2 Bedroom Homes in Winter Park, FL

59 for sale · 112 homes listed · Updated September 25, 2026 · Page 2 of 3

• 2302 barbados drive, Winter Park 32792 $295,000 · 2 bd · 2 ba · 1,544 sqft
• 7476 woodburn court 38, Winter Park 32792 $170,000 · 2 bd · 3 ba · 1,031 sqft
• 2383 sun valley circle 2383, Winter Park 32792 $234,900 · 2 bd · 2 ba · 1,295 sqft
• 447 north phelps avenue, Winter Park 32789 $960,000 · 2 bd · 1 ba · 1,290 sqft
• 7302 swallow run 7302, Winter Park 32792 $134,900 · 2 bd · 2 ba · 756 sqft
• 7453 daniel webster drive a5, Winter Park 32792 $150,000 · 2 bd · 2 ba · 1,063 sqft
• 1306 south pennsylvania avenue 5, Winter Park 32789 $359,000 · 2 bd · 1 ba · 830 sqft
• 602 trinidad court 602, Winter Park 32792 $227,000 · 2 bd · 2 ba · 1,120 sqft
• 192 balfour drive 2, Winter Park 32792 $319,000 · 2 bd · 2 ba · 1,287 sqft
• 2651 cayman way, Winter Park 32792 Pending $255,000 · 2 bd · 2 ba · 1,020 sqft
• 630 killarney bay court 3, Winter Park 32789 Pending $475,000 · 2 bd · 3 ba · 1,428 sqft
• 3282 oak lake place 3282, Winter Park 32792 Pending $154,500 · 2 bd · 2 ba · 990 sqft
• 2500 lee road 104, Winter Park 32789 Pending $242,400 · 2 bd · 2 ba · 956 sqft
• 1521 cavendish road, Winter Park 32789 Pending $470,000 · 2 bd · 1 ba · 1,036 sqft
• 5781 shale court, Winter Park 32792 Pending $300,000 · 2 bd · 2 ba · 1,086 sqft
• 3373 cedar springs place 149, Winter Park 32792 Pending $171,900 · 2 bd · 3 ba · 1,031 sqft
• 5444 peaco place, Winter Park 32792 Pending $250,000 · 2 bd · 2 ba · 924 sqft
• 1333 south denning drive, Winter Park 32789 Pending $299,000 · 2 bd · 1 ba · 702 sqft
• 720 killarney bay court 7-6, Winter Park 32789 Pending $389,000 · 2 bd · 2 ba · 1,140 sqft
• 2500 lee road 202, Winter Park 32789 Active Under Contract $224,999 · 2 bd · 2 ba · 956 sqft
• 2500 lee road 208, Winter Park 32789 Active Under Contract $175,000 · 2 bd · 2 ba · 956 sqft
• 1695 lee road e204, Winter Park 32789 Active Under Contract $108,000 · 2 bd · 1 ba · 881 sqft
• 1500 gay road 20d, Winter Park 32789 Active Under Contract $245,000 · 2 bd · 2 ba · 1,026 sqft
• 7336 forest hill court 240, Winter Park 32792 Active Under Contract $163,500 · 2 bd · 2 ba · 990 sqft
• 639 saint johns court 639, Winter Park 32792 Active Under Contract $194,900 · 2 bd · 2 ba · 1,120 sqft
• 440 cambridge boulevard, Winter Park 32789 Active Under Contract $369,900 · 2 bd · 1 ba · 988 sqft
• 311 east morse boulevard 1-3, Winter Park 32789 Active Under Contract $1,825,000 · 2 bd · 2 ba · 2,304 sqft
• 1500 gay road 17d, Winter Park 32789 Active Under Contract $234,900 · 2 bd · 2 ba · 1,026 sqft
• 2006 cornell avenue, Winter Park 32789 Active Under Contract $328,000 · 2 bd · 1 ba · 797 sqft
• 1600 alabama drive 402, Winter Park 32789 Active Under Contract $1,250,000 · 2 bd · 2 ba · 1,574 sqft
• 4798 tangerine avenue 4798, Winter Park 32792 Active Under Contract $175,000 · 2 bd · 2 ba · 1,058 sqft
• 3381 cedar springs place 151, Winter Park 32792 Active Under Contract $179,900 · 2 bd · 3 ba · 1,031 sqft
• 3060 george mason d, Winter Park 32792 Active Under Contract $107,000 · 2 bd · 2 ba · 1,062 sqft
• 1122 washington avenue 7b, Winter Park 32789 Active Under Contract $575,000 · 2 bd · 3 ba · 1,556 sqft
• 2824 woodside avenue, Winter Park 32789 Active Under Contract $600,000 · 2 bd · 2 ba · 912 sqft
• 145 scottsdale square, Winter Park 32792 Active Under Contract $99,900 · 2 bd · 2 ba · 1,020 sqft
• 846 driver avenue, Winter Park 32789 Active Under Contract $325,000 · 2 bd · 1 ba · 824 sqft
• 200 saint andrews boulevard 2904, Winter Park 32792 Active Under Contract $230,000 · 2 bd · 2 ba · 1,219 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
• 3651 north goldenrod road a103, Winter Park 32792 Active Under Contract $164,900 · 2 bd · 2 ba · 840 sqft
• 2881 temple trail, Winter Park 32789 Active Under Contract $575,000 · 2 bd · 3 ba · 1,704 sqft
• 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
• 1941 oglesby avenue, Winter Park 32789 Active Under Contract $340,000 · 2 bd · 1 ba · 780 sqft
• 2825 mulford avenue, Winter Park 32789 Active Under Contract $629,000 · 2 bd · 2 ba · 1,249 sqft
• 1500 harris circle, Winter Park 32789 Off market since Jul 2026 $1,195,000 · 2 bd · 3 ba · 2,096 sqft
• 2648 galliano circle, Winter Park 32792 Off market since Jul 2026 $355,000 · 2 bd · 3 ba · 1,550 sqft
• 277 scottsdale square 277, Winter Park 32792 Off market since Sep 2026 $99,000 · 2 bd · 2 ba · 1,020 sqft
• 1695 lee road e103, Winter Park 32789 Off market since Aug 2026 $129,900 · 2 bd · 1 ba · 881 sqft