Homes under $400K in Winter Park, FL
99 homes for sale · Updated August 12, 2026 · Page 2 of 2
- 2500 lee road 104, Winter Park 32789 $249,900 · 2 bd · 2 ba · 956 sqft
- 1605 puritan avenue, Winter Park 32792 $389,000 · 3 bd · 2 ba · 1,285 sqft
- 4756 tangerine avenue 4756, Winter Park 32792 $185,000 · 2 bd · 2 ba · 1,058 sqft
- 1500 gay road 3c, Winter Park 32789 $244,900 · 2 bd · 2 ba · 1,026 sqft
- 2339 inagua way, Winter Park 32792 $299,999 · 3 bd · 2 ba · 1,324 sqft
- 2712 tortoise cove, Winter Park 32792 $235,000 · 2 bd · 1 ba · 924 sqft
- 7488 whisperwood drive 28, Winter Park 32792 $210,000 · 2 bd · 3 ba · 1,578 sqft
- 2521 galliano circle, Winter Park 32792 $350,000 · 3 bd · 3 ba · 1,682 sqft
- 1610 gladiolas drive, Winter Park 32792 $399,800 · 4 bd · 2 ba · 1,808 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
- 1695 lee road a116, Winter Park 32789 $135,000 · 3 bd · 2 ba · 1,149 sqft
- 2372 sun valley circle 2372, Winter Park 32792 $285,000 · 2 bd · 2 ba · 1,495 sqft
- 252 scottsdale square 252, Winter Park 32792 $85,000 · 2 bd · 2 ba · 1,085 sqft
- 2305 sun valley circle, Winter Park 32792 $279,900 · 2 bd · 2 ba · 1,295 sqft
- 5184 lazy oaks drive, Winter Park 32792 $280,000 · 2 bd · 2 ba · 1,008 sqft
- 1250 south denning drive 109, Winter Park 32789 $190,000 · 1 bd · 1 ba · 658 sqft
- 1695 lee road b108, Winter Park 32789 $88,999 · 1 bd · 1 ba · 638 sqft
- 5781 shale court, Winter Park 32792 $315,000 · 2 bd · 2 ba · 1,086 sqft
- 4965 orange avenue, Winter Park 32792 $379,900 · 4 bd · 2 ba · 1,444 sqft
- 2450 grand teton circle 2450, Winter Park 32792 $255,000 · 3 bd · 2 ba · 1,311 sqft
- 303 scottsdale square 303, Winter Park 32792 $80,000 · 2 bd · 2 ba · 1,020 sqft
- 885 carnation drive, Winter Park 32792 $385,000 · 4 bd · 2 ba · 1,240 sqft
- 263 scottsdale square 263, Winter Park 32792 $80,000 · 2 bd · 2 ba · 1,020 sqft
- 2487 harbour way, Winter Park 32792 $290,000 · 3 bd · 3 ba · 1,803 sqft
- 1500 gay road 4d, Winter Park 32789 $169,900 · 1 bd · 1 ba · 732 sqft
- 7450 wynnewood square 189, Winter Park 32792 $185,000 · 2 bd · 3 ba · 1,031 sqft
- 2526 passamonte drive 10f, Winter Park 32792 $335,000 · 3 bd · 3 ba · 1,790 sqft
- 2033 canny cove, Winter Park 32792 $399,000 · 3 bd · 3 ba · 1,907 sqft
- 7340 daniel webster drive, Winter Park 32792 $179,900 · 3 bd · 2 ba
- 2433 grand teton circle, Winter Park 32792 $259,000 · 3 bd · 3 ba · 1,720 sqft
- 200 saint andrews boulevard 2904, Winter Park 32792 $230,000 · 2 bd · 2 ba · 1,219 sqft
- 3562 bougainvillea drive, Winter Park 32792 $339,000 · 3 bd · 2 ba · 1,149 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 $115,000 · 1 bd · 1 ba · 796 sqft
- 1695 lee road a101, Winter Park 32789 $154,900 · 3 bd · 2 ba · 1,149 sqft
- 7340 swallow run 7340, Winter Park 32792 $145,000 · 2 bd · 2 ba · 802 sqft
- 7261 abbey lane, Winter Park 32792 $350,000 · 3 bd · 2 ba · 1,268 sqft
- 2017 canny cove, Winter Park 32792 $399,900 · 3 bd · 3 ba · 1,907 sqft
- 5210 lazy oaks drive 5210, Winter Park 32792 $289,900 · 2 bd · 3 ba · 1,236 sqft
- 7413 belle river court 3, Winter Park 32792 $229,900 · 3 bd · 3 ba · 1,151 sqft
- 310 granada drive, Winter Park 32789 $354,999 · 3 bd · 2 ba · 1,344 sqft
- 1695 lee road d107, Winter Park 32789 $180,000 · 1 bd · 1 ba · 638 sqft
- 3328 hamlet loop, Winter Park 32792 $349,900 · 3 bd · 2 ba · 1,397 sqft
- 7487 canford court 5, Winter Park 32792 $249,900 · 2 bd · 3 ba · 1,611 sqft
- 3651 north goldenrod road 206, Winter Park 32792 $179,900 · 2 bd · 2 ba · 840 sqft
- 3651 north goldenrod road a103, Winter Park 32792 $164,900 · 2 bd · 2 ba · 840 sqft