Homes over $1M in Winter Park, FL
102 for sale · 206 homes listed · Updated November 9, 2026 · Page 1 of 5
- 1591 Cardinal Court, Winter Park 32789 $2,995,000 · 5 bd · 3 ba · 3,523 sqft
- 231 Chelton Circle, Winter Park 32789 $4,500,000 · 4 bd · 7 ba · 5,550 sqft
- 230 Killarney Drive, Winter Park 32789 $1,150,000 · 4 bd · 1 ba · 1,260 sqft
- 240 Killarney Drive, Winter Park 32789 $1,175,000 · 3 bd · 3 ba · 1,329 sqft
- 1113 Via Del Mar, Winter Park 32789 $1,595,000 · 3 bd · 2 ba · 2,012 sqft
- 1546 Miller Avenue, Winter Park 32789 $1,429,900 · 4 bd · 4 ba · 2,984 sqft
- 125 South Interlachen Avenue #2, Winter Park 32789 $2,995,000 · 3 bd · 5 ba · 3,244 sqft
- 1840 Anzle Avenue, Winter Park 32789 $1,750,000 · 4 bd · 3 ba · 2,350 sqft
- 281 Brewer Avenue, Winter Park 32789 $1,800,000 · 5 bd · 5 ba · 4,029 sqft
- 2308 Mulbry Drive, Winter Park 32789 $1,699,000 · 4 bd · 4 ba · 2,530 sqft
- 276 Detmar Drive, Winter Park 32789 $3,600,000 · 4 bd · 5 ba · 4,202 sqft
- 413 West Morse Boulevard, Winter Park 32789 $2,625,000 · 3 bd · 4 ba · 3,048 sqft
- 1441 Cardinal Court, Winter Park 32789 $3,600,000 · 4 bd · 6 ba · 4,066 sqft
- 150 East Reading Way, Winter Park 32789 $1,349,000 · 3 bd · 3 ba · 2,080 sqft
- 1840 Bryan Avenue, Winter Park 32789 $1,725,000 · 4 bd · 4 ba · 3,727 sqft
- 200 South Interlachen Avenue #350, Winter Park 32789 $2,350,000 · 3 bd · 4 ba · 3,110 sqft
- 2661 Via Tuscany, Winter Park 32789 $5,500,000 · 4 bd · 5 ba · 3,880 sqft
- 2622 Lake Howell Lane, Winter Park 32792 $3,750,000 · 4 bd · 3 ba · 3,377 sqft
- 660 West Morse Boulevard, Winter Park 32789 $2,695,000 · 3 bd · 4 ba · 3,286 sqft
- 702 Via Bella, Winter Park 32789 $4,090,000 · 4 bd · 6 ba · 3,720 sqft
- 540 North Pennsylvania Avenue, Winter Park 32789 $3,950,000 · 4 bd · 2 ba · 1,652 sqft
- 450 Lakewood Drive, Winter Park 32789 $2,500,000 · 5 bd · 6 ba · 4,572 sqft
- 922 North Pennsylvania Avenue, Winter Park 32789 $1,795,000 · 4 bd · 4 ba · 3,440 sqft
- 462 West Lyman Avenue, Winter Park 32789 $1,450,000 · 3 bd · 3 ba · 1,944 sqft
- 825 Palmer Avenue, Winter Park 32789 $5,195,900 · 5 bd · 7 ba · 5,122 sqft
- 2119 Howard Drive, Winter Park 32789 $3,195,000 · 5 bd · 6 ba · 4,139 sqft
- 512 West Swoope Avenue, Winter Park 32789 $1,399,000 · 3 bd · 3 ba · 2,585 sqft
- 504 West Swoope Avenue, Winter Park 32789 $1,300,000 · 3 bd · 3 ba · 2,563 sqft
- 901 Golfview Terrace, Winter Park 32789 $6,795,000 · 5 bd · 6 ba · 5,479 sqft
- 1166 Palmer Avenue, Winter Park 32789 $5,500,000 · 5 bd · 7 ba · 5,181 sqft
- 1803 Barker Drive, Winter Park 32789 $2,190,000 · 4 bd · 3 ba · 3,463 sqft
- 2207 Kindel Avenue, Winter Park 32789 $1,575,000 · 3 bd · 3 ba · 2,733 sqft
- 1517 Harmon Avenue, Winter Park 32789 $1,049,000 · 4 bd · 4 ba · 2,135 sqft
- 1473 Berkshire Avenue, Winter Park 32789 $1,369,000 · 5 bd · 4 ba · 2,446 sqft
- 1260 Alabama Drive, Winter Park 32789 $6,900,000 · 6 bd · 7 ba · 6,396 sqft
- 102 Bell Place, Winter Park 32792 $1,299,000 · 4 bd · 4 ba · 2,459 sqft
- 1742 Temple Drive, Winter Park 32789 $3,545,995 · 4 bd · 5 ba · 3,658 sqft
- 1133 Bella Lago Cove, Winter Park 32792 $1,999,900 · 3 bd · 2 ba · 1,765 sqft
- 2343 Versailles Avenue, Winter Park 32789 $1,675,000 · 4 bd · 4 ba · 3,307 sqft
- 662 Granville Drive, Winter Park 32789 $3,495,000 · 5 bd · 6 ba · 4,478 sqft
- 857 Brock Street, Winter Park 32789 $4,350,000 · 5 bd · 6 ba · 4,827 sqft
- 620 Virginia Drive, Winter Park 32789 $3,890,000 · 6 bd · 5 ba · 4,677 sqft
- 1773 Walnut Avenue, Winter Park 32789 $2,725,000 · 5 bd · 5 ba · 3,784 sqft
- 125 South Interlachen Avenue #1, Winter Park 32789 $3,645,000 · 3 bd · 5 ba · 3,878 sqft
- 1271 Palmer Avenue, Winter Park 32789 $2,125,000 · 4 bd · 5 ba · 2,850 sqft
- 751 Pansy Avenue, Winter Park 32789 $1,875,000 · 3 bd · 4 ba · 2,703 sqft
- 1922 Hammerlin Avenue, Winter Park 32789 $1,095,000 · 3 bd · 3 ba · 1,873 sqft
- 120 Broadview Avenue, Winter Park 32789 $1,250,000 · 3 bd · 2 ba · 1,747 sqft
- 1570 Palmer Avenue, Winter Park 32789 $1,485,000 · 4 bd · 4 ba · 3,048 sqft
- 101 South New York Avenue #311, Winter Park 32789 $1,775,000 · 3 bd · 4 ba · 3,112 sqft