Homes under $1M in Winter Garden, FL

391 for sale · 1,436 homes listed · Updated September 27, 2026 · Page 20 of 29

• 5545 bowman drive, Winter Garden 34787 Off market since Sep 2026 $430,000 · 2 bd · 3 ba · 1,998 sqft
• 6174 whispering glen, Winter Garden 34787 Off market since Sep 2026 $521,990 · 3 bd · 3 ba · 1,628 sqft
• 11117 bostwick alley, Winter Garden 34787 Off market since Sep 2026 $485,000 · 3 bd · 2 ba · 1,685 sqft
• 10294 merrymeeting bay drive, Winter Garden 34787 Off market since Sep 2026 $449,900 · 3 bd · 2 ba · 1,689 sqft
• 16185 taliesin street, Winter Garden 34787 Off market since Sep 2026 $649,990 · 4 bd · 3 ba · 2,372 sqft
• 14755 masthead landing circle, Winter Garden 34787 Off market since Jul 2026 $549,900 · 4 bd · 2 ba · 2,258 sqft
• 8866 bismarck palm drive, Winter Garden 34787 Off market since Sep 2026 $795,000 · 5 bd · 4 ba · 3,174 sqft
• 14784 field daisy drive, Winter Garden 34787 Off market since Sep 2026 $635,699 · 4 bd · 5 ba · 2,841 sqft
• 14501 grove resort avenue 1535, Winter Garden 34787 Off market since Sep 2026 $410,990 · 3 bd · 2 ba · 1,396 sqft
• 17007 haggerty hollow drive, Winter Garden 34787 Off market since Sep 2026 $491,490 · 3 bd · 3 ba · 1,764 sqft
• 7280 windy willow street, Winter Garden 34787 Off market since Sep 2026 $493,583 · 3 bd · 3 ba · 1,772 sqft
• 13527 daniels landing circle, Winter Garden 34787 Off market since Aug 2026 $335,000 · 3 bd · 3 ba · 1,365 sqft
• 10103 austrina oak loop, Winter Garden 34787 Off market since Sep 2026 $899,900 · 5 bd · 4 ba · 4,305 sqft
• 170 windtree lane, Winter Garden 34787 Off market since Sep 2026 $204,900 · 2 bd · 2 ba · 918 sqft
• 14501 grove resort avenue 1439, Winter Garden 34787 Off market since Sep 2026 $169,900 · 2 bd · 2 ba · 1,265 sqft
• 12597 encore at ovation way, Winter Garden 34787 Off market since Sep 2026 $459,000 · 3 bd · 3 ba · 2,322 sqft
• 15111 driftwood bend street, Winter Garden 34787 Off market since Aug 2026 $618,000 · 4 bd · 4 ba · 2,573 sqft
• 330 southern pecan circle 205, Winter Garden 34787 Off market since Aug 2026 $289,000 · 3 bd · 2 ba · 1,453 sqft
• 46 west vining street, Winter Garden 34787 Off market since Aug 2026 $544,900 · 3 bd · 2 ba · 1,273 sqft
• 17106 beachgrass alley, Winter Garden 34787 Off market since Sep 2026 $799,990 · 3 bd · 3 ba · 1,983 sqft
• 1692 highbanks circle, Winter Garden 34787 Off market since Sep 2026 $729,900 · 4 bd · 4 ba · 2,848 sqft
• 14501 grove resort avenue 3211, Winter Garden 34787 Off market since Sep 2026 $271,000 · 3 bd · 2 ba · 1,396 sqft
• 10264 love story street, Winter Garden 34787 Off market since Sep 2026 $875,000 · 5 bd · 3 ba · 3,295 sqft
• 4918 wildwood pointe road, Winter Garden 34787 Off market since Sep 2026 $650,000 · 5 bd · 4 ba · 2,868 sqft
• 14246 creekbed circle, Winter Garden 34787 Off market since Sep 2026 $640,000 · 4 bd · 3 ba · 2,418 sqft
• 15625 boggy oak circle 108b, Winter Garden 34787 Off market since Sep 2026 $335,000 · 3 bd · 3 ba · 1,419 sqft
• 15568 blackbead street, Winter Garden 34787 Sold on Jul 17, 2026 $435,000 · 4 bd · 3 ba · 1,861 sqft
• 17422 honeybell tangelo court, Winter Garden 34787 Off market since Sep 2026 $781,000 · 5 bd · 4 ba · 2,670 sqft
• 14501 grove resort avenue 3429, Winter Garden 34787 Off market since Sep 2026 $298,900 · 3 bd · 2 ba · 1,396 sqft
• 8016 sweet orange avenue, Winter Garden 34787 Off market since Aug 2026 $537,900 · 4 bd · 3 ba · 2,084 sqft
• 13613 larsen lane, Winter Garden 34787 Off market since Sep 2026 $825,000 · 5 bd · 4 ba · 3,812 sqft
• 14501 grove resort avenue 2616, Winter Garden 34787 Off market since Sep 2026 $200,000 · 3 bd · 2 ba · 1,396 sqft
• 15607 sylvester palm drive, Winter Garden 34787 Off market since Sep 2026 $700,000 · 3 bd · 2 ba · 2,092 sqft
• 516 south highland avenue, Winter Garden 34787 Off market since Sep 2026 $495,000 · 3 bd · 2 ba · 1,716 sqft
• 14200 avalon road 409, Winter Garden 34787 Off market since Sep 2026 $215,000 · 2 bd · 2 ba · 1,253 sqft
• 14542 black cherry trail, Winter Garden 34787 Off market since Sep 2026 $575,000 · 4 bd · 3 ba · 2,234 sqft
• 15537 mango isle street, Winter Garden 34787 Off market since Jul 2026 $690,000 · 4 bd · 4 ba · 2,909 sqft
• 3286 mainsail court, Winter Garden 34787 Off market since Sep 2026 $879,000 · 5 bd · 4 ba · 4,293 sqft
• 10301 austrina oak loop, Winter Garden 34787 Off market since Jul 2026 $525,000 · 3 bd · 3 ba · 2,078 sqft
• 7542 summerlake groves street, Winter Garden 34787 Off market since Sep 2026 $610,000 · 5 bd · 3 ba · 2,638 sqft
• 7030 twilight bay drive, Winter Garden 34787 Off market since Sep 2026 $469,000 · 4 bd · 4 ba · 1,920 sqft
• 13978 lanyard way, Winter Garden 34787 Off market since Sep 2026 $879,900 · 5 bd · 4 ba · 3,687 sqft
• 13181 toolcross way, Winter Garden 34787 Off market since Sep 2026 $999,000 · 5 bd · 4 ba · 3,310 sqft
• 16277 honey harvest street, Winter Garden 34787 Off market since Aug 2026 $668,000 · 4 bd · 5 ba · 2,930 sqft
• 15591 gentle rain drive, Winter Garden 34787 Off market since Sep 2026 $679,900 · 5 bd · 4 ba · 2,896 sqft
• 181 zachary wade street, Winter Garden 34787 Off market since Aug 2026 $600,000 · 5 bd · 3 ba · 2,940 sqft
• 5973 cypress hill road, Winter Garden 34787 Off market since Sep 2026 $694,000 · 5 bd · 4 ba · 3,532 sqft
• 13843 lanyard way, Winter Garden 34787 Off market since Jul 2026 $614,000 · 4 bd · 4 ba · 2,568 sqft
• 12253 south bracco street, Winter Garden 34787 Off market since Sep 2026 $499,000 · 3 bd · 3 ba · 1,788 sqft
• 420 east cypress street, Winter Garden 34787 Off market since Sep 2026 $410,000 · 3 bd · 2 ba · 1,616 sqft