4 Bedroom Homes in Winter Park, FL

105 for sale · 185 homes listed · Updated September 27, 2026 · Page 1 of 4

• 1849 viburnum lane, Winter Park 32792 $399,900 · 4 bd · 2 ba · 1,627 sqft
• 2217 sussex road, Winter Park 32792 $485,000 · 4 bd · 2 ba · 2,092 sqft
• 1840 anzle avenue, Winter Park 32789 $1,750,000 · 4 bd · 3 ba · 2,350 sqft
• 432 west swoope avenue, Winter Park 32789 $680,000 · 4 bd · 4 ba · 2,664 sqft
• 1751 goodrich avenue, Winter Park 32789 $1,380,000 · 4 bd · 4 ba · 2,170 sqft
• 1521 heron wood place, Winter Park 32792 $829,500 · 4 bd · 2 ba · 3,950 sqft
• 1581 forest avenue, Winter Park 32789 $3,275,000 · 4 bd · 6 ba · 4,683 sqft
• lot #21 karolina avenue, Winter Park 32789 $918,000 · 4 bd · 3 ba · 2,662 sqft
• 501 heritage boulevard, Winter Park 32792 $426,000 · 4 bd · 2 ba · 1,376 sqft
• 1903 north park avenue, Winter Park 32789 $1,649,000 · 4 bd · 4 ba · 2,807 sqft
• 905 enclave place, Winter Park 32792 $1,550,000 · 4 bd · 4 ba · 2,756 sqft
• 901 enclave place, Winter Park 32792 $1,550,000 · 4 bd · 4 ba · 2,738 sqft
• 1750 carollee lane, Winter Park 32789 $1,750,000 · 4 bd · 4 ba · 3,249 sqft
• 541 west canton avenue, Winter Park 32789 $2,495,000 · 4 bd · 4 ba · 3,553 sqft
• 1570 palmer avenue, Winter Park 32789 $1,595,000 · 4 bd · 4 ba · 3,048 sqft
• 1131 wildmeadow run, Winter Park 32792 $825,000 · 4 bd · 4 ba · 2,589 sqft
• 1090 wildmeadow run, Winter Park 32792 $835,000 · 4 bd · 4 ba · 2,589 sqft
• 1870 staunton avenue, Winter Park 32789 $1,250,000 · 4 bd · 4 ba · 2,525 sqft
• 1369 blue stem lane, Winter Park 32792 $775,000 · 4 bd · 4 ba · 2,589 sqft
• 102 bell place, Winter Park 32792 $1,299,000 · 4 bd · 4 ba · 2,459 sqft
• 1441 cardinal court, Winter Park 32789 $3,995,000 · 4 bd · 6 ba · 4,066 sqft
• 1611 chestnut avenue, Winter Park 32789 $995,000 · 4 bd · 4 ba · 2,916 sqft
• 446 melrose avenue, Winter Park 32789 $1,595,000 · 4 bd · 2 ba · 2,640 sqft
• 1606 miller avenue, Winter Park 32789 $1,249,900 · 4 bd · 4 ba · 2,936 sqft
• 2512 eastbrook boulevard, Winter Park 32792 $390,000 · 4 bd · 2 ba · 1,607 sqft
• 616 brechin drive, Winter Park 32792 $999,000 · 4 bd · 5 ba · 2,638 sqft
• 316 beckett court, Winter Park 32792 $450,000 · 4 bd · 2 ba · 1,651 sqft
• 1946 strathaven road, Winter Park 32792 $599,000 · 4 bd · 3 ba · 2,102 sqft
• 723 symonds avenue, Winter Park 32789 $1,700,000 · 4 bd · 4 ba · 3,065 sqft
• 1581 magnolia avenue, Winter Park 32789 $1,425,000 · 4 bd · 4 ba · 2,756 sqft
• 1320 gladiolas drive, Winter Park 32792 $469,900 · 4 bd · 2 ba · 1,624 sqft
• 1404 border drive, Winter Park 32789 $1,075,000 · 4 bd · 4 ba · 2,469 sqft
• 715 south ranger boulevard, Winter Park 32792 $695,000 · 4 bd · 3 ba · 2,312 sqft
• 2054 eastbrook boulevard, Winter Park 32792 $500,000 · 4 bd · 3 ba · 2,031 sqft
• 2240 venetian way, Winter Park 32789 $3,500,000 · 4 bd · 4 ba · 4,036 sqft
• 231 chelton circle, Winter Park 32789 $4,950,000 · 4 bd · 7 ba · 5,550 sqft
• 1421 chapman circle, Winter Park 32789 $1,377,500 · 4 bd · 4 ba · 3,578 sqft
• 8433 commander cove, Winter Park 32792 $455,000 · 4 bd · 3 ba · 1,903 sqft
• 1316 blue stem lane, Winter Park 32792 $725,000 · 4 bd · 3 ba · 2,196 sqft
• 2008 houndslake drive, Winter Park 32792 $475,000 · 4 bd · 2 ba · 2,250 sqft
• 313 sylvan drive, Winter Park 32789 $5,500,000 · 4 bd · 5 ba · 4,775 sqft
• 2015 summerfield road, Winter Park 32792 $1,262,500 · 4 bd · 4 ba · 3,024 sqft
• 1564 lawndale circle, Winter Park 32792 $450,000 · 4 bd · 3 ba · 1,980 sqft
• 4353 steed terrace, Winter Park 32792 $599,900 · 4 bd · 2 ba · 2,275 sqft
• 3006 northwood boulevard, Winter Park 32789 $950,000 · 4 bd · 3 ba · 2,075 sqft
• 341 east reading way, Winter Park 32789 $1,525,000 · 4 bd · 4 ba · 3,723 sqft
• 722 south ranger boulevard, Winter Park 32792 $775,000 · 4 bd · 3 ba · 2,164 sqft
• 436 west swoope avenue, Winter Park 32789 $699,000 · 4 bd · 4 ba · 2,602 sqft
• 885 carnation drive, Winter Park 32792 $368,000 · 4 bd · 2 ba · 1,240 sqft
• 1418 lone feather trail, Winter Park 32792 $699,500 · 4 bd · 3 ba · 2,197 sqft