Homes under $400K in Winter Park, FL
93 for sale · 275 homes listed · Updated November 9, 2026 · Page 1 of 6
- 7429 Daniel Webster Drive 14 #C, Winter Park 32792 $133,000 · 2 bd · 2 ba · 1,036 sqft
- 4027 Northlight Drive Unit 4, Winter Park 34112 $259,900 · 2 bd · 2 ba · 1,234 sqft
- 1995 Canny Cove, Winter Park 32792 $399,000 · 3 bd · 3 ba · 1,907 sqft
- 500 North Pennsylvania Avenue #G, Winter Park 32789 $349,500 · 2 bd · 1 ba · 709 sqft
- 2712 Tortoise Cove, Winter Park 32792 $230,000 · 2 bd · 1 ba · 924 sqft
- 1401 Aster Court, Winter Park 32792 $399,999 · 4 bd · 2 ba · 1,653 sqft
- 151 North Orlando Avenue #118, Winter Park 32789 $299,999 · 2 bd · 1 ba · 710 sqft
- 2477 Tahoe Circle #2477, Winter Park 32792 $247,000 · 2 bd · 2 ba · 1,316 sqft
- 7488 Whisperwood Drive #28, Winter Park 32792 $210,000 · 2 bd · 3 ba · 1,578 sqft
- 5184 Lazy Oaks Drive, Winter Park 32792 $268,000 · 2 bd · 2 ba · 1,008 sqft
- 1605 Puritan Avenue, Winter Park 32792 $374,000 · 3 bd · 2 ba · 1,285 sqft
- 7605 Aloma Pines Court, Winter Park 32792 $349,000 · 3 bd · 3 ba · 1,872 sqft
- 193 Lewfield Circle, Winter Park 32792 $246,400 · 2 bd · 3 ba · 1,300 sqft
- 285 Lewfield Circle #285, Winter Park 32792 $147,000 · 1 bd · 1 ba · 678 sqft
- 2918 Antique Oaks Circle #25, Winter Park 32792 $189,000 · 2 bd · 2 ba · 1,018 sqft
- 311 Scottsdale Square #311, Winter Park 32792 $109,000 · 1 bd · 1 ba · 785 sqft
- 7530 Cranes Creek Court, Winter Park 32792 $306,900 · 3 bd · 3 ba · 1,545 sqft
- 2450 Grand Teton Circle #2450, Winter Park 32792 $250,000 · 3 bd · 2 ba · 1,311 sqft
- 2033 Canny Cove, Winter Park 32792 $389,000 · 3 bd · 3 ba · 1,907 sqft
- 5108 Lazy Oaks Drive #5108, Winter Park 32792 $255,000 · 2 bd · 2 ba · 1,008 sqft
- 283 Sandlewood Trail #3, Winter Park 32789 $279,000 · 2 bd · 3 ba · 960 sqft
- 7384 Grand Avenue, Winter Park 32792 $385,000 · 3 bd · 2 ba · 1,162 sqft
- 7413 Belle River Court #3, Winter Park 32792 $214,900 · 3 bd · 3 ba · 1,151 sqft
- 1250 South Denning Drive Unit 233, Winter Park 32789 $242,500 · 2 bd · 2 ba · 913 sqft
- 1955 Eland Avenue, Winter Park 32789 $394,900 · 3 bd · 2 ba · 1,494 sqft
- 1000 South Semoran Boulevard #302, Winter Park 32792 $97,000 · 1 bd · 1 ba · 796 sqft
- 3562 Bougainvillea Drive, Winter Park 32792 $334,000 · 3 bd · 2 ba · 1,149 sqft
- 7476 Woodburn Court #38, Winter Park 32792 $170,000 · 2 bd · 3 ba · 1,031 sqft
- 623 Grenadine Court #623, Winter Park 32792 $194,900 · 2 bd · 2 ba · 1,037 sqft
- 2857 Clever Lane, Winter Park 32792 $394,500 · 3 bd · 3 ba · 1,782 sqft
- 151 North Orlando Ave ##115, Winter Park 32789 $285,000 · 2 bd · 1 ba · 710 sqft
- 151 North Orlando Avenue #242, Winter Park 32789 $269,000 · 2 bd · 1 ba · 710 sqft
- 2383 Sun Valley Circle #2383, Winter Park 32792 $234,900 · 2 bd · 2 ba · 1,295 sqft
- 1695 Lee Road #D211, Winter Park 32789 $99,900 · 2 bd · 1 ba · 881 sqft
- 311 East Morse Boulevard #7-11, Winter Park 32789 $279,000 · 1 bd · 1 ba · 570 sqft
- 5080 Seminole Avenue, Winter Park 32792 $299,900 · 3 bd · 2 ba · 1,078 sqft
- 2463 Grand Teton Circle #2463, Winter Park 32792 $249,000 · 3 bd · 3 ba · 1,720 sqft
- 3071 George Mason Avenue #5, Winter Park 32792 $89,900 · 1 ba · 549 sqft
- 2275 Island Run, Winter Park 32792 $279,999 · 3 bd · 2 ba · 1,467 sqft
- 7327 Forest Hill Court #223, Winter Park 32792 $175,000 · 2 bd · 3 ba · 1,031 sqft
- 1306 South Pennsylvania Avenue #5, Winter Park 32789 $347,500 · 2 bd · 1 ba · 830 sqft
- 7348 Grand Avenue, Winter Park 32792 $255,000 · 3 bd · 2 ba · 1,509 sqft
- 7560 Aloma Pines Court, Winter Park 32792 $325,000 · 3 bd · 3 ba · 1,866 sqft
- 7450 Wynnewood Square #189, Winter Park 32792 $170,000 · 2 bd · 3 ba · 1,031 sqft
- 3370 Cedar Springs Place #156, Winter Park 32792 $179,990 · 2 bd · 3 ba · 1,031 sqft
- 192 Balfour Drive #2, Winter Park 32792 $319,000 · 2 bd · 2 ba · 1,287 sqft
- 1840 Aster Drive, Winter Park 32792 $374,900 · 3 bd · 2 ba · 1,666 sqft
- 2305 Sun Valley Circle, Winter Park 32792 $279,900 · 2 bd · 2 ba · 1,295 sqft
- 1250 South Denning Drive #127, Winter Park 32789 $245,000 · 2 bd · 2 ba · 908 sqft
- 2475 Tahoe Circle, Winter Park 32792 $268,000 · 2 bd · 2 ba · 1,295 sqft