5 Bedroom Homes in Winter Park, FL
37 homes for sale · Updated August 12, 2026
- 1821 englewood road, Winter Park 32789 $3,235,000 · 5 bd · 6 ba · 3,863 sqft
- 207 east kings way, Winter Park 32789 $3,650,000 · 5 bd · 5 ba · 3,719 sqft
- 1885 temple drive, Winter Park 32789 $2,195,000 · 5 bd · 4 ba · 3,691 sqft
- 1523 miller avenue, Winter Park 32789 $1,400,000 · 5 bd · 4 ba · 3,164 sqft
- 40 palmer avenue, Winter Park 32789 $7,250,000 · 5 bd · 6 ba · 5,905 sqft
- 1927 eland avenue, Winter Park 32789 $820,000 · 5 bd · 3 ba · 2,242 sqft
- 2501 winter park road, Winter Park 32789 $1,649,000 · 5 bd · 4 ba · 3,304 sqft
- 914 enclave place, Winter Park 32792 $1,895,000 · 5 bd · 5 ba · 3,617 sqft
- 2702 parkland drive, Winter Park 32789 $1,049,000 · 5 bd · 3 ba · 2,656 sqft
- 2838 wright avenue, Winter Park 32789 $2,399,000 · 5 bd · 5 ba · 3,479 sqft
- 1864 grinnell terrace, Winter Park 32789 $1,599,000 · 5 bd · 4 ba · 3,028 sqft
- 450 lakewood drive, Winter Park 32789 $2,500,000 · 5 bd · 6 ba · 4,572 sqft
- 930 enclave place, Winter Park 32792 $2,050,000 · 5 bd · 5 ba · 3,813 sqft
- 910 enclave place, Winter Park 32792 $1,899,000 · 5 bd · 5 ba · 3,620 sqft
- 1627 mizell avenue, Winter Park 32789 $3,300,000 · 5 bd · 6 ba · 3,421 sqft
- 938 enclave place, Winter Park 32792 $2,099,000 · 5 bd · 5 ba · 3,865 sqft
- 926 enclave place, Winter Park 32792 $2,235,000 · 5 bd · 5 ba · 4,150 sqft
- 1448 lake florence way, Winter Park 32792 $1,099,900 · 5 bd · 5 ba · 3,652 sqft
- 942 enclave place, Winter Park 32792 $2,195,000 · 5 bd · 5 ba · 3,831 sqft
- 950 enclave place, Winter Park 32792 $2,125,000 · 5 bd · 5 ba · 3,797 sqft
- 946 enclave place, Winter Park 32792 $2,175,000 · 5 bd · 5 ba · 3,989 sqft
- 1571 woodland avenue, Winter Park 32789 $6,000,000 · 5 bd · 8 ba · 7,397 sqft
- 2032 kimbrace place, Winter Park 32792 $1,800,000 · 5 bd · 4 ba · 3,382 sqft
- 1473 berkshire avenue, Winter Park 32789 $1,429,000 · 5 bd · 4 ba · 2,351 sqft
- 240 north phelps avenue, Winter Park 32789 $2,150,000 · 5 bd · 5 ba · 2,889 sqft
- 1836 whitehall drive, Winter Park 32789 $3,500,000 · 5 bd · 7 ba · 4,168 sqft
- 1591 cardinal court, Winter Park 32789 $2,995,000 · 5 bd · 3 ba · 3,523 sqft
- 2228 azalea place, Winter Park 32789 $5,600,000 · 5 bd · 6 ba · 5,152 sqft
- 1823 sunset drive, Winter Park 32789 $2,549,000 · 5 bd · 5 ba · 3,479 sqft
- 1180 via lugano, Winter Park 32789 $4,900,000 · 5 bd · 6 ba · 4,961 sqft
- 1754 taylor avenue, Winter Park 32789 $2,569,999 · 5 bd · 5 ba · 3,670 sqft
- 777 halifax avenue, Winter Park 32792 $1,500,000 · 5 bd · 5 ba · 3,109 sqft
- 281 brewer avenue, Winter Park 32789 $1,800,000 · 5 bd · 5 ba · 4,029 sqft
- 1840 laurel road, Winter Park 32789 $2,299,000 · 5 bd · 5 ba · 2,868 sqft
- 1525 granville drive, Winter Park 32789 $4,750,000 · 5 bd · 6 ba · 5,211 sqft
- 1901 loch berry road, Winter Park 32792 $3,500,000 · 5 bd · 6 ba · 4,831 sqft
- 857 brock street, Winter Park 32789 $4,650,000 · 5 bd · 6 ba · 4,827 sqft