Homes over $1M in Winter Park, FL

105 homes for sale · Updated August 12, 2026 · Page 1 of 3

• 1150 via salerno, Winter Park 32789 $3,975,000 · 4 bd · 6 ba · 3,850 sqft
• 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
• 607 ellen drive, Winter Park 32789 $1,389,500 · 4 bd · 5 ba · 2,812 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
• 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
• 40 palmer avenue, Winter Park 32789 $7,250,000 · 5 bd · 6 ba · 5,905 sqft
• 1260 alabama drive, Winter Park 32789 $6,900,000 · 6 bd · 7 ba · 6,396 sqft
• 2501 winter park road, Winter Park 32789 $1,649,000 · 5 bd · 4 ba · 3,304 sqft
• 1581 forest avenue, Winter Park 32789 $3,275,000 · 4 bd · 6 ba · 4,683 sqft
• 1870 walker avenue, Winter Park 32789 $1,199,000 · 3 bd · 3 ba · 2,046 sqft
• 1903 north park avenue, Winter Park 32789 $1,695,000 · 4 bd · 4 ba · 2,807 sqft
• 914 enclave place, Winter Park 32792 $1,895,000 · 5 bd · 5 ba · 3,617 sqft
• 905 enclave place, Winter Park 32792 $1,495,000 · 4 bd · 4 ba · 2,756 sqft
• 901 enclave place, Winter Park 32792 $1,495,000 · 4 bd · 4 ba · 2,738 sqft
• 1750 carollee lane, Winter Park 32789 $1,780,000 · 4 bd · 4 ba · 3,249 sqft
• 541 west canton avenue, Winter Park 32789 $2,650,000 · 4 bd · 4 ba · 3,553 sqft
• 621 huntington avenue, Winter Park 32789 $1,795,000 · 3 bd · 4 ba · 2,399 sqft
• 1870 staunton avenue, Winter Park 32789 $1,250,000 · 4 bd · 4 ba · 2,525 sqft
• 2702 parkland drive, Winter Park 32789 $1,049,000 · 5 bd · 3 ba · 2,656 sqft
• 102 bell place, Winter Park 32792 $1,349,000 · 4 bd · 4 ba · 2,459 sqft
• 1441 cardinal court, Winter Park 32789 $4,285,000 · 4 bd · 6 ba · 4,066 sqft
• 1398 grove terrace, Winter Park 32789 $1,995,000 · 4 bd · 4 ba · 3,450 sqft
• 802 hamilton place court, Winter Park 32789 $1,295,000 · 4 bd · 4 ba · 2,843 sqft
• 2838 wright avenue, Winter Park 32789 $2,399,000 · 5 bd · 5 ba · 3,479 sqft
• 446 melrose avenue, Winter Park 32789 $1,625,000 · 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
• 311 east morse boulevard 1-3, Winter Park 32789 $1,825,000 · 2 bd · 2 ba · 2,304 sqft
• 1606 miller avenue, Winter Park 32789 $1,249,900 · 4 bd · 4 ba · 2,936 sqft
• 2228 howard drive, Winter Park 32789 $2,460,000 · 4 bd · 4 ba · 3,294 sqft
• 2430 chantilly avenue, Winter Park 32789 $1,599,000 · 4 bd · 4 ba · 2,916 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
• 622 penn place, Winter Park 32789 $1,895,000 · 3 bd · 4 ba · 2,767 sqft
• 120 broadview avenue, Winter Park 32789 $1,450,000 · 3 bd · 2 ba · 1,747 sqft
• 1120 wisconsin avenue, Winter Park 32789 $1,084,000 · 3 bd · 4 ba · 2,213 sqft
• 1841 lake spier drive, Winter Park 32789 $1,595,000 · 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 $1,099,900 · 5 bd · 5 ba · 3,652 sqft
• 723 symonds avenue, Winter Park 32789 $1,800,000 · 4 bd · 4 ba · 3,065 sqft
• 1420 magnolia avenue, Winter Park 32789 $1,695,000 · 4 bd · 4 ba · 3,174 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