4 Bedroom Homes in Winter Park, FL

67 for sale · 252 homes listed · Updated September 27, 2026 · Page 4 of 6

1441 cardinal court, Winter Park 32789 Off market since Sep 2026 $3,995,000 · 4 bd · 6 ba · 4,066 sqft
1398 grove terrace, Winter Park 32789 Off market since Sep 2026 $1,995,000 · 4 bd · 4 ba · 3,450 sqft
814 densmore drive, Winter Park 32792 Off market since Sep 2026 $425,000 · 4 bd · 2 ba · 1,610 sqft
2111 mallard circle, Winter Park 32789 Off market since Jul 2026 $1,199,000 · 4 bd · 3 ba · 2,667 sqft
363 north phelps avenue, Winter Park 32789 Off market since Jul 2026 $1,249,000 · 4 bd · 3 ba · 2,871 sqft
1287 verdant glade place, Winter Park 32792 Off market since Aug 2026 $775,000 · 4 bd · 4 ba · 3,020 sqft
420 ohio street, Winter Park 32789 Off market since Jul 2026 $1,275,000 · 4 bd · 4 ba · 2,900 sqft
1611 chestnut avenue, Winter Park 32789 Off market since Sep 2026 $995,000 · 4 bd · 4 ba · 2,916 sqft
446 melrose avenue, Winter Park 32789 Off market since Sep 2026 $1,525,000 · 4 bd · 2 ba · 2,640 sqft
2232 banchory road, Winter Park 32792 Off market since Jul 2026 $1,115,000 · 4 bd · 3 ba · 2,597 sqft
1606 miller avenue, Winter Park 32789 Off market since Sep 2026 $1,249,900 · 4 bd · 4 ba · 2,936 sqft
2430 chantilly avenue, Winter Park 32789 Off market since Sep 2026 $1,599,000 · 4 bd · 4 ba · 2,916 sqft
2215 woodcrest drive, Winter Park 32792 Off market since Aug 2026 $695,000 · 4 bd · 2 ba · 1,688 sqft
2333 westminster court, Winter Park 32789 Off market since Jul 2026 $689,000 · 4 bd · 2 ba · 1,877 sqft
2512 eastbrook boulevard, Winter Park 32792 Off market since Sep 2026 $390,000 · 4 bd · 2 ba · 1,607 sqft
333 cornwall road, Winter Park 32792 Off market since Sep 2026 $549,900 · 4 bd · 2 ba · 1,660 sqft
616 brechin drive, Winter Park 32792 Off market since Sep 2026 $999,000 · 4 bd · 5 ba · 2,638 sqft
316 beckett court, Winter Park 32792 Off market since Sep 2026 $450,000 · 4 bd · 2 ba · 1,651 sqft
1946 strathaven road, Winter Park 32792 Off market since Sep 2026 $599,000 · 4 bd · 3 ba · 2,102 sqft
723 symonds avenue, Winter Park 32789 Off market since Sep 2026 $1,700,000 · 4 bd · 4 ba · 3,065 sqft
1581 magnolia avenue, Winter Park 32789 Off market since Sep 2026 $1,425,000 · 4 bd · 4 ba · 2,756 sqft
1320 gladiolas drive, Winter Park 32792 Off market since Sep 2026 $469,900 · 4 bd · 2 ba · 1,624 sqft
1404 border drive, Winter Park 32789 Off market since Sep 2026 $1,075,000 · 4 bd · 4 ba · 2,469 sqft
715 south ranger boulevard, Winter Park 32792 Off market since Sep 2026 $695,000 · 4 bd · 3 ba · 2,312 sqft
2054 eastbrook boulevard, Winter Park 32792 Off market since Sep 2026 $500,000 · 4 bd · 3 ba · 2,031 sqft
2240 venetian way, Winter Park 32789 Off market since Sep 2026 $3,500,000 · 4 bd · 4 ba · 4,036 sqft
525 south lakemont avenue, Winter Park 32792 Off market since Aug 2026 $2,099,990 · 4 bd · 4 ba · 3,330 sqft
231 chelton circle, Winter Park 32789 Off market since Sep 2026 $4,950,000 · 4 bd · 7 ba · 5,550 sqft
1421 chapman circle, Winter Park 32789 Off market since Sep 2026 $1,377,500 · 4 bd · 4 ba · 3,578 sqft
8433 commander cove, Winter Park 32792 Off market since Sep 2026 $455,000 · 4 bd · 3 ba · 1,903 sqft
1316 blue stem lane, Winter Park 32792 Off market since Sep 2026 $725,000 · 4 bd · 3 ba · 2,196 sqft
2008 houndslake drive, Winter Park 32792 Off market since Sep 2026 $475,000 · 4 bd · 2 ba · 2,250 sqft
313 sylvan drive, Winter Park 32789 Off market since Sep 2026 $5,500,000 · 4 bd · 5 ba · 4,775 sqft
2015 summerfield road, Winter Park 32792 Off market since Sep 2026 $1,262,500 · 4 bd · 4 ba · 3,024 sqft
2344 woodcrest drive, Winter Park 32792 Off market since Jul 2026 $719,900 · 4 bd · 2 ba · 1,764 sqft
1564 lawndale circle, Winter Park 32792 Off market since Sep 2026 $450,000 · 4 bd · 3 ba · 1,980 sqft
4353 steed terrace, Winter Park 32792 Off market since Sep 2026 $599,900 · 4 bd · 2 ba · 2,275 sqft
3006 northwood boulevard, Winter Park 32789 Off market since Sep 2026 $950,000 · 4 bd · 3 ba · 2,075 sqft
341 east reading way, Winter Park 32789 Off market since Sep 2026 $1,525,000 · 4 bd · 4 ba · 3,723 sqft
722 south ranger boulevard, Winter Park 32792 Off market since Sep 2026 $775,000 · 4 bd · 3 ba · 2,164 sqft
708 balmoral road, Winter Park 32789 Off market since Sep 2026 $1,590,000 · 4 bd · 3 ba · 2,786 sqft
436 west swoope avenue, Winter Park 32789 Off market since Sep 2026 $699,000 · 4 bd · 4 ba · 2,602 sqft
885 carnation drive, Winter Park 32792 Off market since Sep 2026 $368,000 · 4 bd · 2 ba · 1,240 sqft
1418 lone feather trail, Winter Park 32792 Off market since Sep 2026 $699,500 · 4 bd · 3 ba · 2,197 sqft
922 north pennsylvania avenue, Winter Park 32789 Off market since Sep 2026 $1,875,000 · 4 bd · 4 ba · 3,440 sqft
250 killarney, Winter Park 32789 Off market since Sep 2026 $1,600,000 · 4 bd · 4 ba · 2,568 sqft
1310 fairview avenue, Winter Park 32789 Off market since Aug 2026 $925,000 · 4 bd · 3 ba · 2,552 sqft
1401 aster court, Winter Park 32792 Off market since Sep 2026 $414,900 · 4 bd · 2 ba · 1,653 sqft
1562 arbor park drive, Winter Park 32789 Off market since Sep 2026 $775,000 · 4 bd · 3 ba · 1,899 sqft
230 killarney drive, Winter Park 32789 Off market since Sep 2026 $1,250,000 · 4 bd · 1 ba · 1,260 sqft