Homes under $1M in Winter Park, FL
199 homes for sale · Updated August 12, 2026 · Page 2 of 4
- 1741 westchester avenue, Winter Park 32789 $569,900 · 3 bd · 2 ba · 1,434 sqft
- 2317 sun valley circle 2317, Winter Park 32792 $267,000 · 2 bd · 2 ba · 1,295 sqft
- 2383 sun valley circle 2383, Winter Park 32792 $245,000 · 2 bd · 2 ba · 1,295 sqft
- 1319 bessmor road, Winter Park 32789 $589,000 · 3 bd · 2 ba · 1,126 sqft
- 7429 daniel webster drive 14 #c, Winter Park 32792 $133,000 · 2 bd · 2 ba · 1,036 sqft
- 1287 verdant glade place, Winter Park 32792 $775,000 · 4 bd · 4 ba · 3,020 sqft
- 3440 allston lane, Winter Park 32792 $405,000 · 3 bd · 3 ba · 1,533 sqft
- 1611 chestnut avenue, Winter Park 32789 $995,000 · 4 bd · 4 ba · 2,916 sqft
- 3374 hamlet loop, Winter Park 32792 $360,000 · 3 bd · 3 ba · 1,397 sqft
- 525 ololu drive, Winter Park 32789 $495,900 · 3 bd · 3 ba · 1,786 sqft
- 1695 lee road b210, Winter Park 32789 $89,000 · 1 bd · 1 ba · 638 sqft
- 1438 tierra circle, Winter Park 32792 $514,900 · 3 bd · 2 ba · 1,627 sqft
- 7327 forest hill court 223, Winter Park 32792 $175,000 · 2 bd · 3 ba · 1,031 sqft
- 5806 marble court, Winter Park 32792 $289,000 · 2 bd · 2 ba · 1,140 sqft
- 2500 lee road 232, Winter Park 32789 $149,000 · 1 bd · 1 ba · 645 sqft
- 440 cambridge boulevard, Winter Park 32789 $369,900 · 2 bd · 1 ba · 988 sqft
- 262 lewfield circle 262, Winter Park 32792 $149,500 · 1 bd · 1 ba · 678 sqft
- 3243 forest oaks court 117, Winter Park 32792 $172,000 · 2 bd · 2 ba · 990 sqft
- 2215 woodcrest drive, Winter Park 32792 $695,000 · 4 bd · 2 ba · 1,688 sqft
- 1092 eastbrook boulevard, Winter Park 32792 $399,000 · 3 bd · 2 ba · 1,122 sqft
- 1995 canny cove, Winter Park 32792 $425,000 · 3 bd · 3 ba · 1,907 sqft
- 1500 gay road 17d, Winter Park 32789 $239,500 · 2 bd · 2 ba · 1,026 sqft
- 1707 harmon avenue, Winter Park 32789 $599,000 · 3 bd · 2 ba · 1,669 sqft
- 2503 tahoe circle 2503, Winter Park 32792 $225,000 · 2 bd · 2 ba · 1,173 sqft
- 2512 eastbrook boulevard, Winter Park 32792 $390,000 · 4 bd · 2 ba · 1,607 sqft
- 2923 antique oaks circle 34, Winter Park 32792 $180,000 · 2 bd · 2 ba · 1,105 sqft
- 269 east canton avenue 269, Winter Park 32789 $989,500 · 1 bd · 2 ba · 1,109 sqft
- 333 cornwall road, Winter Park 32792 $549,900 · 4 bd · 2 ba · 1,660 sqft
- 300 carolina avenue 402c, Winter Park 32789 $750,000 · 3 bd · 2 ba · 1,350 sqft
- 616 brechin drive, Winter Park 32792 $999,000 · 4 bd · 5 ba · 2,638 sqft
- 1741 mizell avenue, Winter Park 32789 $998,000 · 3 bd · 2 ba · 2,015 sqft
- 700 melrose avenue j24, Winter Park 32789 $380,000 · 1 bd · 1 ba · 987 sqft
- 1009 lake bell drive, Winter Park 32789 $650,000 · 3 bd · 2 ba · 1,467 sqft
- 1540 florentino lane, Winter Park 32792 $315,000 · 3 bd · 3 ba · 1,682 sqft
- 7522 aloma pines court, Winter Park 32792 $375,000 · 3 bd · 3 ba · 1,872 sqft
- 193 lewfield circle, Winter Park 32792 $248,900 · 2 bd · 3 ba · 1,300 sqft
- 316 beckett court, Winter Park 32792 $450,000 · 4 bd · 2 ba · 1,651 sqft
- 1946 strathaven road, Winter Park 32792 $599,000 · 4 bd · 3 ba · 2,102 sqft
- 2418 euston road, Winter Park 32789 $657,777 · 3 bd · 3 ba · 2,228 sqft
- 200 saint andrews boulevard 704, Winter Park 32792 $164,999 · 1 bd · 1 ba · 793 sqft
- 1320 gladiolas drive, Winter Park 32792 $474,000 · 4 bd · 2 ba · 1,624 sqft
- 338 blue heron drive, Winter Park 32789 $840,000 · 3 bd · 3 ba · 2,017 sqft
- 1840 aster drive, Winter Park 32792 $414,900 · 3 bd · 2 ba · 1,667 sqft
- 860 north denning drive, Winter Park 32789 $699,900 · 3 bd · 3 ba · 1,411 sqft
- 2006 cornell avenue, Winter Park 32789 $328,000 · 2 bd · 1 ba · 797 sqft
- 715 south ranger boulevard, Winter Park 32792 $695,000 · 4 bd · 3 ba · 2,312 sqft
- 2054 eastbrook boulevard, Winter Park 32792 $500,000 · 4 bd · 3 ba · 2,031 sqft
- 1250 formosa avenue, Winter Park 32789 $550,000 · 3 bd · 4 ba · 1,937 sqft
- 5503 albert drive, Winter Park 32792 $399,990 · 3 bd · 2 ba · 1,366 sqft
- 840 west canton avenue, Winter Park 32789 $649,900 · 3 bd · 2 ba · 1,370 sqft