Single Family Homes in Winter Park, FL

168 for sale · 599 homes listed · Updated September 27, 2026 · Page 5 of 12

• 1905 bonanza court, Winter Park 32792 Pending $520,000 · 4 bd · 2 ba · 1,774 sqft
• 1246 verdant glade place, Winter Park 32792 Pending $765,000 · 4 bd · 4 ba · 2,137 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
• 1117 wading waters circle, Winter Park 32792 Pending $1,325,000 · 6 bd · 4 ba · 4,307 sqft
• 1597 oakhurst avenue, Winter Park 32789 Pending $2,699,000 · 5 bd · 5 ba · 4,410 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
• 1592 arbor park drive, Winter Park 32789 Pending $700,000 · 4 bd · 3 ba · 2,016 sqft
• 570 manor road, Winter Park 32751 Active Under Contract $12,500,000 · 6 bd · 10 ba · 10,172 sqft
• 1150 via salerno, Winter Park 32789 Active Under Contract $3,750,000 · 4 bd · 6 ba · 3,826 sqft
• 501 lakeview avenue, Winter Park 32789 Active Under Contract $1,390,000 · 4 bd · 5 ba · 3,253 sqft
• 744 cornwall road, Winter Park 32792 Active Under Contract $630,000 · 4 bd · 2 ba · 1,968 sqft
• 607 ellen drive, Winter Park 32789 Active Under Contract $1,389,500 · 4 bd · 5 ba · 2,812 sqft
• 2501 winter park road, Winter Park 32789 Active Under Contract $1,649,000 · 5 bd · 4 ba · 3,304 sqft
• 1870 walker avenue, Winter Park 32789 Active Under Contract $1,199,000 · 3 bd · 3 ba · 2,046 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
• 721 pansy avenue, Winter Park 32789 Active Under Contract $1,850,000 · 4 bd · 4 ba · 2,653 sqft
• 1649 harmon avenue, Winter Park 32789 Active Under Contract $1,250,000 · 4 bd · 4 ba · 3,223 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
• 1130 park north place, Winter Park 32789 Active Under Contract $2,200,000 · 5 bd · 4 ba · 4,011 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
• 802 hamilton place court, Winter Park 32789 Active Under Contract $1,295,000 · 4 bd · 4 ba · 2,843 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
• 1981 blue ridge road, Winter Park 32789 Active Under Contract $1,150,000 · 4 bd · 2 ba · 2,750 sqft
• 1813 harland park drive, Winter Park 32789 Active Under Contract $1,875,000 · 4 bd · 4 ba · 3,551 sqft
• 1438 tierra circle, Winter Park 32792 Active Under Contract $514,900 · 3 bd · 2 ba · 1,627 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
• 1009 lake bell drive, Winter Park 32789 Active Under Contract $650,000 · 3 bd · 2 ba · 1,467 sqft
• 1120 wisconsin avenue, Winter Park 32789 Active Under Contract $999,000 · 3 bd · 4 ba · 2,213 sqft
• 1420 magnolia avenue, Winter Park 32789 Active Under Contract $1,690,000 · 4 bd · 4 ba · 3,174 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
• 5530 south lake burkett lane, Winter Park 32792 Active Under Contract $430,000 · 3 bd · 3 ba · 1,669 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
• 426 worthington drive, Winter Park 32789 Active Under Contract $2,499,000 · 5 bd · 5 ba · 3,520 sqft