5 Bedroom Homes in Winter Park, FL
48 for sale · 75 homes listed · Updated September 27, 2026 · Page 1 of 2
- 1821 englewood road, Winter Park 32789 $3,075,000 · 5 bd · 6 ba · 3,863 sqft
- 207 east kings way, Winter Park 32789 $3,600,000 · 5 bd · 5 ba · 3,719 sqft
- 2612 roxbury road, Winter Park 32789 $629,900 · 5 bd · 3 ba · 2,472 sqft
- 1885 temple drive, Winter Park 32789 $2,195,000 · 5 bd · 4 ba · 3,691 sqft
- 1523 miller avenue, Winter Park 32789 $1,399,000 · 5 bd · 4 ba · 3,164 sqft
- 1927 eland avenue, Winter Park 32789 $820,000 · 5 bd · 3 ba · 2,242 sqft
- 914 enclave place, Winter Park 32792 $2,070,000 · 5 bd · 5 ba · 3,617 sqft
- 2702 parkland drive, Winter Park 32789 $1,049,000 · 5 bd · 3 ba · 2,656 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 $2,275,000 · 5 bd · 5 ba · 3,813 sqft
- 1627 mizell avenue, Winter Park 32789 $3,300,000 · 5 bd · 6 ba · 3,421 sqft
- 938 enclave place, Winter Park 32792 $2,300,000 · 5 bd · 5 ba · 3,865 sqft
- 926 enclave place, Winter Park 32792 $2,475,000 · 5 bd · 5 ba · 4,150 sqft
- 1448 lake florence way, Winter Park 32792 $1,049,900 · 5 bd · 5 ba · 3,652 sqft
- 946 enclave place, Winter Park 32792 $2,375,000 · 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 $1,369,000 · 5 bd · 4 ba · 2,351 sqft
- 240 north phelps avenue, Winter Park 32789 $2,050,000 · 5 bd · 5 ba · 2,889 sqft
- 1836 whitehall drive, Winter Park 32789 $2,995,000 · 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
- 1754 taylor avenue, Winter Park 32789 $2,569,999 · 5 bd · 5 ba · 3,670 sqft
- 777 halifax avenue, Winter Park 32792 $1,449,000 · 5 bd · 5 ba · 3,109 sqft
- 724 monmouth way, Winter Park 32792 $798,000 · 5 bd · 4 ba · 2,832 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 $4,595,000 · 5 bd · 6 ba · 5,211 sqft
- 857 brock street, Winter Park 32789 $4,650,000 · 5 bd · 6 ba · 4,827 sqft
- 2407 lafayette avenue, Winter Park 32789 $1,625,000 · 5 bd · 5 ba · 3,133 sqft
- 648 worthington drive, Winter Park 32789 $2,700,000 · 5 bd · 5 ba · 3,588 sqft
- 120 longbranch road, Winter Park 32792 $860,000 · 5 bd · 4 ba · 3,284 sqft
- 1526 miller avenue, Winter Park 32789 $1,574,900 · 5 bd · 5 ba · 3,252 sqft
- 2181 linden road, Winter Park 32792 $450,000 · 5 bd · 3 ba · 1,442 sqft
- 1761 legion drive, Winter Park 32789 $3,265,000 · 5 bd · 6 ba · 4,924 sqft
- 1164 dodd road, Winter Park 32792 $795,000 · 5 bd · 4 ba · 2,840 sqft
- 160 west rockwood way, Winter Park 32789 $3,395,000 · 5 bd · 6 ba · 4,015 sqft
- 901 golfview terrace, Winter Park 32789 $6,995,000 · 5 bd · 6 ba · 5,479 sqft
- 698 north new york avenue, Winter Park 32789 $6,195,000 · 5 bd · 6 ba · 5,096 sqft
- 1773 walnut avenue, Winter Park 32789 $2,725,000 · 5 bd · 5 ba · 3,784 sqft
- 825 palmer avenue, Winter Park 32789 $5,195,900 · 5 bd · 7 ba · 5,122 sqft
- 2260 mulbry drive, Winter Park 32789 $1,925,000 · 5 bd · 4 ba · 3,246 sqft
- 250 west reading way, Winter Park 32789 $4,325,000 · 5 bd · 5 ba · 4,853 sqft
- 1166 palmer avenue, Winter Park 32789 $5,500,000 · 5 bd · 7 ba · 5,181 sqft
- 662 granville drive, Winter Park 32789 $3,495,000 · 5 bd · 6 ba · 4,478 sqft
- 532 langholm drive, Winter Park 32789 $2,990,000 · 5 bd · 5 ba · 4,050 sqft
- 1510 miller avenue, Winter Park 32789 Pending $1,599,900 · 5 bd · 5 ba · 3,252 sqft
- 550 palmer avenue, Winter Park 32789 Pending $6,495,000 · 5 bd · 7 ba · 5,939 sqft