Homes under $300K in Winter Park, FL
74 for sale · 138 homes listed · Updated September 27, 2026 · Page 1 of 3
- 1695 lee road c202, Winter Park 32789 $205,000 · 3 bd · 2 ba · 1,149 sqft
- 3071 george mason avenue 5, Winter Park 32792 $89,900 · 1 bd · 1 ba · 549 sqft
- 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
- 2948 antique oaks circle 94, Winter Park 32792 $150,000 · 1 bd · 1 ba · 749 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
- 311 scottsdale square 311, Winter Park 32792 $109,400 · 1 bd · 1 ba · 785 sqft
- 151 north orlando avenue #115, Winter Park 32789 $285,000 · 2 bd · 1 ba · 710 sqft
- 2500 lee road 222, Winter Park 32789 $184,400 · 1 bd · 1 ba · 645 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
- 151 north orlando avenue 142, Winter Park 32789 $199,900 · 1 bd · 1 ba · 582 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
- 1000 south semoran boulevard 306, Winter Park 32792 $138,000 · 1 bd · 1 ba · 796 sqft
- 1000 south semoran boulevard 408, Winter Park 32792 $138,000 · 1 bd · 1 ba · 776 sqft
- 1000 south semoran boulevard 404, Winter Park 32792 $138,000 · 1 bd · 1 ba · 776 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
- 1250 south denning drive 109, Winter Park 32789 $190,000 · 1 bd · 1 ba · 658 sqft
- 2450 grand teton circle 2450, Winter Park 32792 $250,000 · 3 bd · 2 ba · 1,311 sqft
- 2487 harbour way, Winter Park 32792 $270,000 · 3 bd · 3 ba · 1,803 sqft
- 1500 gay road 4d, Winter Park 32789 $164,500 · 1 bd · 1 ba · 732 sqft
- 7450 wynnewood square 189, Winter Park 32792 $185,000 · 2 bd · 3 ba · 1,031 sqft
- 1000 south semoran boulevard 305, Winter Park 32792 $115,000 · 1 bd · 1 ba · 735 sqft
- 2475 tahoe circle, Winter Park 32792 $278,000 · 2 bd · 2 ba · 1,295 sqft
- 1000 south semoran boulevard 302, Winter Park 32792 $110,000 · 1 bd · 1 ba · 796 sqft
- 1695 lee road a101, Winter Park 32789 $154,900 · 3 bd · 2 ba · 1,149 sqft
- 5210 lazy oaks drive, Winter Park 32792 $289,900 · 2 bd · 3 ba · 1,236 sqft
- 7413 belle river court 3, Winter Park 32792 $214,900 · 3 bd · 3 ba · 1,151 sqft
- 1695 lee road d107, Winter Park 32789 $180,000 · 1 bd · 1 ba · 638 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
- 7468 canford court 24, Winter Park 32792 $184,900 · 2 bd · 2 ba · 1,365 sqft