5 Bedroom Homes in Winter Park, FL
33 for sale · 106 homes listed · Updated September 27, 2026 · Page 2 of 3
- 1523 miller avenue, Winter Park 32789 Off market since Sep 2026 $1,399,000 · 5 bd · 4 ba · 3,164 sqft
- 40 palmer avenue, Winter Park 32789 Off market since Sep 2026 $7,250,000 · 5 bd · 6 ba · 5,905 sqft
- 1927 eland avenue, Winter Park 32789 Off market since Sep 2026 $820,000 · 5 bd · 3 ba · 2,242 sqft
- 1200 via salerno, Winter Park 32789 Off market since Jul 2026 $5,995,000 · 5 bd · 6 ba · 5,476 sqft
- 609 south phelps avenue, Winter Park 32789 Off market since Jul 2026 $2,829,000 · 5 bd · 5 ba · 4,018 sqft
- 914 enclave place, Winter Park 32792 Off market since Sep 2026 $2,070,000 · 5 bd · 5 ba · 3,617 sqft
- 2702 parkland drive, Winter Park 32789 Off market since Sep 2026 $1,049,000 · 5 bd · 3 ba · 2,656 sqft
- 2838 wright avenue, Winter Park 32789 Off market since Sep 2026 $2,399,000 · 5 bd · 5 ba · 3,479 sqft
- 1864 grinnell terrace, Winter Park 32789 Off market since Sep 2026 $1,599,000 · 5 bd · 4 ba · 3,028 sqft
- 450 lakewood drive, Winter Park 32789 Off market since Sep 2026 $2,500,000 · 5 bd · 6 ba · 4,572 sqft
- 739 roughbeard road, Winter Park 32792 Off market since Jul 2026 $780,000 · 5 bd · 3 ba · 2,194 sqft
- 141 west lake sue avenue, Winter Park 32789 Off market since Jul 2026 $4,200,000 · 5 bd · 7 ba · 5,500 sqft
- 930 enclave place, Winter Park 32792 Off market since Sep 2026 $2,275,000 · 5 bd · 5 ba · 3,813 sqft
- 910 enclave place, Winter Park 32792 Off market since Sep 2026 $1,899,000 · 5 bd · 5 ba · 3,620 sqft
- 1627 mizell avenue, Winter Park 32789 Off market since Sep 2026 $3,300,000 · 5 bd · 6 ba · 3,421 sqft
- 938 enclave place, Winter Park 32792 Off market since Sep 2026 $2,300,000 · 5 bd · 5 ba · 3,865 sqft
- 926 enclave place, Winter Park 32792 Off market since Sep 2026 $2,475,000 · 5 bd · 5 ba · 4,150 sqft
- 1448 lake florence way, Winter Park 32792 Off market since Sep 2026 $1,049,900 · 5 bd · 5 ba · 3,652 sqft
- 942 enclave place, Winter Park 32792 Off market since Sep 2026 $2,195,000 · 5 bd · 5 ba · 3,831 sqft
- 950 enclave place, Winter Park 32792 Off market since Sep 2026 $2,125,000 · 5 bd · 5 ba · 3,797 sqft
- 946 enclave place, Winter Park 32792 Off market since Sep 2026 $2,375,000 · 5 bd · 5 ba · 3,989 sqft
- 1571 woodland avenue, Winter Park 32789 Off market since Sep 2026 $6,000,000 · 5 bd · 8 ba · 7,397 sqft
- 2032 kimbrace place, Winter Park 32792 Off market since Sep 2026 $1,800,000 · 5 bd · 4 ba · 3,382 sqft
- 1473 berkshire avenue, Winter Park 32789 Off market since Sep 2026 $1,369,000 · 5 bd · 4 ba · 2,351 sqft
- 240 north phelps avenue, Winter Park 32789 Off market since Sep 2026 $2,050,000 · 5 bd · 5 ba · 2,889 sqft
- 121 east fawsett road, Winter Park 32789 Off market since Jul 2026 $3,490,000 · 5 bd · 6 ba · 4,191 sqft
- 1600 legion drive, Winter Park 32789 Off market since Aug 2026 $3,795,000 · 5 bd · 6 ba · 4,483 sqft
- 1836 whitehall drive, Winter Park 32789 Off market since Sep 2026 $2,995,000 · 5 bd · 7 ba · 4,168 sqft
- 2228 azalea place, Winter Park 32789 Off market since Sep 2026 $5,600,000 · 5 bd · 6 ba · 5,152 sqft
- 730 west swoope avenue, Winter Park 32789 Off market since Jul 2026 $839,000 · 5 bd · 3 ba · 2,132 sqft
- 1823 sunset drive, Winter Park 32789 Off market since Sep 2026 $2,549,000 · 5 bd · 5 ba · 3,479 sqft
- 1754 taylor avenue, Winter Park 32789 Off market since Sep 2026 $2,569,999 · 5 bd · 5 ba · 3,670 sqft
- 777 halifax avenue, Winter Park 32792 Off market since Sep 2026 $1,449,000 · 5 bd · 5 ba · 3,109 sqft
- 724 monmouth way, Winter Park 32792 Off market since Sep 2026 $798,000 · 5 bd · 4 ba · 2,832 sqft
- 281 brewer avenue, Winter Park 32789 Off market since Sep 2026 $1,800,000 · 5 bd · 5 ba · 4,029 sqft
- 1840 laurel road, Winter Park 32789 Off market since Sep 2026 $2,299,000 · 5 bd · 5 ba · 2,868 sqft
- 1525 granville drive, Winter Park 32789 Off market since Sep 2026 $4,595,000 · 5 bd · 6 ba · 5,211 sqft
- 1901 loch berry road, Winter Park 32792 Off market since Sep 2026 $3,500,000 · 5 bd · 6 ba · 4,831 sqft
- 857 brock street, Winter Park 32789 Off market since Sep 2026 $4,650,000 · 5 bd · 6 ba · 4,827 sqft
- 2407 lafayette avenue, Winter Park 32789 Off market since Sep 2026 $1,625,000 · 5 bd · 5 ba · 3,133 sqft
- 648 worthington drive, Winter Park 32789 Off market since Sep 2026 $2,700,000 · 5 bd · 5 ba · 3,588 sqft
- 120 longbranch road, Winter Park 32792 Off market since Sep 2026 $860,000 · 5 bd · 4 ba · 3,284 sqft
- 1526 miller avenue, Winter Park 32789 Off market since Sep 2026 $1,574,900 · 5 bd · 5 ba · 3,252 sqft
- 2181 linden road, Winter Park 32792 Off market since Sep 2026 $450,000 · 5 bd · 3 ba · 1,442 sqft
- 1761 legion drive, Winter Park 32789 Off market since Sep 2026 $3,265,000 · 5 bd · 6 ba · 4,949 sqft
- 724 monmouth way, Winter Park 32792 Off market since Sep 2026 $849,999 · 5 bd · 4 ba · 2,832 sqft
- 160 west rockwood way, Winter Park 32789 Off market since Sep 2026 $3,395,000 · 5 bd · 6 ba · 4,015 sqft
- 901 golfview terrace, Winter Park 32789 Off market since Sep 2026 $6,995,000 · 5 bd · 6 ba · 5,479 sqft
- 698 north new york avenue, Winter Park 32789 Off market since Sep 2026 $6,195,000 · 5 bd · 6 ba · 5,096 sqft
- 1773 walnut avenue, Winter Park 32789 Off market since Sep 2026 $2,725,000 · 5 bd · 5 ba · 3,784 sqft