Homes over $1M in Winter Park, FL
127 for sale · 201 homes listed · Updated September 25, 2026 · Page 1 of 5
- 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
- 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
- 1840 anzle avenue, Winter Park 32789 $1,750,000 · 4 bd · 3 ba · 2,350 sqft
- 1751 goodrich avenue, Winter Park 32789 $1,380,000 · 4 bd · 4 ba · 2,170 sqft
- 1113 via del mar, Winter Park 32789 $1,595,000 · 3 bd · 2 ba · 2,012 sqft
- 1260 alabama drive, Winter Park 32789 $6,900,000 · 6 bd · 7 ba · 6,396 sqft
- 1581 forest avenue, Winter Park 32789 $3,275,000 · 4 bd · 6 ba · 4,683 sqft
- 1903 north park avenue, Winter Park 32789 $1,649,000 · 4 bd · 4 ba · 2,807 sqft
- 914 enclave place, Winter Park 32792 $2,070,000 · 5 bd · 5 ba · 3,617 sqft
- 905 enclave place, Winter Park 32792 $1,550,000 · 4 bd · 4 ba · 2,756 sqft
- 901 enclave place, Winter Park 32792 $1,550,000 · 4 bd · 4 ba · 2,738 sqft
- 1750 carollee lane, Winter Park 32789 $1,750,000 · 4 bd · 4 ba · 3,249 sqft
- 541 west canton avenue, Winter Park 32789 $2,495,000 · 4 bd · 4 ba · 3,553 sqft
- 1570 palmer avenue, Winter Park 32789 $1,595,000 · 4 bd · 4 ba · 3,048 sqft
- 621 huntington avenue, Winter Park 32789 $1,770,000 · 3 bd · 4 ba · 2,399 sqft
- 1870 staunton avenue, Winter Park 32789 $1,250,000 · 4 bd · 4 ba · 2,525 sqft
- 1881 lake spier drive, Winter Park 32789 $1,350,000 · 3 bd · 2 ba · 1,750 sqft
- 2702 parkland drive, Winter Park 32789 $1,049,000 · 5 bd · 3 ba · 2,656 sqft
- 102 bell place, Winter Park 32792 $1,299,000 · 4 bd · 4 ba · 2,459 sqft
- 1441 cardinal court, Winter Park 32789 $3,995,000 · 4 bd · 6 ba · 4,066 sqft
- 446 melrose avenue, Winter Park 32789 $1,595,000 · 4 bd · 2 ba · 2,640 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
- 1600 south pennsylvania avenue, Winter Park 32789 $1,150,000 · 3 bd · 2 ba · 2,158 sqft
- 1606 miller avenue, Winter Park 32789 $1,249,900 · 4 bd · 4 ba · 2,936 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
- 1841 lake spier drive, Winter Park 32789 $1,498,000 · 3 bd · 4 ba · 2,467 sqft
- 125 south interlachen avenue 2, Winter Park 32789 $3,150,000 · 3 bd · 5 ba · 3,244 sqft
- 1448 lake florence way, Winter Park 32792 $1,049,900 · 5 bd · 5 ba · 3,652 sqft
- 723 symonds avenue, Winter Park 32789 $1,700,000 · 4 bd · 4 ba · 3,065 sqft
- 946 enclave place, Winter Park 32792 $2,375,000 · 5 bd · 5 ba · 3,989 sqft
- 1581 magnolia avenue, Winter Park 32789 $1,425,000 · 4 bd · 4 ba · 2,756 sqft
- 1571 woodland avenue, Winter Park 32789 $6,000,000 · 5 bd · 8 ba · 7,397 sqft
- 1404 border drive, Winter Park 32789 $1,075,000 · 4 bd · 4 ba · 2,469 sqft
- 641 northwood circle, Winter Park 32789 $1,540,000 · 3 bd · 5 ba · 2,756 sqft
- 2240 venetian way, Winter Park 32789 $3,500,000 · 4 bd · 4 ba · 4,036 sqft
- 413 west morse boulevard, Winter Park 32789 $2,625,000 · 3 bd · 4 ba · 3,048 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
- 231 chelton circle, Winter Park 32789 $4,950,000 · 4 bd · 7 ba · 5,550 sqft
- 240 north phelps avenue, Winter Park 32789 $2,050,000 · 5 bd · 5 ba · 2,889 sqft
- 1421 chapman circle, Winter Park 32789 $1,377,500 · 4 bd · 4 ba · 3,578 sqft
- 1836 whitehall drive, Winter Park 32789 $2,995,000 · 5 bd · 7 ba · 4,168 sqft
- 313 sylvan drive, Winter Park 32789 $5,500,000 · 4 bd · 5 ba · 4,775 sqft
- 101 south new york avenue 311, Winter Park 32789 $1,775,000 · 3 bd · 4 ba · 3,112 sqft