2 Bedroom Homes in Winter Park, FL

36 for sale · 147 homes listed · Updated September 27, 2026 · Page 3 of 3

• 193 lewfield circle, Winter Park 32792 Off market since Sep 2026 $248,900 · 2 bd · 3 ba · 1,300 sqft
• 2500 lee road 220, Winter Park 32789 Off market since Sep 2026 $199,900 · 2 bd · 1 ba · 851 sqft
• 4756 tangerine avenue 4756, Winter Park 32792 Off market since Sep 2026 $185,000 · 2 bd · 2 ba · 1,058 sqft
• 1500 gay road 3c, Winter Park 32789 Off market since Sep 2026 $235,000 · 2 bd · 2 ba · 1,026 sqft
• 7733 country place g2, Winter Park 32792 Off market since Aug 2026 $229,500 · 2 bd · 2 ba · 1,068 sqft
• 2712 tortoise cove, Winter Park 32792 Off market since Sep 2026 $235,000 · 2 bd · 1 ba · 924 sqft
• 7488 whisperwood drive 28, Winter Park 32792 Off market since Sep 2026 $199,000 · 2 bd · 3 ba · 1,578 sqft
• 981 aragon avenue, Winter Park 32789 Off market since Sep 2026 $494,999 · 2 bd · 1 ba · 857 sqft
• 2372 sun valley circle 2372, Winter Park 32792 Off market since Sep 2026 $285,000 · 2 bd · 2 ba · 1,495 sqft
• 252 scottsdale square 252, Winter Park 32792 Off market since Sep 2026 $85,000 · 2 bd · 2 ba · 1,085 sqft
• 2305 sun valley circle, Winter Park 32792 Off market since Sep 2026 $279,900 · 2 bd · 2 ba · 1,295 sqft
• 5184 lazy oaks drive, Winter Park 32792 Off market since Sep 2026 $275,000 · 2 bd · 2 ba · 1,008 sqft
• 3360 royal street, Winter Park 32792 Off market since Jul 2026 $179,900 · 2 bd · 2 ba · 981 sqft
• 303 scottsdale square 303, Winter Park 32792 Off market since Sep 2026 $80,000 · 2 bd · 2 ba · 1,020 sqft
• 263 scottsdale square 263, Winter Park 32792 Off market since Sep 2026 $80,000 · 2 bd · 2 ba · 1,020 sqft
• 7450 wynnewood square 189, Winter Park 32792 Off market since Sep 2026 $170,000 · 2 bd · 3 ba · 1,031 sqft
• 2475 tahoe circle, Winter Park 32792 Off market since Sep 2026 $268,000 · 2 bd · 2 ba · 1,295 sqft
• 5210 lazy oaks drive, Winter Park 32792 Off market since Sep 2026 $279,900 · 2 bd · 3 ba · 1,236 sqft
• 1071 aragon avenue, Winter Park 32789 Off market since Sep 2026 $575,000 · 2 bd · 3 ba · 1,851 sqft
• 283 sandlewood trail 3, Winter Park 32789 Off market since Sep 2026 $285,000 · 2 bd · 3 ba · 960 sqft
• 3651 north goldenrod road 206, Winter Park 32792 Off market since Sep 2026 $179,900 · 2 bd · 2 ba · 840 sqft
• 2477 tahoe circle 2477, Winter Park 32792 Off market since Sep 2026 $254,000 · 2 bd · 2 ba · 1,316 sqft
• 1250 south denning drive unit 233, Winter Park 32789 Off market since Sep 2026 $245,000 · 2 bd · 2 ba · 913 sqft
• 1431 palm avenue, Winter Park 32789 Off market since Sep 2026 $825,000 · 2 bd · 2 ba · 1,540 sqft
• 7468 canford court 24, Winter Park 32792 Off market since Sep 2026 $184,900 · 2 bd · 2 ba · 1,365 sqft
• 250 carolina avenue 205, Winter Park 32789 Off market since Sep 2026 $739,000 · 2 bd · 2 ba · 1,311 sqft
• 311 east morse boulevard 4-5, Winter Park 32789 Off market since Sep 2026 $975,000 · 2 bd · 2 ba · 1,763 sqft
• 623 grenadine court 623, Winter Park 32792 Off market since Sep 2026 $194,900 · 2 bd · 2 ba · 1,037 sqft
• 2824 prince john road, Winter Park 32792 Off market since Sep 2026 $475,000 · 2 bd · 2 ba · 1,438 sqft
• 222 lewfield circle, Winter Park 32792 Off market since Sep 2026 $189,900 · 2 bd · 2 ba · 953 sqft
• 151 north orlando avenue 242, Winter Park 32789 Off market since Sep 2026 $269,000 · 2 bd · 1 ba · 710 sqft
• 1259 indiana avenue, Winter Park 32789 Off market since Sep 2026 $575,000 · 2 bd · 3 ba · 1,648 sqft
• 5108 lazy oaks drive 5108, Winter Park 32792 Off market since Sep 2026 $269,000 · 2 bd · 2 ba · 1,008 sqft
• 3651 north goldenrod road c205, Winter Park 32792 Off market since Sep 2026 $159,900 · 2 bd · 2 ba · 840 sqft
• 3020 antique oaks circle 129, Winter Park 32792 Off market since Sep 2026 $135,000 · 2 bd · 2 ba · 1,018 sqft
• 500 north pennsylvania avenue g, Winter Park 32789 Off market since Sep 2026 $349,500 · 2 bd · 1 ba · 709 sqft
• 1250 south denning drive 127, Winter Park 32789 Off market since Sep 2026 $245,000 · 2 bd · 2 ba · 908 sqft
• 3651 north goldenrod road c109, Winter Park 32792 Off market since Sep 2026 $165,000 · 2 bd · 2 ba · 840 sqft
• 2302 barbados drive, Winter Park 32792 Off market since Sep 2026 $295,000 · 2 bd · 2 ba · 1,544 sqft
• 7476 woodburn court 38, Winter Park 32792 Off market since Sep 2026 $170,000 · 2 bd · 3 ba · 1,031 sqft
• 2383 sun valley circle 2383, Winter Park 32792 Off market since Sep 2026 $234,900 · 2 bd · 2 ba · 1,295 sqft
• 447 north phelps avenue, Winter Park 32789 Off market since Sep 2026 $960,000 · 2 bd · 1 ba · 1,290 sqft
• 7302 swallow run 7302, Winter Park 32792 Off market since Sep 2026 $134,900 · 2 bd · 2 ba · 756 sqft
• 7453 daniel webster drive a5, Winter Park 32792 Off market since Sep 2026 $150,000 · 2 bd · 2 ba · 1,063 sqft
• 1306 south pennsylvania avenue 5, Winter Park 32789 Off market since Sep 2026 $359,000 · 2 bd · 1 ba · 830 sqft
• 602 trinidad court 602, Winter Park 32792 Off market since Sep 2026 $227,000 · 2 bd · 2 ba · 1,120 sqft
• 192 balfour drive 2, Winter Park 32792 Off market since Sep 2026 $319,000 · 2 bd · 2 ba · 1,287 sqft