Homes under $1M in Winter Park, FL

157 for sale · 591 homes listed · Updated September 27, 2026 · Page 7 of 12

• 642 warrenton road, Winter Park 32792 Active Under Contract $300,000 · 2 bd · 2 ba · 1,362 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
• 1011 manchester circle, Winter Park 32792 Active Under Contract $450,000 · 4 bd · 2 ba · 1,699 sqft
• 565 huntington avenue 565, Winter Park 32789 Active Under Contract $635,000 · 3 bd · 3 ba · 2,015 sqft
• 1621 chestnut avenue, Winter Park 32789 Active Under Contract $899,000 · 3 bd · 3 ba · 2,022 sqft
• 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
• 2657 exuma way, Winter Park 32792 Active Under Contract $285,000 · 3 bd · 2 ba · 1,467 sqft
• 5334 lanyard court, Winter Park 32792 Active Under Contract $479,900 · 3 bd · 2 ba · 1,561 sqft
• 1521 bantam way, Winter Park 32792 Active Under Contract $424,900 · 3 bd · 3 ba · 1,755 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
• 1695 lee road c202, Winter Park 32789 Off market since Sep 2026 $205,000 · 3 bd · 2 ba · 1,149 sqft
• 3071 george mason avenue 5, Winter Park 32792 Off market since Sep 2026 $89,900 · 1 bd · 1 ba · 549 sqft
• 151 north orlando avenue 118, Winter Park 32789 Off market since Sep 2026 $299,999 · 2 bd · 1 ba · 710 sqft
• 3370 cedar springs place 156, Winter Park 32792 Off market since Sep 2026 $179,990 · 2 bd · 3 ba · 1,031 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
• 2948 antique oaks circle 94, Winter Park 32792 Off market since Sep 2026 $150,000 · 1 bd · 1 ba · 749 sqft
• 346 south ranger boulevard, Winter Park 32792 Off market since Aug 2026 $475,000 · 3 bd · 2 ba · 1,592 sqft
• 2336 sun valley circle bldg 20, Winter Park 32792 Off market since Sep 2026 $285,000 · 2 bd · 2 ba · 1,669 sqft
• 7471 canford court 19, Winter Park 32792 Off market since Sep 2026 $199,000 · 2 bd · 2 ba · 1,393 sqft
• 311 scottsdale square 311, Winter Park 32792 Off market since Sep 2026 $109,400 · 1 bd · 1 ba · 785 sqft
• 2612 roxbury road, Winter Park 32789 Off market since Sep 2026 $629,900 · 5 bd · 3 ba · 2,472 sqft
• 7470 canford court 23, Winter Park 32792 Off market since Jul 2026 $245,900 · 3 bd · 3 ba · 1,580 sqft
• 151 north orlando avenue #115, Winter Park 32789 Off market since Sep 2026 $285,000 · 2 bd · 1 ba · 710 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
• 2500 lee road 222, Winter Park 32789 Off market since Sep 2026 $184,400 · 1 bd · 1 ba · 645 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
• 205 lewfield circle 205, Winter Park 32792 Off market since Sep 2026 $182,900 · 2 bd · 2 ba · 927 sqft
• 1809 hammerlin avenue, Winter Park 32789 Off market since Jul 2026 $549,000 · 3 bd · 3 ba · 1,818 sqft
• 3220 netherwood drive, Winter Park 32792 Off market since Sep 2026 $268,950 · 2 bd · 2 ba · 1,036 sqft
• 432 west swoope avenue, Winter Park 32789 Off market since Sep 2026 $680,000 · 4 bd · 4 ba · 2,664 sqft
• 311 east morse boulevard 7-19, Winter Park 32789 Off market since Aug 2026 $284,900 · 1 bd · 1 ba · 482 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