4 Bedroom Homes in Winter Park, FL

67 for sale · 252 homes listed · Updated September 27, 2026 · Page 5 of 6

• 1271 palmer avenue, Winter Park 32789 Off market since Sep 2026 $2,275,000 · 4 bd · 5 ba · 2,835 sqft
• 1546 miller avenue, Winter Park 32789 Off market since Sep 2026 $1,419,900 · 4 bd · 4 ba · 2,984 sqft
• 2525 lafayette avenue, Winter Park 32789 Off market since Sep 2026 $1,749,000 · 4 bd · 4 ba · 2,715 sqft
• 525 south lakemont avenue, Winter Park 32792 Off market since Sep 2026 $1,999,990 · 4 bd · 4 ba · 3,330 sqft
• 2251 nairn drive, Winter Park 32792 Off market since Aug 2026 $625,000 · 4 bd · 3 ba · 1,978 sqft
• 361 east kings way, Winter Park 32789 Off market since Sep 2026 $3,199,000 · 4 bd · 5 ba · 3,737 sqft
• 2667 cochise trail, Winter Park 32789 Off market since Sep 2026 $985,000 · 4 bd · 3 ba · 2,868 sqft
• 1122 wildmeadow run, Winter Park 32792 Off market since Sep 2026 $665,000 · 4 bd · 3 ba · 1,770 sqft
• 1840 bryan avenue, Winter Park 32789 Off market since Sep 2026 $1,725,000 · 4 bd · 4 ba · 3,727 sqft
• 2308 mulbry drive, Winter Park 32789 Off market since Sep 2026 $1,699,000 · 4 bd · 4 ba · 2,530 sqft
• 2343 versailles avenue, Winter Park 32789 Off market since Sep 2026 $1,750,000 · 4 bd · 4 ba · 3,307 sqft
• 2627 ambergate road, Winter Park 32792 Off market since Sep 2026 $575,000 · 4 bd · 3 ba · 1,745 sqft
• 2286 marsh sedge lane, Winter Park 32792 Off market since Sep 2026 $770,000 · 4 bd · 3 ba · 2,192 sqft
• 2641 carvell court, Winter Park 32792 Off market since Sep 2026 $550,000 · 4 bd · 2 ba · 2,126 sqft
• 1842 puritan avenue, Winter Park 32792 Off market since Sep 2026 $419,000 · 4 bd · 2 ba · 1,836 sqft
• 943 fairway drive, Winter Park 32792 Off market since Sep 2026 $650,000 · 4 bd · 3 ba · 2,067 sqft
• 7525 lodge pole trail, Winter Park 32792 Off market since Sep 2026 $575,000 · 4 bd · 2 ba · 1,936 sqft
• 1016 aragon avenue, Winter Park 32789 Off market since Sep 2026 $660,000 · 4 bd · 4 ba · 1,840 sqft
• 276 detmar drive, Winter Park 32789 Off market since Sep 2026 $3,600,000 · 4 bd · 5 ba · 4,202 sqft
• 1550 palm avenue, Winter Park 32789 Off market since Sep 2026 $1,829,000 · 4 bd · 4 ba · 2,706 sqft
• 2430 chantilly avenue, Winter Park 32789 Off market since Sep 2026 $1,598,000 · 4 bd · 4 ba · 2,916 sqft
• 471 holt avenue, Winter Park 32789 Off market since Sep 2026 $975,000 · 4 bd · 3 ba · 2,528 sqft
• 443 broadview avenue, Winter Park 32789 Off market since Sep 2026 $1,095,000 · 4 bd · 3 ba · 2,803 sqft
• 702 via bella, Winter Park 32789 Off market since Sep 2026 $4,400,000 · 4 bd · 6 ba · 3,720 sqft
• 2211 king richards court, Winter Park 32792 Off market since Sep 2026 $529,000 · 4 bd · 2 ba · 1,845 sqft
• 1702 arbor park drive, Winter Park 32789 Off market since Sep 2026 $1,900,000 · 4 bd · 4 ba · 2,950 sqft
• 4039 cool water court, Winter Park 32792 Off market since Sep 2026 $739,777 · 4 bd · 2 ba · 2,267 sqft
• 3020 nicholson drive, Winter Park 32792 Off market since Sep 2026 $495,000 · 4 bd · 2 ba · 1,756 sqft
• 1320 orchid avenue, Winter Park 32789 Off market since Sep 2026 $1,350,000 · 4 bd · 4 ba · 2,998 sqft
• 2122 ridge drive, Winter Park 32792 Off market since Sep 2026 $360,000 · 4 bd · 3 ba · 1,664 sqft
• 2661 via tuscany, Winter Park 32789 Off market since Sep 2026 $5,999,990 · 4 bd · 5 ba · 3,880 sqft
• 2260 coldstream drive, Winter Park 32792 Off market since Sep 2026 $699,000 · 4 bd · 2 ba · 1,509 sqft
• 2622 lake howell lane, Winter Park 32792 Off market since Sep 2026 $3,750,000 · 4 bd · 3 ba · 3,377 sqft
• 952 moss lane, Winter Park 32789 Off market since Sep 2026 $1,319,950 · 4 bd · 5 ba · 3,474 sqft
• 2410 sherbrooke road, Winter Park 32792 Off market since Sep 2026 $789,000 · 4 bd · 3 ba · 2,141 sqft
• 540 north pennsylvania avenue, Winter Park 32789 Off market since Sep 2026 $3,950,000 · 4 bd · 2 ba · 1,652 sqft
• 2301 conifer avenue, Winter Park 32792 Off market since Sep 2026 $450,000 · 4 bd · 2 ba · 2,189 sqft
• 618 blairshire circle, Winter Park 32792 Off market since Sep 2026 $895,000 · 4 bd · 3 ba · 1,876 sqft
• 1271 palmer avenue, Winter Park 32789 Off market since Sep 2026 $2,195,000 · 4 bd · 5 ba · 2,850 sqft
• 2417 chantilly avenue, Winter Park 32789 Off market since Sep 2026 $1,579,000 · 4 bd · 4 ba · 2,718 sqft
• 1386 clematis lane, Winter Park 32792 Off market since Sep 2026 $427,000 · 4 bd · 3 ba · 1,714 sqft
• 2215 woodcrest drive, Winter Park 32792 Off market since Sep 2026 $675,000 · 4 bd · 2 ba · 1,688 sqft
• 2572 fifeshire drive, Winter Park 32792 Off market since Sep 2026 $925,000 · 4 bd · 3 ba · 2,578 sqft
• 1803 barker drive, Winter Park 32789 Off market since Sep 2026 $2,190,000 · 4 bd · 3 ba · 3,463 sqft
• 1517 harmon avenue, Winter Park 32789 Off market since Sep 2026 $1,095,000 · 4 bd · 4 ba · 2,135 sqft
• 3484 seagrape drive, Winter Park 32792 Off market since Sep 2026 $299,900 · 4 bd · 2 ba · 1,227 sqft
• 1742 temple drive, Winter Park 32789 Off market since Sep 2026 $3,695,999 · 4 bd · 5 ba · 3,658 sqft
• 4260 bear gully road, Winter Park 32792 Off market since Sep 2026 $599,000 · 4 bd · 5 ba · 2,322 sqft
• 533 country club drive, Winter Park 32789 Off market since Sep 2026 $1,599,000 · 4 bd · 4 ba · 2,942 sqft
• 2614 parkland drive, Winter Park 32789 Off market since Sep 2026 $1,890,000 · 4 bd · 4 ba · 3,307 sqft