Homes under $1M in Winter Park, FL

157 for sale · 591 homes listed · Updated September 27, 2026 · Page 5 of 12

• 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
• 1592 arbor park drive, Winter Park 32789 Pending $700,000 · 4 bd · 3 ba · 2,016 sqft
• 1421 michigan avenue, Winter Park 32789 Pending $586,567 · 5 bd · 3 ba · 2,031 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
• 744 cornwall road, Winter Park 32792 Active Under Contract $630,000 · 4 bd · 2 ba · 1,968 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
• 1800 magnolia avenue, Winter Park 32789 Active Under Contract $950,000 · 4 bd · 3 ba · 2,431 sqft
• 3463 arnel drive, Winter Park 32792 Active Under Contract $404,900 · 3 bd · 2 ba · 1,770 sqft
• 512 north lakemont avenue, Winter Park 32792 Active Under Contract $500,000 · 3 bd · 2 ba · 1,413 sqft
• 3114 heartleaf place, Winter Park 32792 Active Under Contract $685,000 · 4 bd · 3 ba · 2,702 sqft
• 1507 golfside drive, Winter Park 32792 Active Under Contract $830,000 · 3 bd · 2 ba · 2,003 sqft
• 3054 bluebrook drive, Winter Park 32792 Active Under Contract $389,500 · 3 bd · 2 ba · 1,939 sqft
• 1830 edwin boulevard, Winter Park 32789 Active Under Contract $625,000 · 3 bd · 2 ba · 1,287 sqft
• 639 saint johns court 639, Winter Park 32792 Active Under Contract $194,900 · 2 bd · 2 ba · 1,120 sqft
• 1900 winter park road, Winter Park 32789 Active Under Contract $799,000 · 4 bd · 2 ba · 1,511 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
• 1438 tierra circle, Winter Park 32792 Active Under Contract $514,900 · 3 bd · 2 ba · 1,627 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
• 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
• 1009 lake bell drive, Winter Park 32789 Active Under Contract $650,000 · 3 bd · 2 ba · 1,467 sqft
• 1540 florentino lane, Winter Park 32792 Active Under Contract $315,000 · 3 bd · 3 ba · 1,682 sqft
• 1120 wisconsin avenue, Winter Park 32789 Active Under Contract $999,000 · 3 bd · 4 ba · 2,213 sqft
• 241 west lake sue avenue, Winter Park 32789 Active Under Contract $995,000 · 3 bd · 3 ba · 2,304 sqft
• 2803 banchory road, Winter Park 32792 Active Under Contract $474,000 · 4 bd · 2 ba · 1,596 sqft
• 2157 lake drive, Winter Park 32789 Active Under Contract $689,000 · 3 bd · 3 ba · 2,124 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
• 840 west canton avenue, Winter Park 32789 Active Under Contract $649,900 · 3 bd · 2 ba · 1,370 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
• 2831 mulford avenue, Winter Park 32789 Active Under Contract $635,000 · 4 bd · 3 ba · 1,647 sqft
• 528 saint dunstan way, Winter Park 32792 Active Under Contract $524,990 · 3 bd · 2 ba · 1,656 sqft
• 275 north ranger boulevard, Winter Park 32792 Active Under Contract $759,000 · 4 bd · 3 ba · 1,950 sqft
• 2700 cady way, Winter Park 32792 Active Under Contract $649,000 · 4 bd · 2 ba · 1,876 sqft
• 3641 hawthorne lane, Winter Park 32792 Active Under Contract $449,990 · 3 bd · 2 ba · 1,622 sqft