Homes under $400K in Winter Park, FL
66 for sale · 260 homes listed · Updated September 27, 2026 · Page 4 of 6
- 311 east morse boulevard 7-19, Winter Park 32789 Off market since Aug 2026 $284,900 · 1 bd · 1 ba · 482 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
- 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
- 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
- 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
- 7484 canford court 8, Winter Park 32792 Off market since Jul 2026 $240,000 · 3 bd · 3 ba · 1,578 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
- 700 melrose avenue j24, Winter Park 32789 Off market since Sep 2026 $350,000 · 1 bd · 1 ba · 987 sqft
- 7522 aloma pines court, Winter Park 32792 Off market since Sep 2026 $375,000 · 3 bd · 3 ba · 1,872 sqft
- 193 lewfield circle, Winter Park 32792 Off market since Sep 2026 $248,900 · 2 bd · 3 ba · 1,300 sqft
- 200 saint andrews boulevard 704, Winter Park 32792 Off market since Sep 2026 $164,999 · 1 bd · 1 ba · 793 sqft
- 1840 aster drive, Winter Park 32792 Off market since Sep 2026 $389,950 · 3 bd · 2 ba · 1,667 sqft
- 5503 albert drive, Winter Park 32792 Off market since Sep 2026 $399,900 · 3 bd · 2 ba · 1,366 sqft
- 2500 lee road 220, Winter Park 32789 Off market since Sep 2026 $199,900 · 2 bd · 1 ba · 851 sqft
- 151 north orlando avenue 142, Winter Park 32789 Off market since Sep 2026 $199,900 · 1 bd · 1 ba · 582 sqft
- 1605 puritan avenue, Winter Park 32792 Off market since Sep 2026 $379,000 · 3 bd · 2 ba · 1,285 sqft
- 4756 tangerine avenue 4756, Winter Park 32792 Off market since Sep 2026 $185,000 · 2 bd · 2 ba · 1,058 sqft
- 1500 gay road 3c, Winter Park 32789 Off market since Sep 2026 $235,000 · 2 bd · 2 ba · 1,026 sqft
- 2339 inagua way, Winter Park 32792 Off market since Sep 2026 $296,500 · 3 bd · 2 ba · 1,324 sqft
- 7733 country place g2, Winter Park 32792 Off market since Aug 2026 $229,500 · 2 bd · 2 ba · 1,068 sqft
- 2712 tortoise cove, Winter Park 32792 Off market since Sep 2026 $235,000 · 2 bd · 1 ba · 924 sqft
- 7488 whisperwood drive 28, Winter Park 32792 Off market since Sep 2026 $199,000 · 2 bd · 3 ba · 1,578 sqft
- 1000 south semoran boulevard 306, Winter Park 32792 Off market since Sep 2026 $138,000 · 1 bd · 1 ba · 796 sqft
- 1000 south semoran boulevard 408, Winter Park 32792 Off market since Sep 2026 $138,000 · 1 bd · 1 ba · 776 sqft
- 1000 south semoran boulevard 404, Winter Park 32792 Off market since Sep 2026 $138,000 · 1 bd · 1 ba · 776 sqft
- 2372 sun valley circle 2372, Winter Park 32792 Off market since Sep 2026 $285,000 · 2 bd · 2 ba · 1,495 sqft
- 252 scottsdale square 252, Winter Park 32792 Off market since Sep 2026 $85,000 · 2 bd · 2 ba · 1,085 sqft
- 2305 sun valley circle, Winter Park 32792 Off market since Sep 2026 $279,900 · 2 bd · 2 ba · 1,295 sqft
- 5184 lazy oaks drive, Winter Park 32792 Off market since Sep 2026 $275,000 · 2 bd · 2 ba · 1,008 sqft
- 1250 south denning drive 109, Winter Park 32789 Off market since Sep 2026 $190,000 · 1 bd · 1 ba · 658 sqft
- 3360 royal street, Winter Park 32792 Off market since Jul 2026 $179,900 · 2 bd · 2 ba · 981 sqft