Homes over $1M in Winter Park, FL

81 for sale · 280 homes listed · Updated September 27, 2026 · Page 3 of 6

• 1649 harmon avenue, Winter Park 32789 Active Under Contract $1,250,000 · 4 bd · 4 ba · 3,223 sqft
• 1130 park north place, Winter Park 32789 Active Under Contract $2,200,000 · 5 bd · 4 ba · 4,011 sqft
• 802 hamilton place court, Winter Park 32789 Active Under Contract $1,295,000 · 4 bd · 4 ba · 2,843 sqft
• 106 south interlachen avenue 518, Winter Park 32789 Active Under Contract $1,795,000 · 3 bd · 2 ba · 1,807 sqft
• 1981 blue ridge road, Winter Park 32789 Active Under Contract $1,150,000 · 4 bd · 2 ba · 2,750 sqft
• 1813 harland park drive, Winter Park 32789 Active Under Contract $1,875,000 · 4 bd · 4 ba · 3,551 sqft
• 311 east morse boulevard 1-3, Winter Park 32789 Active Under Contract $1,825,000 · 2 bd · 2 ba · 2,304 sqft
• 1420 magnolia avenue, Winter Park 32789 Active Under Contract $1,690,000 · 4 bd · 4 ba · 3,174 sqft
• 1600 alabama drive 402, Winter Park 32789 Active Under Contract $1,250,000 · 2 bd · 2 ba · 1,574 sqft
• 426 worthington drive, Winter Park 32789 Active Under Contract $2,499,000 · 5 bd · 5 ba · 3,520 sqft
• 1750 walnut avenue, Winter Park 32789 Active Under Contract $2,195,000 · 4 bd · 5 ba · 3,691 sqft
• 229 alexander place, Winter Park 32789 Active Under Contract $4,250,000 · 4 bd · 6 ba · 4,431 sqft
• 1351 oneco avenue, Winter Park 32789 Active Under Contract $1,150,000 · 4 bd · 3 ba · 2,474 sqft
• 570 manor road maitland, Winter Park 32751 Active Under Contract $12,500,000 · 6 bd · 10 ba · 10,172 sqft
• 2525 temple drive, Winter Park 32789 Active Under Contract $4,750,000 · 5 bd · 5 ba · 4,542 sqft
• 2138 talman court, Winter Park 32792 Active Under Contract $1,450,000 · 4 bd · 5 ba · 4,249 sqft
• 645 pansy avenue, Winter Park 32789 Active Under Contract $2,390,000 · 4 bd · 5 ba · 3,661 sqft
• 890 north phelps avenue, Winter Park 32789 Active Under Contract $1,775,000 · 4 bd · 5 ba · 3,630 sqft
• 948 poinciana lane, Winter Park 32789 Active Under Contract $2,750,000 · 4 bd · 5 ba · 3,676 sqft
• 1417 williams drive, Winter Park 32789 Active Under Contract $3,999,000 · 5 bd · 6 ba · 4,891 sqft
• 1661 laurel road, Winter Park 32789 Active Under Contract $1,875,000 · 3 bd · 3 ba · 3,127 sqft
• 1230 sunset drive, Winter Park 32789 Active Under Contract $1,795,000 · 4 bd · 4 ba · 3,250 sqft
• 631 williams drive, Winter Park 32789 Active Under Contract $1,824,000 · 4 bd · 4 ba · 2,972 sqft
• 2873 old castle drive, Winter Park 32792 Active Under Contract $1,395,000 · 4 bd · 4 ba · 4,247 sqft
• 2614 parkland drive, Winter Park 32789 Off market since Jul 2026 $1,894,000 · 4 bd · 4 ba · 3,307 sqft
• 1821 englewood road, Winter Park 32789 Off market since Sep 2026 $3,075,000 · 5 bd · 6 ba · 3,863 sqft
• 207 east kings way, Winter Park 32789 Off market since Sep 2026 $3,600,000 · 5 bd · 5 ba · 3,719 sqft
• 1751 glencoe road, Winter Park 32789 Off market since Aug 2026 $3,390,000 · 5 bd · 7 ba · 4,520 sqft
• 1885 temple drive, Winter Park 32789 Off market since Sep 2026 $2,195,000 · 5 bd · 4 ba · 3,691 sqft
• 1523 miller avenue, Winter Park 32789 Off market since Sep 2026 $1,399,000 · 5 bd · 4 ba · 3,164 sqft
• 948 poinciana lane, Winter Park 32789 Off market since Jul 2026 $2,899,900 · 4 bd · 4 ba · 3,676 sqft
• 1840 anzle avenue, Winter Park 32789 Off market since Sep 2026 $1,750,000 · 4 bd · 3 ba · 2,350 sqft
• 1751 goodrich avenue, Winter Park 32789 Off market since Sep 2026 $1,380,000 · 4 bd · 4 ba · 2,170 sqft
• 147 south interlachen avenue 202, Winter Park 32789 Off market since Aug 2026 $2,100,000 · 3 bd · 5 ba · 3,272 sqft
• 1113 via del mar, Winter Park 32789 Off market since Sep 2026 $1,595,000 · 3 bd · 2 ba · 2,012 sqft
• 40 palmer avenue, Winter Park 32789 Off market since Sep 2026 $7,250,000 · 5 bd · 6 ba · 5,905 sqft
• 1500 harris circle, Winter Park 32789 Off market since Jul 2026 $1,195,000 · 2 bd · 3 ba · 2,096 sqft
• 1200 via salerno, Winter Park 32789 Off market since Jul 2026 $5,995,000 · 5 bd · 6 ba · 5,476 sqft
• 100 south interlachen avenue 101, Winter Park 32789 Off market since Jul 2026 $1,299,000 · 3 bd · 2 ba · 1,734 sqft
• 1260 alabama drive, Winter Park 32789 Off market since Sep 2026 $6,900,000 · 6 bd · 7 ba · 6,396 sqft
• 1581 forest avenue, Winter Park 32789 Off market since Sep 2026 $3,275,000 · 4 bd · 6 ba · 4,683 sqft
• 609 south phelps avenue, Winter Park 32789 Off market since Jul 2026 $2,829,000 · 5 bd · 5 ba · 4,018 sqft
• 1903 north park avenue, Winter Park 32789 Off market since Sep 2026 $1,649,000 · 4 bd · 4 ba · 2,807 sqft
• 914 enclave place, Winter Park 32792 Off market since Sep 2026 $2,070,000 · 5 bd · 5 ba · 3,617 sqft
• 905 enclave place, Winter Park 32792 Off market since Sep 2026 $1,550,000 · 4 bd · 4 ba · 2,756 sqft
• 901 enclave place, Winter Park 32792 Off market since Sep 2026 $1,550,000 · 4 bd · 4 ba · 2,738 sqft
• 1750 carollee lane, Winter Park 32789 Off market since Sep 2026 $1,750,000 · 4 bd · 4 ba · 3,249 sqft
• 1840 bryan avenue, Winter Park 32789 Off market since Aug 2026 $1,725,000 · 4 bd · 4 ba · 3,727 sqft
• 541 west canton avenue, Winter Park 32789 Off market since Sep 2026 $2,495,000 · 4 bd · 4 ba · 3,553 sqft
• 1570 palmer avenue, Winter Park 32789 Off market since Sep 2026 $1,595,000 · 4 bd · 4 ba · 3,048 sqft