Homes under $500K in Winter Park, FL

97 for sale · 367 homes listed · Updated September 27, 2026 · Page 4 of 8

• 1914 bonanza court, Winter Park 32792 Active Under Contract $429,999 · 3 bd · 2 ba · 1,727 sqft
• 1500 gay road 17d, Winter Park 32789 Active Under Contract $234,900 · 2 bd · 2 ba · 1,026 sqft
• 1540 florentino lane, Winter Park 32792 Active Under Contract $315,000 · 3 bd · 3 ba · 1,682 sqft
• 2803 banchory road, Winter Park 32792 Active Under Contract $474,000 · 4 bd · 2 ba · 1,596 sqft
• 2006 cornell avenue, Winter Park 32789 Active Under Contract $328,000 · 2 bd · 1 ba · 797 sqft
• 7577 dockside street, Winter Park 32792 Active Under Contract $360,000 · 3 bd · 2 ba · 1,245 sqft
• 311 east morse boulevard 6-12, Winter Park 32789 Active Under Contract $275,000 · 1 bd · 1 ba · 570 sqft
• 5530 south lake burkett lane, Winter Park 32792 Active Under Contract $430,000 · 3 bd · 3 ba · 1,669 sqft
• 4798 tangerine avenue 4798, Winter Park 32792 Active Under Contract $175,000 · 2 bd · 2 ba · 1,058 sqft
• 1662 tremont lane, Winter Park 32792 Active Under Contract $384,900 · 3 bd · 2 ba · 1,534 sqft
• 3641 hawthorne lane, Winter Park 32792 Active Under Contract $449,990 · 3 bd · 2 ba · 1,622 sqft
• 2521 galliano circle, Winter Park 32792 Active Under Contract $335,000 · 3 bd · 3 ba · 1,682 sqft
• 3037 antique oaks circle 156, Winter Park 32792 Active Under Contract $154,900 · 1 bd · 1 ba · 749 sqft
• 3381 cedar springs place 151, Winter Park 32792 Active Under Contract $179,900 · 2 bd · 3 ba · 1,031 sqft
• 1610 gladiolas drive, Winter Park 32792 Active Under Contract $399,800 · 4 bd · 2 ba · 1,808 sqft
• 3060 george mason d, Winter Park 32792 Active Under Contract $107,000 · 2 bd · 2 ba · 1,062 sqft
• 2022 eastbrook boulevard, Winter Park 32792 Active Under Contract $353,000 · 3 bd · 2 ba · 1,240 sqft
• 4887 north magnolia avenue, Winter Park 32792 Active Under Contract $495,000 · 4 bd · 3 ba · 1,955 sqft
• 1695 lee road a116, Winter Park 32789 Active Under Contract $135,000 · 3 bd · 2 ba · 1,149 sqft
• 283 lewfield circle 283, Winter Park 32792 Active Under Contract $142,500 · 1 bd · 1 ba · 678 sqft
• 1189 lazy hollow place, Winter Park 32792 Active Under Contract $445,000 · 4 bd · 2 ba · 1,525 sqft
• 4965 orange avenue, Winter Park 32792 Active Under Contract $370,000 · 4 bd · 2 ba · 1,444 sqft
• 145 scottsdale square, Winter Park 32792 Active Under Contract $99,900 · 2 bd · 2 ba · 1,020 sqft
• 846 driver avenue, Winter Park 32789 Active Under Contract $325,000 · 2 bd · 1 ba · 824 sqft
• 1456 east brookshire court, Winter Park 32792 Active Under Contract $449,000 · 3 bd · 2 ba · 1,673 sqft
• 2433 grand teton circle, Winter Park 32792 Active Under Contract $259,000 · 3 bd · 3 ba · 1,720 sqft
• 200 saint andrews boulevard 2904, Winter Park 32792 Active Under Contract $230,000 · 2 bd · 2 ba · 1,219 sqft
• 7426 blue jacket place east, Winter Park 32792 Active Under Contract $324,900 · 3 bd · 2 ba · 1,150 sqft
• 2826 ambergate road, Winter Park 32792 Active Under Contract $460,000 · 3 bd · 2 ba · 1,521 sqft
• 2323 devon court, Winter Park 32789 Active Under Contract $429,000 · 4 bd · 2 ba · 2,403 sqft
• 351 starling road, Winter Park 32789 Active Under Contract $499,900 · 3 bd · 2 ba · 1,979 sqft
• 7340 swallow run 7340, Winter Park 32792 Active Under Contract $145,000 · 2 bd · 2 ba · 802 sqft
• 7487 canford court 5, Winter Park 32792 Active Under Contract $249,900 · 4 bd · 3 ba · 1,611 sqft
• 3651 north goldenrod road a103, Winter Park 32792 Active Under Contract $164,900 · 2 bd · 2 ba · 840 sqft
• 3014 antique oaks circle 120, Winter Park 32792 Active Under Contract $148,000 · 1 bd · 1 ba · 749 sqft
• 1427 broad wing lane, Winter Park 32792 Active Under Contract $419,900 · 3 bd · 3 ba · 2,312 sqft
• 642 warrenton road, Winter Park 32792 Active Under Contract $300,000 · 2 bd · 2 ba · 1,362 sqft
• 4963 tangerine avenue, Winter Park 32792 Active Under Contract $375,000 · 4 bd · 2 ba · 1,822 sqft
• 7640 village green drive, Winter Park 32792 Active Under Contract $439,000 · 3 bd · 2 ba · 1,631 sqft
• 2765 abbey road, Winter Park 32792 Active Under Contract $430,000 · 3 bd · 2 ba · 1,620 sqft
• 1011 manchester circle, Winter Park 32792 Active Under Contract $450,000 · 4 bd · 2 ba · 1,699 sqft
• 1941 oglesby avenue, Winter Park 32789 Active Under Contract $340,000 · 2 bd · 1 ba · 780 sqft
• 2657 exuma way, Winter Park 32792 Active Under Contract $285,000 · 3 bd · 2 ba · 1,467 sqft
• 5334 lanyard court, Winter Park 32792 Active Under Contract $479,900 · 3 bd · 2 ba · 1,561 sqft
• 1521 bantam way, Winter Park 32792 Active Under Contract $424,900 · 3 bd · 3 ba · 1,755 sqft
• 5218 lake howell road, Winter Park 32792 Active Under Contract $355,000 · 4 bd · 2 ba · 1,582 sqft
• 1818 dover road, Winter Park 32792 Active Under Contract $439,900 · 3 bd · 2 ba · 1,873 sqft
• 1695 lee road c202, Winter Park 32789 Off market since Sep 2026 $205,000 · 3 bd · 2 ba · 1,149 sqft
• 3071 george mason avenue 5, Winter Park 32792 Off market since Sep 2026 $89,900 · 1 bd · 1 ba · 549 sqft
• 151 north orlando avenue 118, Winter Park 32789 Off market since Sep 2026 $299,999 · 2 bd · 1 ba · 710 sqft