Homes under $300K in Winter Park, FL

43 for sale · 180 homes listed · Updated September 27, 2026 · Page 2 of 4

• 5444 peaco place, Winter Park 32792 Pending $250,000 · 2 bd · 2 ba · 924 sqft
• 2653 cayman way, Winter Park 32792 Pending $284,000 · 3 bd · 2 ba · 1,284 sqft
• 1333 south denning drive, Winter Park 32789 Pending $299,000 · 2 bd · 1 ba · 702 sqft
• 1915 carrigan avenue, Winter Park 32792 Pending $299,900 · 3 bd · 1 ba · 1,520 sqft
• 2168 ridge drive, Winter Park 32792 Pending $299,000 · 3 bd · 1 ba · 1,208 sqft
• 2313 knoll street, Winter Park 32792 Pending $299,000 · 3 bd · 2 ba · 1,235 sqft
• 1484 viburnum lane, Winter Park 32792 Pending $295,000 · 3 bd · 2 ba · 1,363 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
• 3019 antique oaks circle 124, Winter Park 32792 Active Under Contract $139,500 · 1 bd · 1 ba · 749 sqft
• 311 east morse boulevard 7-11, Winter Park 32789 Active Under Contract $279,000 · 1 bd · 1 ba · 570 sqft
• 1695 lee road e204, Winter Park 32789 Active Under Contract $108,000 · 2 bd · 1 ba · 881 sqft
• 291 lewfield circle 291, Winter Park 32792 Active Under Contract $144,000 · 1 bd · 1 ba · 678 sqft
• 1695 lee road e215, Winter Park 32789 Active Under Contract $135,000 · 3 bd · 2 ba · 1,149 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
• 3371 river view way 46, Winter Park 32792 Active Under Contract $205,000 · 3 bd · 3 ba · 1,151 sqft
• 1695 lee road b210, Winter Park 32789 Active Under Contract $89,000 · 1 bd · 1 ba · 638 sqft
• 2500 lee road 232, Winter Park 32789 Active Under Contract $149,000 · 1 bd · 1 ba · 645 sqft
• 1500 gay road 17d, Winter Park 32789 Active Under Contract $234,900 · 2 bd · 2 ba · 1,026 sqft
• 311 east morse boulevard 6-12, Winter Park 32789 Active Under Contract $275,000 · 1 bd · 1 ba · 570 sqft
• 4798 tangerine avenue 4798, Winter Park 32792 Active Under Contract $175,000 · 2 bd · 2 ba · 1,058 sqft
• 3037 antique oaks circle 156, Winter Park 32792 Active Under Contract $154,900 · 1 bd · 1 ba · 749 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
• 1695 lee road a116, Winter Park 32789 Active Under Contract $135,000 · 3 bd · 2 ba · 1,149 sqft
• 283 lewfield circle 283, Winter Park 32792 Active Under Contract $142,500 · 1 bd · 1 ba · 678 sqft
• 145 scottsdale square, Winter Park 32792 Active Under Contract $99,900 · 2 bd · 2 ba · 1,020 sqft
• 2433 grand teton circle, Winter Park 32792 Active Under Contract $259,000 · 3 bd · 3 ba · 1,720 sqft
• 200 saint andrews boulevard 2904, Winter Park 32792 Active Under Contract $230,000 · 2 bd · 2 ba · 1,219 sqft
• 7340 swallow run 7340, Winter Park 32792 Active Under Contract $145,000 · 2 bd · 2 ba · 802 sqft
• 7487 canford court 5, Winter Park 32792 Active Under Contract $249,900 · 4 bd · 3 ba · 1,611 sqft
• 3651 north goldenrod road a103, Winter Park 32792 Active Under Contract $164,900 · 2 bd · 2 ba · 840 sqft
• 3014 antique oaks circle 120, Winter Park 32792 Active Under Contract $148,000 · 1 bd · 1 ba · 749 sqft
• 2657 exuma way, Winter Park 32792 Active Under Contract $285,000 · 3 bd · 2 ba · 1,467 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
• 2948 antique oaks circle 94, Winter Park 32792 Off market since Sep 2026 $150,000 · 1 bd · 1 ba · 749 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
• 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
• 2500 lee road 222, Winter Park 32789 Off market since Sep 2026 $184,400 · 1 bd · 1 ba · 645 sqft
• 205 lewfield circle 205, Winter Park 32792 Off market since Sep 2026 $182,900 · 2 bd · 2 ba · 927 sqft
• 3220 netherwood drive, Winter Park 32792 Off market since Sep 2026 $268,950 · 2 bd · 2 ba · 1,036 sqft
• 311 east morse boulevard 7-19, Winter Park 32789 Off market since Aug 2026 $284,900 · 1 bd · 1 ba · 482 sqft