Homes under $1M in Winter Park, FL
157 for sale · 591 homes listed · Updated September 27, 2026 · Page 2 of 12
- 1000 south semoran boulevard #302, Winter Park 32792 $105,000 · 1 bd · 1 ba · 796 sqft
- 3651 north goldenrod road #c205, Winter Park 32792 $159,900 · 2 bd · 2 ba · 840 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
- 900 carver street, Winter Park 32789 $689,000 · 3 bd · 3 ba · 1,794 sqft
- 7476 woodburn court #38, Winter Park 32792 $170,000 · 2 bd · 3 ba · 1,031 sqft
- 560 ololu drive, Winter Park 32789 $899,000 · 2 bd · 2 ba · 1,086 sqft
- 1871 bryan avenue, Winter Park 32789 $625,000 · 3 bd · 2 ba · 1,232 sqft
- 623 grenadine court #623, Winter Park 32792 $194,900 · 2 bd · 2 ba · 1,037 sqft
- 1652 berkshire avenue, Winter Park 32789 $479,000 · 3 bd · 2 ba · 1,498 sqft
- 2857 clever lane, Winter Park 32792 $399,995 · 3 bd · 3 ba · 1,782 sqft
- 151 north orlando ave ##115, Winter Park 32789 $285,000 · 2 bd · 1 ba · 710 sqft
- 447 north phelps avenue, Winter Park 32789 $960,000 · 2 bd · 1 ba · 1,290 sqft
- 1695 lee road #a101, Winter Park 32789 $154,900 · 3 bd · 2 ba · 1,149 sqft
- 151 north orlando avenue #242, Winter Park 32789 $269,000 · 2 bd · 1 ba · 710 sqft
- 913 moss lane, Winter Park 32789 $950,000 · 3 bd · 2 ba · 1,887 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
- 1386 clematis lane, Winter Park 32792 $427,000 · 4 bd · 3 ba · 1,714 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
- 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
- 2463 grand teton circle #2463, Winter Park 32792 $249,000 · 3 bd · 3 ba · 1,720 sqft
- 7302 swallow run #7302, Winter Park 32792 $134,900 · 2 bd · 2 ba · 756 sqft
- 860 north denning drive, Winter Park 32789 $674,900 · 3 bd · 3 ba · 1,411 sqft
- 3006 northwood boulevard, Winter Park 32789 $950,000 · 4 bd · 3 ba · 2,075 sqft
- 3071 george mason avenue #5, Winter Park 32792 $89,900 · 1 ba · 549 sqft
- 2275 island run, Winter Park 32792 $299,990 · 3 bd · 2 ba · 1,467 sqft
- 274 north ranger boulevard, Winter Park 32792 $669,900 · 3 bd · 2 ba · 1,420 sqft
- 2410 sherbrooke road, Winter Park 32792 $789,000 · 4 bd · 3 ba · 2,141 sqft
- 2500 lee road #143, Winter Park 32789 $130,000 · 1 bd · 1 ba · 645 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
- 2112 eastbrook boulevard, Winter Park 32792 $423,000 · 3 bd · 2 ba · 1,470 sqft
- 2302 barbados drive, Winter Park 32792 $295,000 · 2 bd · 2 ba · 1,544 sqft
- 2260 coldstream drive, Winter Park 32792 $699,000 · 4 bd · 2 ba · 1,509 sqft
- 1256 melissa court, Winter Park 32789 $660,000 · 3 bd · 3 ba · 1,690 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
- 311 east morse boulevard #4-5, Winter Park 32789 $975,000 · 2 bd · 2 ba · 1,763 sqft
- 2572 fifeshire drive, Winter Park 32792 $925,000 · 4 bd · 3 ba · 2,578 sqft
- 2017 canny cove, Winter Park 32792 $389,900 · 3 bd · 3 ba · 1,907 sqft
- 5588 garden grove circle, Winter Park 32792 $395,000 · 3 bd · 2 ba · 1,310 sqft
- 602 trinidad court #602, Winter Park 32792 $227,000 · 2 bd · 2 ba · 1,120 sqft