2 Bedroom Homes in Winter Park, FL

59 for sale · 112 homes listed · Updated September 25, 2026 · Page 1 of 3

• 151 north orlando avenue 118, Winter Park 32789 $299,999 · 2 bd · 1 ba · 710 sqft
• 3370 cedar springs place 156, Winter Park 32792 $182,500 · 2 bd · 3 ba · 1,031 sqft
• 2336 sun valley circle bldg 20, Winter Park 32792 $285,000 · 2 bd · 2 ba · 1,669 sqft
• 7471 canford court 19, Winter Park 32792 $199,000 · 2 bd · 2 ba · 1,393 sqft
• 151 north orlando avenue #115, Winter Park 32789 $285,000 · 2 bd · 1 ba · 710 sqft
• 560 ololu drive, Winter Park 32789 $899,000 · 2 bd · 2 ba · 1,086 sqft
• 230 strathy lane, Winter Park 32792 $499,000 · 2 bd · 1 ba · 920 sqft
• 205 lewfield circle 205, Winter Park 32792 $182,900 · 2 bd · 2 ba · 927 sqft
• 3220 netherwood drive, Winter Park 32792 $268,950 · 2 bd · 2 ba · 1,036 sqft
• 2918 antique oaks circle 25, Winter Park 32792 $189,000 · 2 bd · 2 ba · 1,018 sqft
• 3027 aaron burr avenue l1, Winter Park 32792 $159,000 · 2 bd · 3 ba · 1,090 sqft
• 7300 daniel webster drive m7, Winter Park 32792 $159,000 · 2 bd · 3 ba · 1,108 sqft
• 1695 lee road d211, Winter Park 32789 $107,000 · 2 bd · 1 ba · 881 sqft
• 5143 lazy oaks drive 5143, Winter Park 32792 $275,000 · 2 bd · 2 ba · 1,008 sqft
• 2317 sun valley circle 2317, Winter Park 32792 $267,000 · 2 bd · 2 ba · 1,295 sqft
• 7429 daniel webster drive 14 #c, Winter Park 32792 $133,000 · 2 bd · 2 ba · 1,036 sqft
• 7327 forest hill court 223, Winter Park 32792 $175,000 · 2 bd · 3 ba · 1,031 sqft
• 3243 forest oaks court 117, Winter Park 32792 $172,000 · 2 bd · 2 ba · 990 sqft
• 2923 antique oaks circle 34, Winter Park 32792 $180,000 · 2 bd · 2 ba · 1,105 sqft
• 193 lewfield circle, Winter Park 32792 $248,900 · 2 bd · 3 ba · 1,300 sqft
• 2500 lee road 220, Winter Park 32789 $199,900 · 2 bd · 1 ba · 851 sqft
• 1500 gay road 3c, Winter Park 32789 $235,000 · 2 bd · 2 ba · 1,026 sqft
• 2712 tortoise cove, Winter Park 32792 $235,000 · 2 bd · 1 ba · 924 sqft
• 7488 whisperwood drive 28, Winter Park 32792 $199,000 · 2 bd · 3 ba · 1,578 sqft
• 981 aragon avenue, Winter Park 32789 $494,999 · 2 bd · 1 ba · 857 sqft
• 2372 sun valley circle 2372, Winter Park 32792 $285,000 · 2 bd · 2 ba · 1,495 sqft
• 2305 sun valley circle, Winter Park 32792 $279,900 · 2 bd · 2 ba · 1,295 sqft
• 5184 lazy oaks drive, Winter Park 32792 $275,000 · 2 bd · 2 ba · 1,008 sqft
• 7450 wynnewood square 189, Winter Park 32792 $185,000 · 2 bd · 3 ba · 1,031 sqft
• 2475 tahoe circle, Winter Park 32792 $278,000 · 2 bd · 2 ba · 1,295 sqft
• 5210 lazy oaks drive, Winter Park 32792 $289,900 · 2 bd · 3 ba · 1,236 sqft
• 1071 aragon avenue, Winter Park 32789 $575,000 · 2 bd · 3 ba · 1,851 sqft
• 283 sandlewood trail 3, Winter Park 32789 $285,000 · 2 bd · 3 ba · 960 sqft
• 2477 tahoe circle 2477, Winter Park 32792 $254,000 · 2 bd · 2 ba · 1,316 sqft
• 1250 south denning drive unit 233, Winter Park 32789 $245,000 · 2 bd · 2 ba · 913 sqft
• 1431 palm avenue, Winter Park 32789 $825,000 · 2 bd · 2 ba · 1,540 sqft
• 7468 canford court 24, Winter Park 32792 $184,900 · 2 bd · 2 ba · 1,365 sqft
• 250 carolina avenue 205, Winter Park 32789 $739,000 · 2 bd · 2 ba · 1,311 sqft
• 311 east morse boulevard 4-5, Winter Park 32789 $975,000 · 2 bd · 2 ba · 1,763 sqft
• 623 grenadine court 623, Winter Park 32792 $194,900 · 2 bd · 2 ba · 1,037 sqft
• 2824 prince john road, Winter Park 32792 $475,000 · 2 bd · 2 ba · 1,438 sqft
• 222 lewfield circle, Winter Park 32792 $189,900 · 2 bd · 2 ba · 953 sqft
• 151 north orlando avenue 242, Winter Park 32789 $269,000 · 2 bd · 1 ba · 710 sqft
• 1259 indiana avenue, Winter Park 32789 $575,000 · 2 bd · 3 ba · 1,648 sqft
• 5108 lazy oaks drive 5108, Winter Park 32792 $269,000 · 2 bd · 2 ba · 1,008 sqft
• 3651 north goldenrod road c205, Winter Park 32792 $159,900 · 2 bd · 2 ba · 840 sqft
• 3020 antique oaks circle 129, Winter Park 32792 $135,000 · 2 bd · 2 ba · 1,018 sqft
• 500 north pennsylvania avenue g, Winter Park 32789 $349,500 · 2 bd · 1 ba · 709 sqft
• 1250 south denning drive 127, Winter Park 32789 $245,000 · 2 bd · 2 ba · 908 sqft
• 3651 north goldenrod road c109, Winter Park 32792 $165,000 · 2 bd · 2 ba · 840 sqft