Homes under $1M in Winter Park, FL
157 for sale · 591 homes listed · Updated September 27, 2026 · Page 12 of 12
- 3020 antique oaks circle 129, Winter Park 32792 Off market since Sep 2026 $135,000 · 2 bd · 2 ba · 1,018 sqft
- 500 north pennsylvania avenue g, Winter Park 32789 Off market since Sep 2026 $349,500 · 2 bd · 1 ba · 709 sqft
- 2122 ridge drive, Winter Park 32792 Off market since Sep 2026 $360,000 · 4 bd · 3 ba · 1,664 sqft
- 2349 shadowland loop, Winter Park 32792 Off market since Sep 2026 $425,000 · 3 bd · 3 ba · 1,755 sqft
- 508 brechin drive, Winter Park 32792 Off market since Sep 2026 $629,000 · 3 bd · 2 ba · 1,783 sqft
- 2275 island run, Winter Park 32792 Off market since Sep 2026 $299,990 · 3 bd · 2 ba · 1,467 sqft
- 2626 ambergate road, Winter Park 32792 Off market since Sep 2026 $380,000 · 3 bd · 1 ba · 1,143 sqft
- 1250 south denning drive 127, Winter Park 32789 Off market since Sep 2026 $245,000 · 2 bd · 2 ba · 908 sqft
- 274 north ranger boulevard, Winter Park 32792 Off market since Sep 2026 $669,900 · 3 bd · 2 ba · 1,420 sqft
- 3651 north goldenrod road c109, Winter Park 32792 Off market since Sep 2026 $165,000 · 2 bd · 2 ba · 840 sqft
- 2136 linden road, Winter Park 32792 Off market since Sep 2026 $365,000 · 3 bd · 2 ba · 1,185 sqft
- 2260 coldstream drive, Winter Park 32792 Off market since Sep 2026 $699,000 · 4 bd · 2 ba · 1,509 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
- 2410 sherbrooke road, Winter Park 32792 Off market since Sep 2026 $789,000 · 4 bd · 3 ba · 2,141 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
- 913 moss lane, Winter Park 32789 Off market since Sep 2026 $950,000 · 3 bd · 2 ba · 1,887 sqft
- 2301 conifer avenue, Winter Park 32792 Off market since Sep 2026 $450,000 · 4 bd · 2 ba · 2,189 sqft
- 447 north phelps avenue, Winter Park 32789 Off market since Sep 2026 $960,000 · 2 bd · 1 ba · 1,290 sqft
- 618 blairshire circle, Winter Park 32792 Off market since Sep 2026 $895,000 · 4 bd · 3 ba · 1,876 sqft
- 7302 swallow run 7302, Winter Park 32792 Off market since Sep 2026 $134,900 · 2 bd · 2 ba · 756 sqft
- 2345 brookshire avenue, Winter Park 32792 Off market since Sep 2026 $850,000 · 3 bd · 3 ba · 2,488 sqft
- 1386 clematis lane, Winter Park 32792 Off market since Sep 2026 $427,000 · 4 bd · 3 ba · 1,714 sqft
- 2215 woodcrest drive, Winter Park 32792 Off market since Sep 2026 $675,000 · 4 bd · 2 ba · 1,688 sqft
- 1421 chestnut avenue, Winter Park 32789 Off market since Sep 2026 $750,000 · 3 bd · 1 ba · 1,325 sqft
- 2572 fifeshire drive, Winter Park 32792 Off market since Sep 2026 $925,000 · 4 bd · 3 ba · 2,578 sqft
- 3334 young street, Winter Park 32792 Off market since Sep 2026 $474,900 · 3 bd · 2 ba · 1,706 sqft
- 250 carolina avenue 202, Winter Park 32789 Off market since Sep 2026 $699,000 · 3 bd · 2 ba · 1,450 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
- 4260 bear gully road, Winter Park 32792 Off market since Sep 2026 $599,000 · 4 bd · 5 ba · 2,322 sqft
- 624 fitzwalter drive, Winter Park 32792 Off market since Sep 2026 $549,000 · 3 bd · 2 ba · 1,335 sqft
- 5303 pine lily circle, Winter Park 32792 Off market since Sep 2026 $659,000 · 3 bd · 2 ba · 2,265 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
- 8113 lazy bear lane, Winter Park 32792 Off market since Sep 2026 $585,000 · 4 bd · 3 ba · 2,267 sqft