4 Bedroom Homes in Winter Park, FL

67 for sale · 252 homes listed · Updated September 27, 2026 · Page 2 of 6

• 2008 houndslake drive, Winter Park 32792 $475,000 · 4 bd · 2 ba · 2,250 sqft
• 2211 king richards court, Winter Park 32792 $529,000 · 4 bd · 2 ba · 1,845 sqft
• 533 country club drive, Winter Park 32789 $1,599,000 · 4 bd · 4 ba · 2,942 sqft
• 1421 chapman circle, Winter Park 32789 $1,377,500 · 4 bd · 4 ba · 3,578 sqft
• 2430 chantilly avenue, Winter Park 32789 $1,598,000 · 4 bd · 4 ba · 2,916 sqft
• 1581 magnolia avenue, Winter Park 32789 $1,425,000 · 4 bd · 4 ba · 2,642 sqft
• 901 enclave place, Winter Park 32792 $1,550,000 · 4 bd · 4 ba · 2,738 sqft
• 2215 woodcrest drive, Winter Park 32792 $675,000 · 4 bd · 2 ba · 1,688 sqft
• 555 east lake sue avenue, Winter Park 32789 $2,095,000 · 4 bd · 4 ba · 3,776 sqft
• 2015 summerfield road, Winter Park 32792 $1,262,500 · 4 bd · 4 ba · 3,024 sqft
• 1951 winter park road, Winter Park 32789 $2,089,000 · 4 bd · 4 ba · 3,479 sqft
• 2054 eastbrook boulevard, Winter Park 32792 $500,000 · 4 bd · 3 ba · 2,031 sqft
• 885 carnation drive, Winter Park 32792 $368,000 · 4 bd · 2 ba · 1,240 sqft
• 952 moss lane, Winter Park 32789 $1,319,950 · 4 bd · 5 ba · 3,474 sqft
• 501 heritage boulevard, Winter Park 32792 $419,000 · 4 bd · 2 ba · 1,376 sqft
• 4353 steed terrace, Winter Park 32792 $599,900 · 4 bd · 2 ba · 2,275 sqft
• 7786 fox knoll place, Winter Park 32792 $410,500 · 4 bd · 2 ba · 1,301 sqft
• 2052 leanne court, Winter Park 32792 Pending $440,000 · 4 bd · 2 ba · 2,264 sqft
• 2228 howard drive, Winter Park 32789 Pending $2,460,000 · 4 bd · 4 ba · 3,294 sqft
• 1850 aster drive, Winter Park 32792 Pending $485,000 · 4 bd · 3 ba · 1,656 sqft
• 2625 park place drive, Winter Park 32789 Pending $1,799,000 · 4 bd · 5 ba · 3,460 sqft
• 2560 franklin avenue, Winter Park 32789 Pending $479,000 · 4 bd · 2 ba · 1,514 sqft
• 950 south kentucky avenue, Winter Park 32789 Pending $799,000 · 4 bd · 3 ba · 2,155 sqft
• 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
• 1592 arbor park drive, Winter Park 32789 Pending $700,000 · 4 bd · 3 ba · 2,016 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
• 1800 magnolia avenue, Winter Park 32789 Active Under Contract $950,000 · 4 bd · 3 ba · 2,431 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
• 3114 heartleaf place, Winter Park 32792 Active Under Contract $685,000 · 4 bd · 3 ba · 2,702 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
• 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
• 1420 magnolia avenue, Winter Park 32789 Active Under Contract $1,690,000 · 4 bd · 4 ba · 3,174 sqft
• 2803 banchory road, Winter Park 32792 Active Under Contract $474,000 · 4 bd · 2 ba · 1,596 sqft
• 2831 mulford avenue, Winter Park 32789 Active Under Contract $635,000 · 4 bd · 3 ba · 1,647 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
• 1610 gladiolas drive, Winter Park 32792 Active Under Contract $399,800 · 4 bd · 2 ba · 1,808 sqft
• 4887 north magnolia avenue, Winter Park 32792 Active Under Contract $495,000 · 4 bd · 3 ba · 1,955 sqft
• 1189 lazy hollow place, Winter Park 32792 Active Under Contract $445,000 · 4 bd · 2 ba · 1,525 sqft
• 729 monmouth way, Winter Park 32792 Active Under Contract $799,000 · 4 bd · 3 ba · 2,332 sqft
• 2087 laurelwood way, Winter Park 32792 Active Under Contract $625,000 · 4 bd · 2 ba · 1,920 sqft
• 1908 cyril court, Winter Park 32792 Active Under Contract $639,000 · 4 bd · 3 ba · 2,471 sqft
• 4965 orange avenue, Winter Park 32792 Active Under Contract $370,000 · 4 bd · 2 ba · 1,444 sqft