Homes under $300K in Winter Park, FL
43 for sale · 180 homes listed · Updated September 27, 2026 · Page 3 of 4
- 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
- 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
- 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
- 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
- 2503 tahoe circle 2503, Winter Park 32792 Off market since Sep 2026 $225,000 · 2 bd · 2 ba · 1,173 sqft
- 2923 antique oaks circle 34, Winter Park 32792 Off market since Sep 2026 $180,000 · 2 bd · 2 ba · 1,105 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
- 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
- 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
- 2450 grand teton circle 2450, Winter Park 32792 Off market since Sep 2026 $250,000 · 3 bd · 2 ba · 1,311 sqft
- 303 scottsdale square 303, Winter Park 32792 Off market since Sep 2026 $80,000 · 2 bd · 2 ba · 1,020 sqft
- 263 scottsdale square 263, Winter Park 32792 Off market since Sep 2026 $80,000 · 2 bd · 2 ba · 1,020 sqft
- 2487 harbour way, Winter Park 32792 Off market since Sep 2026 $270,000 · 3 bd · 3 ba · 1,803 sqft
- 1500 gay road 4d, Winter Park 32789 Off market since Sep 2026 $164,500 · 1 bd · 1 ba · 732 sqft
- 7450 wynnewood square 189, Winter Park 32792 Off market since Sep 2026 $170,000 · 2 bd · 3 ba · 1,031 sqft
- 1000 south semoran boulevard 305, Winter Park 32792 Off market since Sep 2026 $115,000 · 1 bd · 1 ba · 735 sqft
- 2475 tahoe circle, Winter Park 32792 Off market since Sep 2026 $268,000 · 2 bd · 2 ba · 1,295 sqft
- 1000 south semoran boulevard 302, Winter Park 32792 Off market since Sep 2026 $110,000 · 1 bd · 1 ba · 796 sqft
- 1695 lee road a101, Winter Park 32789 Off market since Sep 2026 $154,900 · 3 bd · 2 ba · 1,149 sqft
- 5210 lazy oaks drive, Winter Park 32792 Off market since Sep 2026 $279,900 · 2 bd · 3 ba · 1,236 sqft
- 7413 belle river court 3, Winter Park 32792 Off market since Sep 2026 $214,900 · 3 bd · 3 ba · 1,151 sqft