2 Bedroom Homes in Winter Park, FL

50 for sale · 155 homes listed · Updated November 9, 2026 · Page 2 of 4

• 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
• 5143 Lazy Oaks Drive #5143, Winter Park 32792 Pending $275,000 · 2 bd · 2 ba · 1,008 sqft
• 3020 Antique Oaks Circle #129, Winter Park 32792 Pending $135,000 · 2 bd · 2 ba · 1,018 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
• 250 Carolina Avenue #205, Winter Park 32789 Active Under Contract $739,000 · 2 bd · 2 ba · 1,311 sqft
• 3651 North Goldenrod Road #C109, Winter Park 32792 Active Under Contract $165,000 · 2 bd · 2 ba · 840 sqft
• 7468 Canford Court #24, Winter Park 32792 Active Under Contract $184,900 · 2 bd · 2 ba · 1,365 sqft
• 2824 Prince John Road, Winter Park 32792 Active Under Contract $475,000 · 2 bd · 2 ba · 1,438 sqft
• 7302 Swallow Run #7302, Winter Park 32792 Active Under Contract $134,900 · 2 bd · 2 ba · 756 sqft
• 2302 Barbados Drive, Winter Park 32792 Active Under Contract $275,000 · 2 bd · 2 ba · 1,544 sqft
• 602 Trinidad Court #602, Winter Park 32792 Active Under Contract $227,000 · 2 bd · 2 ba · 1,120 sqft
• 5210 Lazy Oaks Drive, Winter Park 32792 Active Under Contract $274,900 · 2 bd · 3 ba · 1,236 sqft
• 640 North Park Avenue #3, Winter Park 32789 Active Under Contract $745,000 · 2 bd · 2 ba · 897 sqft
• 170 Balfour Drive #1, Winter Park 32792 Active Under Contract $299,000 · 2 bd · 2 ba · 1,032 sqft
• 151 North Orlando Avenue 118, Winter Park 32789 Off market since Sep 2026 $299,999 · 2 bd · 1 ba · 710 sqft