Single Family Homes in Winter Park, FL
168 for sale · 599 homes listed · Updated September 27, 2026 · Page 1 of 12
- 7641 village green drive, Winter Park 32792 $539,000 · 3 bd · 3 ba · 1,602 sqft
- 1591 cardinal court, Winter Park 32789 $2,995,000 · 5 bd · 3 ba · 3,523 sqft
- 1164 dodd road, Winter Park 32792 $775,000 · 5 bd · 4 ba · 2,840 sqft
- 5409 albert drive, Winter Park 32792 $410,000 · 3 bd · 2 ba · 1,483 sqft
- 1842 puritan avenue, Winter Park 32792 $419,000 · 4 bd · 2 ba · 1,836 sqft
- 1535 lawndale circle, Winter Park 32792 $420,000 · 3 bd · 2 ba · 1,676 sqft
- 231 chelton circle, Winter Park 32789 $4,700,000 · 4 bd · 7 ba · 5,550 sqft
- 1864 grinnell terrace, Winter Park 32789 $1,599,000 · 5 bd · 4 ba · 3,028 sqft
- 2240 venetian way, Winter Park 32789 $3,500,000 · 4 bd · 4 ba · 4,036 sqft
- 2715 prince john road, Winter Park 32792 $494,900 · 3 bd · 2 ba · 1,565 sqft
- 2041 jewell avenue, Winter Park 32789 $439,900 · 3 bd · 1 ba · 1,508 sqft
- 240 killarney drive, Winter Park 32789 $1,275,000 · 3 bd · 3 ba · 1,329 sqft
- 1113 via del mar, Winter Park 32789 $1,595,000 · 3 bd · 2 ba · 2,012 sqft
- 1840 anzle avenue, Winter Park 32789 $1,750,000 · 4 bd · 3 ba · 2,350 sqft
- 281 brewer avenue, Winter Park 32789 $1,800,000 · 5 bd · 5 ba · 4,029 sqft
- 5316 halyard court, Winter Park 32792 $495,000 · 3 bd · 2 ba · 1,380 sqft
- 1870 staunton avenue, Winter Park 32789 $1,250,000 · 4 bd · 4 ba · 2,525 sqft
- 1562 arbor park drive, Winter Park 32789 $775,000 · 4 bd · 3 ba · 1,899 sqft
- 2308 mulbry drive, Winter Park 32789 $1,699,000 · 4 bd · 4 ba · 2,530 sqft
- 1564 lawndale circle, Winter Park 32792 $450,000 · 4 bd · 3 ba · 1,980 sqft
- 1605 puritan avenue, Winter Park 32792 $379,000 · 3 bd · 2 ba · 1,285 sqft
- 3740 hawthorne lane, Winter Park 32792 $435,000 · 3 bd · 2 ba · 1,645 sqft
- 1319 bessmor road, Winter Park 32789 $589,000 · 3 bd · 2 ba · 1,126 sqft
- 2286 marsh sedge lane, Winter Park 32792 $770,000 · 4 bd · 3 ba · 2,192 sqft
- 437 north capen avenue, Winter Park 32789 $849,000 · 3 bd · 3 ba · 1,904 sqft
- 230 strathy lane, Winter Park 32792 $499,000 · 2 bd · 1 ba · 920 sqft
- 1131 wildmeadow run, Winter Park 32792 $825,000 · 4 bd · 4 ba · 2,589 sqft
- 276 detmar drive, Winter Park 32789 $3,600,000 · 4 bd · 5 ba · 4,202 sqft
- 1927 eland avenue, Winter Park 32789 $820,000 · 5 bd · 3 ba · 2,242 sqft
- 1420 aloma avenue, Winter Park 32789 $1,949,500 · 3 bd · 4 ba · 2,422 sqft
- 1441 cardinal court, Winter Park 32789 $3,995,000 · 4 bd · 6 ba · 4,066 sqft
- 715 south ranger boulevard, Winter Park 32792 $695,000 · 4 bd · 3 ba · 2,312 sqft
- 1122 wildmeadow run, Winter Park 32792 $665,000 · 4 bd · 3 ba · 1,770 sqft
- 3440 allston lane, Winter Park 32792 $405,000 · 3 bd · 3 ba · 1,533 sqft
- 2418 euston road, Winter Park 32789 $624,444 · 3 bd · 3 ba · 2,228 sqft
- 1003 lake bell drive, Winter Park 32789 $549,900 · 3 bd · 2 ba · 1,837 sqft
- 1840 laurel road, Winter Park 32789 $2,299,000 · 5 bd · 5 ba · 2,868 sqft
- 7384 grand avenue, Winter Park 32792 $425,000 · 3 bd · 2 ba · 1,162 sqft
- 2667 cochise trail, Winter Park 32789 $985,000 · 4 bd · 3 ba · 2,868 sqft
- 981 aragon avenue, Winter Park 32789 $494,999 · 2 bd · 1 ba · 857 sqft
- 1448 lake florence way, Winter Park 32792 $1,049,900 · 5 bd · 5 ba · 3,652 sqft
- 1955 eland avenue, Winter Park 32789 $410,000 · 3 bd · 2 ba · 1,494 sqft
- 160 west rockwood way, Winter Park 32789 $3,395,000 · 5 bd · 6 ba · 4,015 sqft
- 2758 banchory road, Winter Park 32792 $639,000 · 3 bd · 3 ba · 1,539 sqft
- 1404 border drive, Winter Park 32789 $1,075,000 · 4 bd · 4 ba · 2,469 sqft
- 1903 north park avenue, Winter Park 32789 $1,649,000 · 4 bd · 4 ba · 2,807 sqft
- 2703 tierra circle, Winter Park 32792 $464,000 · 3 bd · 2 ba · 1,737 sqft
- 2641 carvell court, Winter Park 32792 $550,000 · 4 bd · 2 ba · 2,126 sqft
- 3562 bougainvillea drive, Winter Park 32792 $334,000 · 3 bd · 2 ba · 1,149 sqft
- 2824 prince john road, Winter Park 32792 $475,000 · 2 bd · 2 ba · 1,438 sqft