Homes over $1M in Winter Park, FL

127 for sale · 201 homes listed · Updated September 25, 2026 · Page 2 of 5

• 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
• 2228 azalea place, Winter Park 32789 $5,600,000 · 5 bd · 6 ba · 5,152 sqft
• 341 east reading way, Winter Park 32789 $1,525,000 · 4 bd · 4 ba · 3,723 sqft
• 1823 sunset drive, Winter Park 32789 $2,549,000 · 5 bd · 5 ba · 3,479 sqft
• 1754 taylor avenue, Winter Park 32789 $2,569,999 · 5 bd · 5 ba · 3,670 sqft
• 777 halifax avenue, Winter Park 32792 $1,449,000 · 5 bd · 5 ba · 3,109 sqft
• 462 west lyman avenue, Winter Park 32789 $1,495,000 · 3 bd · 3 ba · 1,944 sqft
• 922 north pennsylvania avenue, Winter Park 32789 $1,875,000 · 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
• 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 $1,999,990 · 4 bd · 4 ba · 3,330 sqft
• 1525 granville drive, Winter Park 32789 $4,595,000 · 5 bd · 6 ba · 5,211 sqft
• 361 east kings way, Winter Park 32789 $3,199,000 · 4 bd · 5 ba · 3,737 sqft
• 1840 bryan avenue, Winter Park 32789 $1,725,000 · 4 bd · 4 ba · 3,727 sqft
• 1420 aloma avenue, Winter Park 32789 $1,949,500 · 3 bd · 4 ba · 2,422 sqft
• 857 brock street, Winter Park 32789 $4,650,000 · 5 bd · 6 ba · 4,827 sqft
• 2407 lafayette avenue, Winter Park 32789 $1,625,000 · 5 bd · 5 ba · 3,133 sqft
• 2308 mulbry drive, Winter Park 32789 $1,699,000 · 4 bd · 4 ba · 2,530 sqft
• 620 virginia drive, Winter Park 32789 $3,890,000 · 6 bd · 5 ba · 4,677 sqft
• 2343 versailles avenue, Winter Park 32789 $1,750,000 · 4 bd · 4 ba · 3,307 sqft
• 648 worthington drive, Winter Park 32789 $2,700,000 · 5 bd · 5 ba · 3,588 sqft
• 720 pansy avenue, Winter Park 32789 $1,295,000 · 3 bd · 4 ba · 2,191 sqft
• 1526 miller avenue, Winter Park 32789 $1,574,900 · 5 bd · 5 ba · 3,252 sqft
• 150 east reading way, Winter Park 32789 $1,449,000 · 3 bd · 3 ba · 2,080 sqft
• 276 detmar drive, Winter Park 32789 $3,600,000 · 4 bd · 5 ba · 4,202 sqft
• 1550 palm avenue, Winter Park 32789 $1,829,000 · 4 bd · 4 ba · 2,706 sqft
• 751 pansy avenue, Winter Park 32789 $1,950,000 · 3 bd · 4 ba · 2,703 sqft
• 1761 legion drive, Winter Park 32789 $3,265,000 · 5 bd · 6 ba · 4,924 sqft
• 2207 kindel avenue, Winter Park 32789 $1,600,000 · 3 bd · 3 ba · 2,733 sqft
• 2430 chantilly avenue, Winter Park 32789 $1,598,000 · 4 bd · 4 ba · 2,916 sqft
• 1220 howell branch road, Winter Park 32789 $1,050,000 · 3 bd · 2 ba · 1,487 sqft
• 1445 via sangro place, Winter Park 32792 $1,350,000 · 6 bd · 6 ba · 5,021 sqft
• 160 west rockwood way, Winter Park 32789 $3,395,000 · 5 bd · 6 ba · 4,015 sqft
• 443 broadview avenue, Winter Park 32789 $1,095,000 · 4 bd · 3 ba · 2,803 sqft
• 702 via bella, Winter Park 32789 $4,400,000 · 4 bd · 6 ba · 3,720 sqft
• 1702 arbor park drive, Winter Park 32789 $1,900,000 · 4 bd · 4 ba · 2,950 sqft
• 2227 howard drive, Winter Park 32789 $1,100,000 · 3 bd · 3 ba · 2,196 sqft
• 1320 orchid avenue, Winter Park 32789 $1,350,000 · 4 bd · 4 ba · 2,998 sqft
• 901 golfview terrace, Winter Park 32789 $6,995,000 · 5 bd · 6 ba · 5,479 sqft