Homes under $1M in Winter Park, FL

157 for sale · 591 homes listed · Updated September 27, 2026 · Page 6 of 12

• 2521 galliano circle, Winter Park 32792 Active Under Contract $335,000 · 3 bd · 3 ba · 1,682 sqft
• 3037 antique oaks circle 156, Winter Park 32792 Active Under Contract $154,900 · 1 bd · 1 ba · 749 sqft
• 1037 north virginia avenue, Winter Park 32789 Active Under Contract $649,000 · 3 bd · 1 ba · 1,101 sqft
• 3381 cedar springs place 151, Winter Park 32792 Active Under Contract $179,900 · 2 bd · 3 ba · 1,031 sqft
• 1610 gladiolas drive, Winter Park 32792 Active Under Contract $399,800 · 4 bd · 2 ba · 1,808 sqft
• 3060 george mason d, Winter Park 32792 Active Under Contract $107,000 · 2 bd · 2 ba · 1,062 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
• 1695 lee road a116, Winter Park 32789 Active Under Contract $135,000 · 3 bd · 2 ba · 1,149 sqft
• 1122 washington avenue 7b, Winter Park 32789 Active Under Contract $575,000 · 2 bd · 3 ba · 1,556 sqft
• 283 lewfield circle 283, Winter Park 32792 Active Under Contract $142,500 · 1 bd · 1 ba · 678 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
• 786 mcintyre avenue, Winter Park 32789 Active Under Contract $625,000 · 3 bd · 3 ba · 1,934 sqft
• 4437 glenmoor court, Winter Park 32792 Active Under Contract $525,000 · 3 bd · 2 ba · 2,633 sqft
• 145 scottsdale square, Winter Park 32792 Active Under Contract $99,900 · 2 bd · 2 ba · 1,020 sqft
• 1871 barker drive, Winter Park 32789 Active Under Contract $779,000 · 3 bd · 3 ba · 2,231 sqft
• 1134 washington avenue 13c, Winter Park 32789 Active Under Contract $525,000 · 3 bd · 4 ba · 2,195 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
• 2833 prince john road, Winter Park 32792 Active Under Contract $669,000 · 4 bd · 2 ba · 1,605 sqft
• 2433 grand teton circle, Winter Park 32792 Active Under Contract $259,000 · 3 bd · 3 ba · 1,720 sqft
• 200 saint andrews boulevard 2904, Winter Park 32792 Active Under Contract $230,000 · 2 bd · 2 ba · 1,219 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
• 2552 brookshire avenue, Winter Park 32792 Active Under Contract $530,000 · 3 bd · 2 ba · 1,314 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
• 7340 swallow run 7340, Winter Park 32792 Active Under Contract $145,000 · 2 bd · 2 ba · 802 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
• 7487 canford court 5, Winter Park 32792 Active Under Contract $249,900 · 4 bd · 3 ba · 1,611 sqft
• 3651 north goldenrod road a103, Winter Park 32792 Active Under Contract $164,900 · 2 bd · 2 ba · 840 sqft
• 3014 antique oaks circle 120, Winter Park 32792 Active Under Contract $148,000 · 1 bd · 1 ba · 749 sqft
• 2881 temple trail, Winter Park 32789 Active Under Contract $575,000 · 2 bd · 3 ba · 1,704 sqft
• 1427 broad wing lane, Winter Park 32792 Active Under Contract $419,900 · 3 bd · 3 ba · 2,312 sqft