Homes over $1M in Winter Park, FL
102 for sale · 206 homes listed · Updated November 9, 2026 · Page 2 of 5
- 1821 Englewood Road, Winter Park 32789 $2,950,000 · 5 bd · 6 ba · 3,863 sqft
- 1602 Alabama Drive #107, Winter Park 32789 $1,150,000 · 2 bd · 2 ba · 993 sqft
- 2228 Azalea Place, Winter Park 32789 $5,600,000 · 5 bd · 6 ba · 5,152 sqft
- 446 Melrose Avenue, Winter Park 32789 $1,495,000 · 4 bd · 2 ba · 2,640 sqft
- 698 North New York Avenue, Winter Park 32789 $5,995,000 · 5 bd · 6 ba · 5,096 sqft
- 532 Langholm Drive, Winter Park 32789 $2,990,000 · 5 bd · 5 ba · 4,050 sqft
- 2614 Parkland Drive, Winter Park 32789 $1,890,000 · 4 bd · 4 ba · 3,307 sqft
- 533 Country Club Drive, Winter Park 32789 $1,599,000 · 4 bd · 4 ba · 2,942 sqft
- 2430 Chantilly Avenue, Winter Park 32789 $1,550,000 · 4 bd · 4 ba · 2,916 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
- 914 Enclave Place, Winter Park 32792 $2,070,000 · 5 bd · 5 ba · 3,617 sqft
- 930 Enclave Place, Winter Park 32792 $2,275,000 · 5 bd · 5 ba · 3,813 sqft
- 938 Enclave Place, Winter Park 32792 $2,300,000 · 5 bd · 5 ba · 3,865 sqft
- 720 Pansy Avenue, Winter Park 32789 $1,295,000 · 3 bd · 4 ba · 2,191 sqft
- 641 Northwood Circle, Winter Park 32789 $1,499,000 · 3 bd · 5 ba · 2,756 sqft
- 240 North Phelps Avenue, Winter Park 32789 $1,999,900 · 5 bd · 5 ba · 2,889 sqft
- 1761 Legion Drive, Winter Park 32789 $3,265,000 · 5 bd · 6 ba · 4,949 sqft
- 555 East Lake Sue Avenue, Winter Park 32789 $2,000,000 · 4 bd · 4 ba · 3,776 sqft
- 2015 Summerfield Road, Winter Park 32792 $1,250,000 · 4 bd · 4 ba · 2,916 sqft
- 1951 Winter Park Road, Winter Park 32789 $1,949,000 · 4 bd · 4 ba · 3,479 sqft
- 100 South Virginia Avenue #201, Winter Park 32789 $1,450,000 · 3 bd · 3 ba · 2,756 sqft
- 1760 Oakhurst Avenue, Winter Park 32789 $2,500,000 · 5 bd · 5 ba · 3,700 sqft
- 513 Dunraven Drive, Winter Park 32792 $1,950,000 · 5 bd · 5 ba · 3,560 sqft
- 2007 Edwin Boulevard, Winter Park 32792 $1,995,000 · 4 bd · 4 ba · 3,314 sqft
- 2823 Parkland Circle, Winter Park 32789 $3,250,000 · 5 bd · 6 ba · 4,459 sqft
- 918 Enclave Place, Winter Park 32792 $2,125,000 · 5 bd · 5 ba · 3,713 sqft
- 2613 Lafayette Avenue, Winter Park 32789 $1,699,900 · 4 bd · 4 ba · 2,661 sqft
- 1737 Indiana Avenue, Winter Park 32789 $1,399,900 · 4 bd · 4 ba · 2,984 sqft
- 1751 Glencoe Road, Winter Park 32789 $3,390,000 · 5 bd · 7 ba · 4,520 sqft
- 1355 Hibiscus Avenue, Winter Park 32789 $2,100,000 · 5 bd · 6 ba · 4,155 sqft
- 1011 Mckean Circle, Winter Park 32789 $6,000,000 · 5 bd · 7 ba · 4,806 sqft
- 1445 Via Sangro Place, Winter Park 32792 $1,249,000 · 6 bd · 6 ba · 5,021 sqft
- 1939 Woodcrest Drive, Winter Park 32792 $1,349,000 · 4 bd · 4 ba · 2,575 sqft
- 1681 Woodland Avenue, Winter Park 32789 $2,629,000 · 5 bd · 5 ba · 3,682 sqft
- 1600 Legion Drive, Winter Park 32789 $3,495,000 · 5 bd · 6 ba · 4,483 sqft
- 617 North Interlachen Avenue, Winter Park 32789 $4,695,000 · 11 bd · 8 ba · 3,615 sqft
- 1825 Whitehall Drive, Winter Park 32789 $3,195,000 · 4 bd · 6 ba · 4,311 sqft
- 1631 Hillcrest Avenue, Winter Park 32789 $4,500,000 · 5 bd · 6 ba · 4,754 sqft
- 1735 Demetree Drive, Winter Park 32789 $1,050,000 · 4 bd · 3 ba · 2,787 sqft
- 1200 Via Salerno, Winter Park 32789 $5,995,000 · 5 bd · 6 ba · 5,476 sqft
- 1940 Magnolia Avenue, Winter Park 32792 $1,190,000 · 4 bd · 4 ba · 5,519 sqft
- 345 Beloit Avenue, Winter Park 32789 $1,625,000 · 3 bd · 3 ba · 2,884 sqft
- 541 Virginia Drive, Winter Park 32789 $5,695,000 · 4 bd · 4 ba · 4,725 sqft
- 1500 Harris Circle, Winter Park 32789 $1,175,000 · 3 bd · 3 ba · 2,096 sqft
- 1441 Palm Avenue, Winter Park 32789 $2,449,000 · 5 bd · 5 ba · 3,391 sqft
- 125 South Interlachen Avenue #4, Winter Park 32789 $3,995,000 · 3 bd · 5 ba · 3,885 sqft
- 2237 Woodcrest Drive, Winter Park 32792 $1,425,000 · 4 bd · 5 ba · 3,563 sqft
- 1534 Miller Avenue, Winter Park 32789 $1,379,900 · 4 bd · 4 ba · 2,984 sqft
- 1441 Grove Terrace, Winter Park 32789 $5,950,000 · 5 bd · 6 ba · 5,796 sqft