Homes over $1M in Winter Park, FL
105 homes for sale · Updated August 12, 2026 · Page 2 of 3
- 946 enclave place, Winter Park 32792 $2,175,000 · 5 bd · 5 ba · 3,989 sqft
- 1581 magnolia avenue, Winter Park 32789 $1,465,000 · 4 bd · 4 ba · 2,756 sqft
- 1571 woodland avenue, Winter Park 32789 $6,000,000 · 5 bd · 8 ba · 7,397 sqft
- 1404 border drive, Winter Park 32789 $1,100,000 · 4 bd · 4 ba · 2,469 sqft
- 641 northwood circle, Winter Park 32789 $1,599,000 · 3 bd · 5 ba · 2,756 sqft
- 649 north park avenue, Winter Park 32789 $3,500,000 · 3 bd · 5 ba · 3,180 sqft
- 2240 venetian way, Winter Park 32789 $3,500,000 · 4 bd · 4 ba · 4,036 sqft
- 413 west morse boulevard, Winter Park 32789 $2,695,000 · 3 bd · 4 ba · 3,048 sqft
- 2032 kimbrace place, Winter Park 32792 $1,800,000 · 5 bd · 4 ba · 3,382 sqft
- 1473 berkshire avenue, Winter Park 32789 $1,429,000 · 5 bd · 4 ba · 2,351 sqft
- 231 chelton circle, Winter Park 32789 $4,950,000 · 4 bd · 7 ba · 5,550 sqft
- 240 north phelps avenue, Winter Park 32789 $2,150,000 · 5 bd · 5 ba · 2,889 sqft
- 1421 chapman circle, Winter Park 32789 $1,450,000 · 4 bd · 4 ba · 3,578 sqft
- 1836 whitehall drive, Winter Park 32789 $3,500,000 · 5 bd · 7 ba · 4,168 sqft
- 313 sylvan drive, Winter Park 32789 $5,500,000 · 4 bd · 5 ba · 4,775 sqft
- 140 east morse boulevard j, Winter Park 32789 $2,350,000 · 3 bd · 3 ba · 2,143 sqft
- 101 south new york avenue 311, Winter Park 32789 $1,849,900 · 3 bd · 4 ba · 3,112 sqft
- 512 west swoope avenue, Winter Park 32789 $1,399,000 · 3 bd · 3 ba · 2,585 sqft
- 2015 summerfield road, Winter Park 32792 $1,262,500 · 4 bd · 4 ba · 3,024 sqft
- 2914 reef knot place, Winter Park 32792 $1,725,000 · 6 bd · 6 ba · 4,173 sqft
- 1591 cardinal court, Winter Park 32789 $2,995,000 · 5 bd · 3 ba · 3,523 sqft
- 660 west morse boulevard, Winter Park 32789 $2,800,000 · 3 bd · 4 ba · 3,286 sqft
- 3006 northwood boulevard, Winter Park 32789 $1,099,000 · 4 bd · 3 ba · 2,075 sqft
- 1138 south pennsylvania avenue, Winter Park 32789 $1,025,000 · 3 bd · 3 ba · 2,434 sqft
- 2228 azalea place, Winter Park 32789 $5,600,000 · 5 bd · 6 ba · 5,152 sqft
- 341 east reading way, Winter Park 32789 $1,625,000 · 4 bd · 4 ba · 3,723 sqft
- 1823 sunset drive, Winter Park 32789 $2,549,000 · 5 bd · 5 ba · 3,479 sqft
- 1180 via lugano, Winter Park 32789 $4,900,000 · 5 bd · 6 ba · 4,961 sqft
- 1754 taylor avenue, Winter Park 32789 $2,569,999 · 5 bd · 5 ba · 3,670 sqft
- 708 balmoral road, Winter Park 32789 $1,690,000 · 4 bd · 3 ba · 2,786 sqft
- 777 halifax avenue, Winter Park 32792 $1,500,000 · 5 bd · 5 ba · 3,109 sqft
- 229 alexander place, Winter Park 32789 $4,250,000 · 4 bd · 6 ba · 4,431 sqft
- 462 west lyman avenue, Winter Park 32789 $1,595,000 · 3 bd · 3 ba · 1,944 sqft
- 922 north pennsylvania avenue, Winter Park 32789 $1,995,000 · 4 bd · 4 ba · 3,440 sqft
- 250 killarney, Winter Park 32789 $1,600,000 · 4 bd · 4 ba · 2,568 sqft
- 1133 bella lago cove, Winter Park 32792 $2,100,000 · 3 bd · 2 ba · 1,765 sqft
- 230 killarney drive, Winter Park 32789 $1,250,000 · 4 bd · 1 ba · 1,260 sqft
- 240 killarney drive, Winter Park 32789 $1,275,000 · 3 bd · 3 ba · 1,329 sqft
- 281 brewer avenue, Winter Park 32789 $1,800,000 · 5 bd · 5 ba · 4,029 sqft
- 1271 palmer avenue, Winter Park 32789 $2,275,000 · 4 bd · 5 ba · 2,835 sqft
- 2661 via tuscany, Winter Park 32789 $6,888,888 · 4 bd · 5 ba · 4,636 sqft
- 1546 miller avenue, Winter Park 32789 $1,419,900 · 4 bd · 4 ba · 2,984 sqft
- 2525 lafayette avenue, Winter Park 32789 $1,749,000 · 4 bd · 4 ba · 2,715 sqft
- 1840 laurel road, Winter Park 32789 $2,299,000 · 5 bd · 5 ba · 2,868 sqft
- 125 south interlachen avenue 1, Winter Park 32789 $3,895,000 · 3 bd · 5 ba · 3,878 sqft
- 525 south lakemont avenue, Winter Park 32792 $2,099,990 · 4 bd · 4 ba · 3,330 sqft
- 1525 granville drive, Winter Park 32789 $4,750,000 · 5 bd · 6 ba · 5,211 sqft
- 645 pansy avenue, Winter Park 32789 $2,390,000 · 4 bd · 5 ba · 3,661 sqft
- 361 east kings way, Winter Park 32789 $3,199,000 · 4 bd · 5 ba · 3,737 sqft
- 2667 cochise trail, Winter Park 32789 $1,000,050 · 4 bd · 3 ba · 2,868 sqft