scottsdale square 277, Winter Park 32792 Off market since Sep 2026 $99,000 · 2 bd · 2 ba · 1,020 sqft
- 2918 antique oaks circle 25, Winter Park 32792 Off market since Sep 2026 $189,000 · 2 bd · 2 ba · 1,018 sqft
- 604 balfour drive, Winter Park 32792 Off market since Sep 2026 $430,000 · 4 bd · 2 ba · 1,296 sqft
- 501 heritage boulevard, Winter Park 32792 Off market since Sep 2026 $419,000 · 4 bd · 2 ba · 1,376 sqft
- 3027 aaron burr avenue l1, Winter Park 32792 Off market since Sep 2026 $159,000 · 2 bd · 3 ba · 1,090 sqft
- 7300 daniel webster drive m7, Winter Park 32792 Off market since Sep 2026 $159,000 · 2 bd · 3 ba · 1,108 sqft
- 1695 lee road e103, Winter Park 32789 Off market since Aug 2026 $129,900 · 2 bd · 1 ba · 881 sqft
- 7393 grand avenue, Winter Park 32792 Off market since Sep 2026 $325,000 · 3 bd · 2 ba · 1,518 sqft
- 1695 lee road d211, Winter Park 32789 Off market since Sep 2026 $107,000 · 2 bd · 1 ba · 881 sqft
- 950 hanover avenue, Winter Park 32789 Off market since Sep 2026 $439,000 · 3 bd · 2 ba · 1,606 sqft
- 3021 aaron burr avenue 3, Winter Park 32792 Off market since Jul 2026 $140,000 · 2 bd · 3 ba · 1,090 sqft
- 5143 lazy oaks drive 5143, Winter Park 32792 Off market since Sep 2026 $275,000 · 2 bd · 2 ba · 1,008 sqft
- 814 densmore drive, Winter Park 32792 Off market since Sep 2026 $425,000 · 4 bd · 2 ba · 1,610 sqft
- 811 overspin drive, Winter Park 32789 Off market since Jul 2026 $349,000 · 2 bd · 1 ba · 749 sqft
- 2317 sun valley circle 2317, Winter Park 32792 Off market since Sep 2026 $267,000 · 2 bd · 2 ba · 1,295 sqft
- 2383 sun valley circle 2383, Winter Park 32792 Off market since Sep 2026 $245,000 · 2 bd · 2 ba · 1,295 sqft
- 3440 allston lane, Winter Park 32792 Off market since Sep 2026 $405,000 · 3 bd · 3 ba · 1,533 sqft
- 7484 canford court 8, Winter Park 32792 Off market since Jul 2026 $240,000 · 3 bd · 3 ba · 1,578 sqft
- 525 ololu drive, Winter Park 32789 Off market since Sep 2026 $490,900 · 3 bd · 3 ba · 1,786 sqft
- 7327 forest hill court 223, Winter Park 32792 Off market since Sep 2026 $175,000 · 2 bd · 3 ba · 1,031 sqft
- 5806 marble court, Winter Park 32792 Off market since Aug 2026 $289,000 · 2 bd · 2 ba · 1,140 sqft
- 262 lewfield circle 262, Winter Park 32792 Off market since Sep 2026 $149,500 · 1 bd · 1 ba · 678 sqft
- 3243 forest oaks court 117, Winter Park 32792 Off market since Sep 2026 $172,000 · 2 bd · 2 ba · 990 sqft
- 1092 eastbrook boulevard, Winter Park 32792 Off market since Sep 2026 $390,000 · 3 bd · 2 ba · 1,122 sqft
- 1995 canny cove, Winter Park 32792 Off market since Sep 2026 $399,000 · 3 bd · 3 ba · 1,907 sqft
- 2503 tahoe circle 2503, Winter Park 32792 Off market since Sep 2026 $225,000 · 2 bd · 2 ba · 1,173 sqft
- 2512 eastbrook boulevard, Winter Park 32792 Off market since Sep 2026 $390,000 · 4 bd · 2 ba · 1,607 sqft
- 2923 antique oaks circle 34, Winter Park 32792 Off market since Sep 2026 $180,000 · 2 bd · 2 ba · 1,105 sqft