Single Family Homes in Winter Park, FL

168 for sale · 599 homes listed · Updated September 27, 2026 · Page 6 of 12

• 3641 hawthorne lane, Winter Park 32792 Active Under Contract $449,990 · 3 bd · 2 ba · 1,622 sqft
• 1037 north virginia avenue, Winter Park 32789 Active Under Contract $649,000 · 3 bd · 1 ba · 1,101 sqft
• 1610 gladiolas drive, Winter Park 32792 Active Under Contract $399,800 · 4 bd · 2 ba · 1,808 sqft
• 2022 eastbrook boulevard, Winter Park 32792 Active Under Contract $353,000 · 3 bd · 2 ba · 1,240 sqft
• 4887 north magnolia avenue, Winter Park 32792 Active Under Contract $495,000 · 4 bd · 3 ba · 1,955 sqft
• 2361 roxbury road, Winter Park 32789 Active Under Contract $599,000 · 3 bd · 2 ba · 1,723 sqft
• 1189 lazy hollow place, Winter Park 32792 Active Under Contract $445,000 · 4 bd · 2 ba · 1,525 sqft
• 729 monmouth way, Winter Park 32792 Active Under Contract $799,000 · 4 bd · 3 ba · 2,332 sqft
• 2087 laurelwood way, Winter Park 32792 Active Under Contract $625,000 · 4 bd · 2 ba · 1,920 sqft
• 2824 woodside avenue, Winter Park 32789 Active Under Contract $600,000 · 2 bd · 2 ba · 912 sqft
• 1908 cyril court, Winter Park 32792 Active Under Contract $639,000 · 4 bd · 3 ba · 2,471 sqft
• 4965 orange avenue, Winter Park 32792 Active Under Contract $370,000 · 4 bd · 2 ba · 1,444 sqft
• 2010 summerfield road, Winter Park 32792 Active Under Contract $575,000 · 3 bd · 2 ba · 1,889 sqft
• 2803 riddle drive, Winter Park 32789 Active Under Contract $525,000 · 3 bd · 3 ba · 1,709 sqft
• 1750 walnut avenue, Winter Park 32789 Active Under Contract $2,195,000 · 4 bd · 5 ba · 3,691 sqft
• 229 alexander place, Winter Park 32789 Active Under Contract $4,250,000 · 4 bd · 6 ba · 4,431 sqft
• 4437 glenmoor court, Winter Park 32792 Active Under Contract $525,000 · 3 bd · 2 ba · 2,633 sqft
• 1871 barker drive, Winter Park 32789 Active Under Contract $779,000 · 3 bd · 3 ba · 2,231 sqft
• 1351 oneco avenue, Winter Park 32789 Active Under Contract $1,150,000 · 4 bd · 3 ba · 2,474 sqft
• 846 driver avenue, Winter Park 32789 Active Under Contract $325,000 · 2 bd · 1 ba · 824 sqft
• 1456 east brookshire court, Winter Park 32792 Active Under Contract $449,000 · 3 bd · 2 ba · 1,673 sqft
• 1492 via sangro place, Winter Park 32792 Active Under Contract $920,000 · 4 bd · 3 ba · 3,063 sqft
• 216 blossom lane, Winter Park 32789 Active Under Contract $624,900 · 4 bd · 2 ba · 1,933 sqft
• 570 manor road maitland, Winter Park 32751 Active Under Contract $12,500,000 · 6 bd · 10 ba · 10,172 sqft
• 2833 prince john road, Winter Park 32792 Active Under Contract $669,000 · 4 bd · 2 ba · 1,605 sqft
• 7426 blue jacket place east, Winter Park 32792 Active Under Contract $324,900 · 3 bd · 2 ba · 1,150 sqft
• 2826 ambergate road, Winter Park 32792 Active Under Contract $460,000 · 3 bd · 2 ba · 1,521 sqft
• 2323 devon court, Winter Park 32789 Active Under Contract $429,000 · 4 bd · 2 ba · 2,403 sqft
• 433 gilbert road, Winter Park 32792 Active Under Contract $669,900 · 3 bd · 2 ba · 1,800 sqft
• 2525 temple drive, Winter Park 32789 Active Under Contract $4,750,000 · 5 bd · 5 ba · 4,542 sqft
• 2138 talman court, Winter Park 32792 Active Under Contract $1,450,000 · 4 bd · 5 ba · 4,249 sqft
• 2552 brookshire avenue, Winter Park 32792 Active Under Contract $530,000 · 3 bd · 2 ba · 1,314 sqft
• 645 pansy avenue, Winter Park 32789 Active Under Contract $2,390,000 · 4 bd · 5 ba · 3,661 sqft
• 351 starling road, Winter Park 32789 Active Under Contract $499,900 · 3 bd · 2 ba · 1,979 sqft
• 2781 abbey road, Winter Park 32792 Active Under Contract $520,000 · 3 bd · 2 ba · 1,596 sqft
• 531 west swoope avenue, Winter Park 32789 Active Under Contract $635,000 · 2 bd · 2 ba · 1,188 sqft
• 890 north phelps avenue, Winter Park 32789 Active Under Contract $1,775,000 · 4 bd · 5 ba · 3,630 sqft
• 913 camellia avenue, Winter Park 32789 Active Under Contract $655,000 · 3 bd · 3 ba · 1,389 sqft
• 110 longhorn road, Winter Park 32792 Active Under Contract $750,000 · 4 bd · 3 ba · 2,673 sqft
• 4033 tenita drive, Winter Park 32792 Active Under Contract $569,000 · 4 bd · 2 ba · 2,022 sqft
• 2719 woodside avenue, Winter Park 32789 Active Under Contract $610,000 · 3 bd · 2 ba · 1,431 sqft
• 948 poinciana lane, Winter Park 32789 Active Under Contract $2,750,000 · 4 bd · 5 ba · 3,676 sqft
• 1409 sunset drive, Winter Park 32789 Active Under Contract $649,000 · 2 bd · 2 ba · 1,107 sqft
• 4963 tangerine avenue, Winter Park 32792 Active Under Contract $375,000 · 4 bd · 2 ba · 1,822 sqft
• 7640 village green drive, Winter Park 32792 Active Under Contract $439,000 · 3 bd · 2 ba · 1,631 sqft
• 1287 verdant glade place, Winter Park 32792 Active Under Contract $745,000 · 4 bd · 4 ba · 3,020 sqft
• 2765 abbey road, Winter Park 32792 Active Under Contract $430,000 · 3 bd · 2 ba · 1,620 sqft
• 1417 williams drive, Winter Park 32789 Active Under Contract $3,999,000 · 5 bd · 6 ba · 4,891 sqft
• 1011 manchester circle, Winter Park 32792 Active Under Contract $450,000 · 4 bd · 2 ba · 1,699 sqft
• 1621 chestnut avenue, Winter Park 32789 Active Under Contract $899,000 · 3 bd · 3 ba · 2,022 sqft