Homes under $500K in Winter Park, FL

97 for sale · 367 homes listed · Updated September 27, 2026 · Page 3 of 8

• 1760 peruvian lane, Winter Park 32792 Pending $324,000 · 3 bd · 2 ba · 1,160 sqft
• 1807 hammerlin avenue g, Winter Park 32789 Pending $499,000 · 3 bd · 3 ba · 1,818 sqft
• 758 warrenton road, Winter Park 32792 Pending $318,985 · 3 bd · 2 ba · 1,196 sqft
• 3282 oak lake place 3282, Winter Park 32792 Pending $154,500 · 2 bd · 2 ba · 990 sqft
• 2973 sanbina street, Winter Park 32789 Pending $377,880 · 3 bd · 2 ba · 1,128 sqft
• 1850 aster drive, Winter Park 32792 Pending $485,000 · 4 bd · 3 ba · 1,656 sqft
• 2500 lee road 104, Winter Park 32789 Pending $242,400 · 2 bd · 2 ba · 956 sqft
• 1521 cavendish road, Winter Park 32789 Pending $470,000 · 2 bd · 1 ba · 1,036 sqft
• 751 warrenton road, Winter Park 32792 Pending $319,900 · 3 bd · 2 ba · 1,196 sqft
• 644 north knowles avenue 3, Winter Park 32789 Pending $424,400 · 1 bd · 1 ba · 767 sqft
• 7509 glenmoor lane, Winter Park 32792 Pending $499,500 · 3 bd · 2 ba · 2,067 sqft
• 7500 waunatta court, Winter Park 32792 Pending $299,900 · 3 bd · 2 ba · 1,998 sqft
• 3621 hawthorne lane, Winter Park 32792 Pending $415,000 · 3 bd · 2 ba · 1,525 sqft
• 1695 lee road b108, Winter Park 32789 Pending $88,999 · 1 bd · 1 ba · 638 sqft
• 5781 shale court, Winter Park 32792 Pending $300,000 · 2 bd · 2 ba · 1,086 sqft
• 2223 conifer avenue, Winter Park 32792 Pending $435,000 · 3 bd · 2 ba · 1,620 sqft
• 3373 cedar springs place 149, Winter Park 32792 Pending $171,900 · 2 bd · 3 ba · 1,031 sqft
• 3321 royal street, Winter Park 32792 Pending $280,000 · 3 bd · 2 ba · 1,197 sqft
• 2511 eastbrook boulevard, Winter Park 32792 Pending $365,000 · 3 bd · 2 ba · 1,520 sqft
• 7026 hammock way, Winter Park 32792 Pending $362,000 · 3 bd · 2 ba · 1,257 sqft
• 2560 franklin avenue, Winter Park 32789 Pending $479,000 · 4 bd · 2 ba · 1,514 sqft
• 5444 peaco place, Winter Park 32792 Pending $250,000 · 2 bd · 2 ba · 924 sqft
• 7261 abbey lane, Winter Park 32792 Pending $350,000 · 3 bd · 2 ba · 1,268 sqft
• 2653 cayman way, Winter Park 32792 Pending $284,000 · 3 bd · 2 ba · 1,284 sqft
• 3328 hamlet loop, Winter Park 32792 Pending $349,900 · 3 bd · 2 ba · 1,397 sqft
• 1533 springtime loop, Winter Park 32792 Pending $415,000 · 3 bd · 2 ba · 1,192 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
• 2015 taylor avenue, Winter Park 32792 Pending $430,000 · 3 bd · 2 ba · 1,439 sqft
• 1484 viburnum lane, Winter Park 32792 Pending $295,000 · 3 bd · 2 ba · 1,363 sqft
• 720 killarney bay court 7-6, Winter Park 32789 Pending $389,000 · 2 bd · 2 ba · 1,140 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
• 3463 arnel drive, Winter Park 32792 Active Under Contract $404,900 · 3 bd · 2 ba · 1,770 sqft
• 3054 bluebrook drive, Winter Park 32792 Active Under Contract $389,500 · 3 bd · 2 ba · 1,939 sqft
• 639 saint johns court 639, Winter Park 32792 Active Under Contract $194,900 · 2 bd · 2 ba · 1,120 sqft
• 3374 hamlet loop, Winter Park 32792 Active Under Contract $355,000 · 3 bd · 3 ba · 1,397 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
• 440 cambridge boulevard, Winter Park 32789 Active Under Contract $369,900 · 2 bd · 1 ba · 988 sqft