Single Family Homes in Winter Park, FL
168 for sale · 599 homes listed · Updated September 27, 2026 · Page 3 of 12
- 857 brock street, Winter Park 32789 $4,650,000 · 5 bd · 6 ba · 4,827 sqft
- 1773 walnut avenue, Winter Park 32789 $2,725,000 · 5 bd · 5 ba · 3,784 sqft
- 341 east reading way, Winter Park 32789 $1,525,000 · 4 bd · 4 ba · 3,723 sqft
- 1754 taylor avenue, Winter Park 32789 $2,569,999 · 5 bd · 5 ba · 3,670 sqft
- 525 south lakemont avenue, Winter Park 32792 $1,999,990 · 4 bd · 4 ba · 3,330 sqft
- 751 pansy avenue, Winter Park 32789 $1,950,000 · 3 bd · 4 ba · 2,703 sqft
- 443 broadview avenue, Winter Park 32789 $1,095,000 · 4 bd · 3 ba · 2,803 sqft
- 5588 garden grove circle, Winter Park 32792 $395,000 · 3 bd · 2 ba · 1,310 sqft
- 1570 palmer avenue, Winter Park 32789 $1,595,000 · 4 bd · 4 ba · 3,048 sqft
- 1627 mizell avenue, Winter Park 32789 $3,300,000 · 5 bd · 6 ba · 3,421 sqft
- 541 west canton avenue, Winter Park 32789 $2,495,000 · 4 bd · 4 ba · 3,553 sqft
- 1836 whitehall drive, Winter Park 32789 $2,995,000 · 5 bd · 7 ba · 4,168 sqft
- 3209 heartwood avenue, Winter Park 32792 $449,900 · 4 bd · 2 ba · 1,627 sqft
- 2007 cornell avenue, Winter Park 32789 $449,000 · 3 bd · 2 ba · 1,154 sqft
- 7525 lodge pole trail, Winter Park 32792 $575,000 · 4 bd · 2 ba · 1,936 sqft
- 338 blue heron drive, Winter Park 32789 $836,000 · 3 bd · 3 ba · 2,017 sqft
- 1821 englewood road, Winter Park 32789 $3,075,000 · 5 bd · 6 ba · 3,863 sqft
- 2228 azalea place, Winter Park 32789 $5,600,000 · 5 bd · 6 ba · 5,152 sqft
- 1849 viburnum lane, Winter Park 32792 $389,900 · 4 bd · 2 ba · 1,627 sqft
- 1526 miller avenue, Winter Park 32789 $1,574,900 · 5 bd · 5 ba · 3,252 sqft
- 618 blairshire circle, Winter Park 32792 $895,000 · 4 bd · 3 ba · 1,876 sqft
- 446 melrose avenue, Winter Park 32789 $1,525,000 · 4 bd · 2 ba · 2,640 sqft
- 698 north new york avenue, Winter Park 32789 $6,195,000 · 5 bd · 6 ba · 5,096 sqft
- 532 langholm drive, Winter Park 32789 $2,990,000 · 5 bd · 5 ba · 4,050 sqft
- 2614 parkland drive, Winter Park 32789 $1,890,000 · 4 bd · 4 ba · 3,307 sqft
- 2122 ridge drive, Winter Park 32792 $360,000 · 4 bd · 3 ba · 1,664 sqft
- 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
- 2345 brookshire avenue, Winter Park 32792 $850,000 · 3 bd · 3 ba · 2,488 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
- 259 orange terrace drive, Winter Park 32789 $449,900 · 3 bd · 2 ba · 1,248 sqft
- 914 enclave place, Winter Park 32792 $2,070,000 · 5 bd · 5 ba · 3,617 sqft
- 946 enclave place, Winter Park 32792 $2,375,000 · 5 bd · 5 ba · 3,989 sqft
- 930 enclave place, Winter Park 32792 $2,275,000 · 5 bd · 5 ba · 3,813 sqft
- 938 enclave place, Winter Park 32792 $2,300,000 · 5 bd · 5 ba · 3,865 sqft
- 720 pansy avenue, Winter Park 32789 $1,295,000 · 3 bd · 4 ba · 2,191 sqft
- 2215 woodcrest drive, Winter Park 32792 $675,000 · 4 bd · 2 ba · 1,688 sqft
- 4870 seminole avenue, Winter Park 32792 $380,000 · 3 bd · 2 ba · 1,277 sqft
- 641 northwood circle, Winter Park 32789 $1,499,000 · 3 bd · 5 ba · 2,756 sqft
- 5303 pine lily circle, Winter Park 32792 $659,000 · 3 bd · 2 ba · 2,265 sqft
- 1761 legion drive, Winter Park 32789 $3,265,000 · 5 bd · 6 ba · 4,949 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
- 950 hanover avenue, Winter Park 32789 $439,000 · 3 bd · 2 ba · 1,606 sqft
- 2818 ambergate road, Winter Park 32792 $429,900 · 3 bd · 2 ba · 1,398 sqft
- 739 roughbeard road, Winter Park 32792 $780,000 · 5 bd · 3 ba · 2,194 sqft
- 1660 orange avenue, Winter Park 32789 $479,900 · 3 bd · 2 ba · 1,614 sqft