Homes under $300K in Winter Park, FL
43 for sale · 180 homes listed · Updated September 27, 2026 · Page 4 of 4
- 1695 lee road d107, Winter Park 32789 Off market since Sep 2026 $180,000 · 1 bd · 1 ba · 638 sqft
- 283 sandlewood trail 3, Winter Park 32789 Off market since Sep 2026 $285,000 · 2 bd · 3 ba · 960 sqft
- 3651 north goldenrod road 206, Winter Park 32792 Off market since Sep 2026 $179,900 · 2 bd · 2 ba · 840 sqft
- 2477 tahoe circle 2477, Winter Park 32792 Off market since Sep 2026 $254,000 · 2 bd · 2 ba · 1,316 sqft
- 1250 south denning drive unit 233, Winter Park 32789 Off market since Sep 2026 $245,000 · 2 bd · 2 ba · 913 sqft
- 7468 canford court 24, Winter Park 32792 Off market since Sep 2026 $184,900 · 2 bd · 2 ba · 1,365 sqft
- 3019 antique oaks circle 127, Winter Park 32792 Off market since Sep 2026 $143,500 · 1 bd · 1 ba · 749 sqft
- 623 grenadine court 623, Winter Park 32792 Off market since Sep 2026 $194,900 · 2 bd · 2 ba · 1,037 sqft
- 285 lewfield circle 285, Winter Park 32792 Off market since Sep 2026 $147,000 · 1 bd · 1 ba · 678 sqft
- 151 north orlando avenue 261, Winter Park 32789 Off market since Sep 2026 $219,999 · 1 bd · 1 ba · 582 sqft
- 222 lewfield circle, Winter Park 32792 Off market since Sep 2026 $189,900 · 2 bd · 2 ba · 953 sqft
- 3302 royal street, Winter Park 32792 Off market since Sep 2026 $274,900 · 3 bd · 2 ba · 1,197 sqft
- 151 north orlando avenue 242, Winter Park 32789 Off market since Sep 2026 $269,000 · 2 bd · 1 ba · 710 sqft
- 5108 lazy oaks drive 5108, Winter Park 32792 Off market since Sep 2026 $269,000 · 2 bd · 2 ba · 1,008 sqft
- 3651 north goldenrod road c205, Winter Park 32792 Off market since Sep 2026 $159,900 · 2 bd · 2 ba · 840 sqft
- 2500 lee road 143, Winter Park 32789 Off market since Sep 2026 $130,000 · 1 bd · 1 ba · 645 sqft
- 3020 antique oaks circle 129, Winter Park 32792 Off market since Sep 2026 $135,000 · 2 bd · 2 ba · 1,018 sqft
- 2275 island run, Winter Park 32792 Off market since Sep 2026 $299,990 · 3 bd · 2 ba · 1,467 sqft
- 1250 south denning drive 127, Winter Park 32789 Off market since Sep 2026 $245,000 · 2 bd · 2 ba · 908 sqft
- 3651 north goldenrod road c109, Winter Park 32792 Off market since Sep 2026 $165,000 · 2 bd · 2 ba · 840 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
- 7302 swallow run 7302, Winter Park 32792 Off market since Sep 2026 $134,900 · 2 bd · 2 ba · 756 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
- 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