Homes under $500K in Winter Park, FL
97 for sale · 367 homes listed · Updated September 27, 2026 · Page 8 of 8
- 2136 linden road, Winter Park 32792 Off market since Sep 2026 $365,000 · 3 bd · 2 ba · 1,185 sqft
- 2302 barbados drive, Winter Park 32792 Off market since Sep 2026 $295,000 · 2 bd · 2 ba · 1,544 sqft
- 7476 woodburn court 38, Winter Park 32792 Off market since Sep 2026 $170,000 · 2 bd · 3 ba · 1,031 sqft
- 2383 sun valley circle 2383, Winter Park 32792 Off market since Sep 2026 $234,900 · 2 bd · 2 ba · 1,295 sqft
- 4870 seminole avenue, Winter Park 32792 Off market since Sep 2026 $380,000 · 3 bd · 2 ba · 1,277 sqft
- 2301 conifer avenue, Winter Park 32792 Off market since Sep 2026 $450,000 · 4 bd · 2 ba · 2,189 sqft
- 7302 swallow run 7302, Winter Park 32792 Off market since Sep 2026 $134,900 · 2 bd · 2 ba · 756 sqft
- 1386 clematis lane, Winter Park 32792 Off market since Sep 2026 $427,000 · 4 bd · 3 ba · 1,714 sqft
- 3334 young street, Winter Park 32792 Off market since Sep 2026 $474,900 · 3 bd · 2 ba · 1,706 sqft
- 5080 seminole avenue, Winter Park 32792 Off market since Sep 2026 $299,900 · 3 bd · 2 ba · 1,078 sqft
- 2463 grand teton circle 2463, Winter Park 32792 Off market since Sep 2026 $249,000 · 3 bd · 3 ba · 1,720 sqft
- 3484 seagrape drive, Winter Park 32792 Off market since Sep 2026 $299,900 · 4 bd · 2 ba · 1,227 sqft
- 7453 daniel webster drive a5, Winter Park 32792 Off market since Sep 2026 $150,000 · 2 bd · 2 ba · 1,063 sqft
- 1306 south pennsylvania avenue 5, Winter Park 32789 Off market since Sep 2026 $359,000 · 2 bd · 1 ba · 830 sqft
- 7348 grand avenue, Winter Park 32792 Off market since Sep 2026 $285,000 · 3 bd · 2 ba · 1,509 sqft
- 602 trinidad court 602, Winter Park 32792 Off market since Sep 2026 $227,000 · 2 bd · 2 ba · 1,120 sqft
- 192 balfour drive 2, Winter Park 32792 Off market since Sep 2026 $319,000 · 2 bd · 2 ba · 1,287 sqft