Homes under $400K in Winter Park, FL
102 for sale · 195 homes listed · Updated September 25, 2026 · Page 2 of 4
- 2526 passamonte drive 10f, Winter Park 32792 $335,000 · 3 bd · 3 ba · 1,790 sqft
- 2568 lotafun avenue, Winter Park 32789 $395,000 · 3 bd · 2 ba · 1,201 sqft
- 2033 canny cove, Winter Park 32792 $389,000 · 3 bd · 3 ba · 1,907 sqft
- 3562 bougainvillea drive, Winter Park 32792 $334,000 · 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 $110,000 · 1 bd · 1 ba · 796 sqft
- 1695 lee road a101, Winter Park 32789 $154,900 · 3 bd · 2 ba · 1,149 sqft
- 2017 canny cove, Winter Park 32792 $389,900 · 3 bd · 3 ba · 1,907 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
- 310 granada drive, Winter Park 32789 $339,900 · 3 bd · 2 ba · 1,344 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
- 2857 clever lane, Winter Park 32792 $399,995 · 3 bd · 3 ba · 1,782 sqft
- 3019 antique oaks circle 127, Winter Park 32792 $143,500 · 1 bd · 1 ba · 749 sqft
- 623 grenadine court 623, Winter Park 32792 $194,900 · 2 bd · 2 ba · 1,037 sqft
- 285 lewfield circle 285, Winter Park 32792 $147,000 · 1 bd · 1 ba · 678 sqft
- 151 north orlando avenue 261, Winter Park 32789 $219,999 · 1 bd · 1 ba · 582 sqft
- 7605 aloma pines court, Winter Park 32792 $359,000 · 3 bd · 3 ba · 1,872 sqft
- 222 lewfield circle, Winter Park 32792 $189,900 · 2 bd · 2 ba · 953 sqft
- 3302 royal street, Winter Park 32792 $274,900 · 3 bd · 2 ba · 1,197 sqft
- 151 north orlando avenue 242, Winter Park 32789 $269,000 · 2 bd · 1 ba · 710 sqft
- 5108 lazy oaks drive 5108, Winter Park 32792 $269,000 · 2 bd · 2 ba · 1,008 sqft
- 7530 cranes creek court, Winter Park 32792 $309,900 · 3 bd · 3 ba · 1,545 sqft
- 3651 north goldenrod road c205, Winter Park 32792 $159,900 · 2 bd · 2 ba · 840 sqft
- 7506 cranes creek court 30, Winter Park 32792 $365,000 · 3 bd · 3 ba · 1,861 sqft
- 2500 lee road 143, Winter Park 32789 $130,000 · 1 bd · 1 ba · 645 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
- 2122 ridge drive, Winter Park 32792 $360,000 · 4 bd · 3 ba · 1,664 sqft
- 2275 island run, Winter Park 32792 $299,990 · 3 bd · 2 ba · 1,467 sqft
- 2626 ambergate road, Winter Park 32792 $380,000 · 3 bd · 1 ba · 1,143 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
- 2136 linden road, Winter Park 32792 $365,000 · 3 bd · 2 ba · 1,185 sqft
- 2302 barbados drive, Winter Park 32792 $295,000 · 2 bd · 2 ba · 1,544 sqft
- 7476 woodburn court 38, Winter Park 32792 $170,000 · 2 bd · 3 ba · 1,031 sqft
- 2383 sun valley circle 2383, Winter Park 32792 $234,900 · 2 bd · 2 ba · 1,295 sqft
- 4870 seminole avenue, Winter Park 32792 $380,000 · 3 bd · 2 ba · 1,277 sqft
- 7302 swallow run 7302, Winter Park 32792 $134,900 · 2 bd · 2 ba · 756 sqft
- 5080 seminole avenue, Winter Park 32792 $299,900 · 3 bd · 2 ba · 1,078 sqft
- 2463 grand teton circle 2463, Winter Park 32792 $249,000 · 3 bd · 3 ba · 1,720 sqft
- 3484 seagrape drive, Winter Park 32792 $299,900 · 4 bd · 2 ba · 1,227 sqft
- 7453 daniel webster drive a5, Winter Park 32792 $150,000 · 2 bd · 2 ba · 1,063 sqft
- 1306 south pennsylvania avenue 5, Winter Park 32789 $359,000 · 2 bd · 1 ba · 830 sqft
- 7348 grand avenue, Winter Park 32792 $285,000 · 3 bd · 2 ba · 1,509 sqft