Single Family Homes in Winter Park, FL

168 for sale · 599 homes listed · Updated September 27, 2026 · Page 7 of 12

• 2333 westminster court, Winter Park 32789 Active Under Contract $649,900 · 4 bd · 2 ba · 1,877 sqft
• 1941 oglesby avenue, Winter Park 32789 Active Under Contract $340,000 · 2 bd · 1 ba · 780 sqft
• 1313 south denning drive, Winter Park 32789 Active Under Contract $589,900 · 3 bd · 2 ba · 1,700 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
• 5334 lanyard court, Winter Park 32792 Active Under Contract $479,900 · 3 bd · 2 ba · 1,561 sqft
• 2873 old castle drive, Winter Park 32792 Active Under Contract $1,395,000 · 4 bd · 4 ba · 4,247 sqft
• 2825 mulford avenue, Winter Park 32789 Active Under Contract $629,000 · 2 bd · 2 ba · 1,249 sqft
• 7 carver court, Winter Park 32789 Active Under Contract $589,000 · 3 bd · 2 ba · 1,384 sqft
• 5218 lake howell road, Winter Park 32792 Active Under Contract $355,000 · 4 bd · 2 ba · 1,582 sqft
• 4599 whimbrel place, Winter Park 32792 Active Under Contract $675,000 · 4 bd · 3 ba · 2,366 sqft
• 1818 dover road, Winter Park 32792 Active Under Contract $439,900 · 3 bd · 2 ba · 1,873 sqft
• 2614 parkland drive, Winter Park 32789 Off market since Jul 2026 $1,894,000 · 4 bd · 4 ba · 3,307 sqft
• 5331 oak court, Winter Park 32792 Off market since Sep 2026 $460,000 · 3 bd · 2 ba · 1,263 sqft
• 2758 banchory road, Winter Park 32792 Off market since Sep 2026 $639,000 · 3 bd · 3 ba · 1,539 sqft
• 240 orange terrace drive, Winter Park 32789 Off market since Jul 2026 $470,000 · 4 bd · 2 ba · 1,718 sqft
• 1849 viburnum lane, Winter Park 32792 Off market since Sep 2026 $389,900 · 4 bd · 2 ba · 1,627 sqft
• 346 south ranger boulevard, Winter Park 32792 Off market since Aug 2026 $475,000 · 3 bd · 2 ba · 1,592 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
• 2612 roxbury road, Winter Park 32789 Off market since Sep 2026 $629,900 · 5 bd · 3 ba · 2,472 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
• 560 ololu drive, Winter Park 32789 Off market since Sep 2026 $899,000 · 2 bd · 2 ba · 1,086 sqft
• 1780 bryan avenue, Winter Park 32789 Off market since Jul 2026 $849,000 · 4 bd · 2 ba · 1,617 sqft
• 2217 sussex road, Winter Park 32792 Off market since Sep 2026 $485,000 · 4 bd · 2 ba · 2,092 sqft
• 1523 miller avenue, Winter Park 32789 Off market since Sep 2026 $1,399,000 · 5 bd · 4 ba · 3,164 sqft
• 230 strathy lane, Winter Park 32792 Off market since Sep 2026 $499,000 · 2 bd · 1 ba · 920 sqft
• 423 ololu drive, Winter Park 32789 Off market since Jul 2026 $549,000 · 3 bd · 3 ba · 1,920 sqft
• 2231 nairn drive, Winter Park 32792 Off market since Sep 2026 $499,000 · 3 bd · 2 ba · 1,088 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
• 1052 manchester circle, Winter Park 32792 Off market since Sep 2026 $460,000 · 3 bd · 2 ba · 1,703 sqft
• 330 elkhorn court, Winter Park 32792 Off market since Sep 2026 $544,900 · 3 bd · 2 ba · 1,570 sqft
• 1751 goodrich avenue, Winter Park 32789 Off market since Sep 2026 $1,380,000 · 4 bd · 4 ba · 2,170 sqft
• 1113 via del mar, Winter Park 32789 Off market since Sep 2026 $1,595,000 · 3 bd · 2 ba · 2,012 sqft
• 1521 heron wood place, Winter Park 32792 Off market since Sep 2026 $829,500 · 4 bd · 2 ba · 3,950 sqft
• 40 palmer avenue, Winter Park 32789 Off market since Sep 2026 $7,250,000 · 5 bd · 6 ba · 5,905 sqft
• 1927 eland avenue, Winter Park 32789 Off market since Sep 2026 $820,000 · 5 bd · 3 ba · 2,242 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
• 1260 alabama drive, Winter Park 32789 Off market since Sep 2026 $6,900,000 · 6 bd · 7 ba · 6,396 sqft
• 2708 lion heart road, Winter Park 32792 Off market since Sep 2026 $614,500 · 3 bd · 2 ba · 1,785 sqft
• 1354 indiana avenue, Winter Park 32789 Off market since Sep 2026 $574,900 · 3 bd · 2 ba · 1,269 sqft
• 604 balfour drive, Winter Park 32792 Off market since Sep 2026 $430,000 · 4 bd · 2 ba · 1,296 sqft
• 1581 forest avenue, Winter Park 32789 Off market since Sep 2026 $3,275,000 · 4 bd · 6 ba · 4,683 sqft
• lot #21 karolina avenue, Winter Park 32789 Off market since Sep 2026 $918,000 · 4 bd · 3 ba · 2,662 sqft
• 501 heritage boulevard, Winter Park 32792 Off market since Sep 2026 $419,000 · 4 bd · 2 ba · 1,376 sqft
• 609 south phelps avenue, Winter Park 32789 Off market since Jul 2026 $2,829,000 · 5 bd · 5 ba · 4,018 sqft