Homes over $1M in Winter Park, FL

81 for sale · 280 homes listed · Updated September 27, 2026 · Page 4 of 6

• 318 vitoria avenue, Winter Park 32789 Off market since Jul 2026 $1,980,000 · 3 bd · 3 ba · 2,433 sqft
• 621 huntington avenue, Winter Park 32789 Off market since Sep 2026 $1,770,000 · 3 bd · 4 ba · 2,399 sqft
• 1870 staunton avenue, Winter Park 32789 Off market since Sep 2026 $1,250,000 · 4 bd · 4 ba · 2,525 sqft
• 1881 lake spier drive, Winter Park 32789 Off market since Sep 2026 $1,350,000 · 3 bd · 2 ba · 1,750 sqft
• 2702 parkland drive, Winter Park 32789 Off market since Sep 2026 $1,049,000 · 5 bd · 3 ba · 2,656 sqft
• 1540 miller avenue, Winter Park 32789 Off market since Jul 2026 $1,399,900 · 4 bd · 4 ba · 2,984 sqft
• 102 bell place, Winter Park 32792 Off market since Sep 2026 $1,299,000 · 4 bd · 4 ba · 2,459 sqft
• 1441 cardinal court, Winter Park 32789 Off market since Sep 2026 $3,995,000 · 4 bd · 6 ba · 4,066 sqft
• 1398 grove terrace, Winter Park 32789 Off market since Sep 2026 $1,995,000 · 4 bd · 4 ba · 3,450 sqft
• 2838 wright avenue, Winter Park 32789 Off market since Sep 2026 $2,399,000 · 5 bd · 5 ba · 3,479 sqft
• 2111 mallard circle, Winter Park 32789 Off market since Jul 2026 $1,199,000 · 4 bd · 3 ba · 2,667 sqft
• 363 north phelps avenue, Winter Park 32789 Off market since Jul 2026 $1,249,000 · 4 bd · 3 ba · 2,871 sqft
• 420 ohio street, Winter Park 32789 Off market since Jul 2026 $1,275,000 · 4 bd · 4 ba · 2,900 sqft
• 446 melrose avenue, Winter Park 32789 Off market since Sep 2026 $1,525,000 · 4 bd · 2 ba · 2,640 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
• 2232 banchory road, Winter Park 32792 Off market since Jul 2026 $1,115,000 · 4 bd · 3 ba · 2,597 sqft
• 141 west lake sue avenue, Winter Park 32789 Off market since Jul 2026 $4,200,000 · 5 bd · 7 ba · 5,500 sqft
• 1600 south pennsylvania avenue, Winter Park 32789 Off market since Sep 2026 $1,150,000 · 3 bd · 2 ba · 2,158 sqft
• 1606 miller avenue, Winter Park 32789 Off market since Sep 2026 $1,249,900 · 4 bd · 4 ba · 2,936 sqft
• 2430 chantilly avenue, Winter Park 32789 Off market since Sep 2026 $1,599,000 · 4 bd · 4 ba · 2,916 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
• 622 penn place, Winter Park 32789 Off market since Sep 2026 $1,895,000 · 3 bd · 4 ba · 2,767 sqft
• 1841 lake spier drive, Winter Park 32789 Off market since Sep 2026 $1,498,000 · 3 bd · 4 ba · 2,467 sqft
• 125 south interlachen avenue 2, Winter Park 32789 Off market since Sep 2026 $3,150,000 · 3 bd · 5 ba · 3,244 sqft
• 1448 lake florence way, Winter Park 32792 Off market since Sep 2026 $1,049,900 · 5 bd · 5 ba · 3,652 sqft
• 723 symonds avenue, Winter Park 32789 Off market since Sep 2026 $1,700,000 · 4 bd · 4 ba · 3,065 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
• 1581 magnolia avenue, Winter Park 32789 Off market since Sep 2026 $1,425,000 · 4 bd · 4 ba · 2,756 sqft
• 1571 woodland avenue, Winter Park 32789 Off market since Sep 2026 $6,000,000 · 5 bd · 8 ba · 7,397 sqft
• 1404 border drive, Winter Park 32789 Off market since Sep 2026 $1,075,000 · 4 bd · 4 ba · 2,469 sqft
• 641 northwood circle, Winter Park 32789 Off market since Sep 2026 $1,499,000 · 3 bd · 5 ba · 2,756 sqft
• 649 north park avenue, Winter Park 32789 Off market since Sep 2026 $3,500,000 · 3 bd · 5 ba · 3,180 sqft
• 2240 venetian way, Winter Park 32789 Off market since Sep 2026 $3,500,000 · 4 bd · 4 ba · 4,036 sqft
• 413 west morse boulevard, Winter Park 32789 Off market since Sep 2026 $2,625,000 · 3 bd · 4 ba · 3,048 sqft
• 525 south lakemont avenue, Winter Park 32792 Off market since Aug 2026 $2,099,990 · 4 bd · 4 ba · 3,330 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
• 231 chelton circle, Winter Park 32789 Off market since Sep 2026 $4,950,000 · 4 bd · 7 ba · 5,550 sqft
• 240 north phelps avenue, Winter Park 32789 Off market since Sep 2026 $2,050,000 · 5 bd · 5 ba · 2,889 sqft
• 1421 chapman circle, Winter Park 32789 Off market since Sep 2026 $1,377,500 · 4 bd · 4 ba · 3,578 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