Homes under $500K in Winter Park, FL
97 for sale · 367 homes listed · Updated September 27, 2026 · Page 7 of 8
- 1886 clematis lane, Winter Park 32792 Off market since Sep 2026 $425,000 · 3 bd · 2 ba · 1,238 sqft
- 2475 tahoe circle, Winter Park 32792 Off market since Sep 2026 $268,000 · 2 bd · 2 ba · 1,295 sqft
- 3740 hawthorne lane, Winter Park 32792 Off market since Sep 2026 $435,000 · 3 bd · 2 ba · 1,645 sqft
- 405 lake fair lane, Winter Park 32789 Sold on Sep 11, 2026 $434,990 · 3 bd · 2 ba
- 1000 south semoran boulevard 302, Winter Park 32792 Off market since Sep 2026 $110,000 · 1 bd · 1 ba · 796 sqft
- 1695 lee road a101, Winter Park 32789 Off market since Sep 2026 $154,900 · 3 bd · 2 ba · 1,149 sqft
- 2007 cornell avenue, Winter Park 32789 Off market since Sep 2026 $449,000 · 3 bd · 2 ba · 1,154 sqft
- 2017 canny cove, Winter Park 32792 Off market since Sep 2026 $389,900 · 3 bd · 3 ba · 1,907 sqft
- 5210 lazy oaks drive, Winter Park 32792 Off market since Sep 2026 $279,900 · 2 bd · 3 ba · 1,236 sqft
- 5316 halyard court, Winter Park 32792 Off market since Sep 2026 $495,000 · 3 bd · 2 ba · 1,380 sqft
- 7413 belle river court 3, Winter Park 32792 Off market since Sep 2026 $214,900 · 3 bd · 3 ba · 1,151 sqft
- 310 granada drive, Winter Park 32789 Off market since Sep 2026 $339,900 · 3 bd · 2 ba · 1,344 sqft
- 1695 lee road d107, Winter Park 32789 Off market since Sep 2026 $180,000 · 1 bd · 1 ba · 638 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
- 5588 garden grove circle, Winter Park 32792 Off market since Sep 2026 $400,000 · 3 bd · 2 ba · 1,310 sqft
- 2477 tahoe circle 2477, Winter Park 32792 Off market since Sep 2026 $254,000 · 2 bd · 2 ba · 1,316 sqft
- 1652 berkshire avenue, Winter Park 32789 Off market since Sep 2026 $479,000 · 3 bd · 2 ba · 1,498 sqft
- 1250 south denning drive unit 233, Winter Park 32789 Off market since Sep 2026 $245,000 · 2 bd · 2 ba · 913 sqft
- 7384 grand avenue, Winter Park 32792 Off market since Sep 2026 $425,000 · 3 bd · 2 ba · 1,162 sqft
- 1955 eland avenue, Winter Park 32789 Off market since Sep 2026 $410,000 · 3 bd · 2 ba · 1,494 sqft
- 7468 canford court 24, Winter Park 32792 Off market since Sep 2026 $184,900 · 2 bd · 2 ba · 1,365 sqft
- 1842 puritan avenue, Winter Park 32792 Off market since Sep 2026 $419,000 · 4 bd · 2 ba · 1,836 sqft
- 2857 clever lane, Winter Park 32792 Off market since Sep 2026 $399,995 · 3 bd · 3 ba · 1,782 sqft
- 3019 antique oaks circle 127, Winter Park 32792 Off market since Sep 2026 $143,500 · 1 bd · 1 ba · 749 sqft
- 2112 eastbrook boulevard, Winter Park 32792 Off market since Sep 2026 $423,000 · 3 bd · 2 ba · 1,470 sqft
- 623 grenadine court 623, Winter Park 32792 Off market since Sep 2026 $194,900 · 2 bd · 2 ba · 1,037 sqft
- 285 lewfield circle 285, Winter Park 32792 Off market since Sep 2026 $147,000 · 1 bd · 1 ba · 678 sqft
- 151 north orlando avenue 261, Winter Park 32789 Off market since Sep 2026 $219,999 · 1 bd · 1 ba · 582 sqft
- 7605 aloma pines court, Winter Park 32792 Off market since Sep 2026 $359,000 · 3 bd · 3 ba · 1,872 sqft
- 2824 prince john road, Winter Park 32792 Off market since Sep 2026 $475,000 · 2 bd · 2 ba · 1,438 sqft
- 2181 linden road, Winter Park 32792 Off market since Sep 2026 $450,000 · 5 bd · 3 ba · 1,442 sqft
- 222 lewfield circle, Winter Park 32792 Off market since Sep 2026 $189,900 · 2 bd · 2 ba · 953 sqft
- 2126 albert lee parkway, Winter Park 32789 Off market since Sep 2026 $415,000 · 3 bd · 2 ba · 1,187 sqft
- 3302 royal street, Winter Park 32792 Off market since Sep 2026 $274,900 · 3 bd · 2 ba · 1,197 sqft
- 151 north orlando avenue 242, Winter Park 32789 Off market since Sep 2026 $269,000 · 2 bd · 1 ba · 710 sqft
- 5108 lazy oaks drive 5108, Winter Park 32792 Off market since Sep 2026 $269,000 · 2 bd · 2 ba · 1,008 sqft
- 7530 cranes creek court, Winter Park 32792 Off market since Sep 2026 $309,900 · 3 bd · 3 ba · 1,545 sqft
- 3651 north goldenrod road c205, Winter Park 32792 Off market since Sep 2026 $159,900 · 2 bd · 2 ba · 840 sqft
- 7506 cranes creek court 30, Winter Park 32792 Off market since Sep 2026 $365,000 · 3 bd · 3 ba · 1,861 sqft
- 3020 nicholson drive, Winter Park 32792 Off market since Sep 2026 $495,000 · 4 bd · 2 ba · 1,756 sqft
- 2500 lee road 143, Winter Park 32789 Off market since Sep 2026 $130,000 · 1 bd · 1 ba · 645 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
- 2122 ridge drive, Winter Park 32792 Off market since Sep 2026 $360,000 · 4 bd · 3 ba · 1,664 sqft
- 2349 shadowland loop, Winter Park 32792 Off market since Sep 2026 $425,000 · 3 bd · 3 ba · 1,755 sqft
- 2275 island run, Winter Park 32792 Off market since Sep 2026 $299,990 · 3 bd · 2 ba · 1,467 sqft
- 2626 ambergate road, Winter Park 32792 Off market since Sep 2026 $380,000 · 3 bd · 1 ba · 1,143 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