Single Family Homes in Winter Park, FL
168 for sale · 599 homes listed · Updated September 27, 2026 · Page 2 of 12
- 1445 via sangro place, Winter Park 32792 $1,350,000 · 6 bd · 6 ba · 5,021 sqft
- 2622 lake howell lane, Winter Park 32792 $3,750,000 · 4 bd · 3 ba · 3,377 sqft
- 900 carver street, Winter Park 32789 $689,000 · 3 bd · 3 ba · 1,794 sqft
- 560 ololu drive, Winter Park 32789 $899,000 · 2 bd · 2 ba · 1,086 sqft
- 702 via bella, Winter Park 32789 $4,400,000 · 4 bd · 6 ba · 3,720 sqft
- 540 north pennsylvania avenue, Winter Park 32789 $3,950,000 · 4 bd · 2 ba · 1,652 sqft
- 1871 bryan avenue, Winter Park 32789 $625,000 · 3 bd · 2 ba · 1,232 sqft
- 2260 mulbry drive, Winter Park 32789 $1,925,000 · 5 bd · 4 ba · 3,246 sqft
- 1652 berkshire avenue, Winter Park 32789 $479,000 · 3 bd · 2 ba · 1,498 sqft
- 447 north phelps avenue, Winter Park 32789 $960,000 · 2 bd · 1 ba · 1,290 sqft
- 913 moss lane, Winter Park 32789 $950,000 · 3 bd · 2 ba · 1,887 sqft
- 462 west lyman avenue, Winter Park 32789 $1,495,000 · 3 bd · 3 ba · 1,944 sqft
- 825 palmer avenue, Winter Park 32789 $5,195,900 · 5 bd · 7 ba · 5,122 sqft
- 2136 linden road, Winter Park 32792 $365,000 · 3 bd · 2 ba · 1,185 sqft
- 1946 strathaven road, Winter Park 32792 $599,000 · 4 bd · 3 ba · 2,102 sqft
- 1092 eastbrook boulevard, Winter Park 32792 $390,000 · 3 bd · 2 ba · 1,122 sqft
- 901 golfview terrace, Winter Park 32789 $6,995,000 · 5 bd · 6 ba · 5,479 sqft
- 1386 clematis lane, Winter Park 32792 $427,000 · 4 bd · 3 ba · 1,714 sqft
- 1166 palmer avenue, Winter Park 32789 $5,500,000 · 5 bd · 7 ba · 5,181 sqft
- 471 holt avenue, Winter Park 32789 $975,000 · 4 bd · 3 ba · 2,528 sqft
- 4039 cool water court, Winter Park 32792 $739,777 · 4 bd · 2 ba · 2,267 sqft
- 508 brechin drive, Winter Park 32792 $629,000 · 3 bd · 2 ba · 1,783 sqft
- 1418 lone feather trail, Winter Park 32792 $699,500 · 4 bd · 3 ba · 2,197 sqft
- 1803 barker drive, Winter Park 32789 $2,190,000 · 4 bd · 3 ba · 3,463 sqft
- 1521 heron wood place, Winter Park 32792 $829,500 · 4 bd · 2 ba · 3,950 sqft
- 5080 seminole avenue, Winter Park 32792 $299,900 · 3 bd · 2 ba · 1,078 sqft
- 860 north denning drive, Winter Park 32789 $674,900 · 3 bd · 3 ba · 1,411 sqft
- 2207 kindel avenue, Winter Park 32789 $1,600,000 · 3 bd · 3 ba · 2,733 sqft
- 3006 northwood boulevard, Winter Park 32789 $950,000 · 4 bd · 3 ba · 2,075 sqft
- 1517 harmon avenue, Winter Park 32789 $1,095,000 · 4 bd · 4 ba · 2,135 sqft
- 274 north ranger boulevard, Winter Park 32792 $669,900 · 3 bd · 2 ba · 1,420 sqft
- 2702 parkland drive, Winter Park 32789 $1,049,000 · 5 bd · 3 ba · 2,656 sqft
- 1841 lake spier drive, Winter Park 32789 $1,498,000 · 3 bd · 4 ba · 2,467 sqft
- 1473 berkshire avenue, Winter Park 32789 $1,369,000 · 5 bd · 4 ba · 2,446 sqft
- 2227 howard drive, Winter Park 32789 $1,100,000 · 3 bd · 3 ba · 2,196 sqft
- 1260 alabama drive, Winter Park 32789 $6,900,000 · 6 bd · 7 ba · 6,396 sqft
- 2410 sherbrooke road, Winter Park 32792 $789,000 · 4 bd · 3 ba · 2,141 sqft
- 1742 temple drive, Winter Park 32789 $3,695,999 · 4 bd · 5 ba · 3,658 sqft
- 1133 bella lago cove, Winter Park 32792 $1,999,900 · 3 bd · 2 ba · 1,765 sqft
- 2417 chantilly avenue, Winter Park 32789 $1,579,000 · 4 bd · 4 ba · 2,718 sqft
- 1220 howell branch road, Winter Park 32789 $999,500 · 3 bd · 2 ba · 1,487 sqft
- 1850 bryan avenue, Winter Park 32789 $725,000 · 3 bd · 2 ba · 1,563 sqft
- 2343 versailles avenue, Winter Park 32789 $1,750,000 · 4 bd · 4 ba · 3,307 sqft
- 2112 eastbrook boulevard, Winter Park 32792 $423,000 · 3 bd · 2 ba · 1,470 sqft
- 2260 coldstream drive, Winter Park 32792 $699,000 · 4 bd · 2 ba · 1,509 sqft
- 250 west reading way, Winter Park 32789 $4,325,000 · 5 bd · 5 ba · 4,853 sqft
- 4260 bear gully road, Winter Park 32792 $599,000 · 4 bd · 4 ba · 2,322 sqft
- 330 elkhorn court, Winter Park 32792 $544,900 · 3 bd · 2 ba · 1,570 sqft
- 1702 arbor park drive, Winter Park 32789 $1,900,000 · 4 bd · 4 ba · 2,950 sqft
- 2572 fifeshire drive, Winter Park 32792 $925,000 · 4 bd · 3 ba · 2,578 sqft