Homes under $1M in Winter Garden, FL

391 for sale · 1,436 homes listed · Updated September 27, 2026 · Page 15 of 29

• 427 regal downs circle, Winter Garden 34787 Active Under Contract $475,000 · 5 bd · 3 ba · 2,135 sqft
• 7618 bluejack oak drive, Winter Garden 34787 Active Under Contract $559,900 · 5 bd · 3 ba · 2,455 sqft
• 1424 scarlet oak loop, Winter Garden 34787 Active Under Contract $379,000 · 3 bd · 3 ba · 1,737 sqft
• 7179 spring park drive, Winter Garden 34787 Active Under Contract $535,000 · 4 bd · 3 ba · 2,272 sqft
• 1345 winter green way, Winter Garden 34787 Active Under Contract $225,000 · 2 bd · 2 ba · 1,259 sqft
• 2716 gorst road, Winter Garden 34787 Active Under Contract $859,000 · 5 bd · 5 ba · 3,935 sqft
• 5887 cypress hill road, Winter Garden 34787 Active Under Contract $450,000 · 3 bd · 3 ba · 1,810 sqft
• 2108 tillman avenue, Winter Garden 34787 Active Under Contract $849,000 · 5 bd · 4 ba · 3,078 sqft
• 16031 pebble bluff loop, Winter Garden 34787 Active Under Contract $550,000 · 4 bd · 4 ba · 2,487 sqft
• 1372 roxy lane, Winter Garden 34787 Active Under Contract $519,900 · 4 bd · 3 ba · 2,030 sqft
• 14145 creekbed circle, Winter Garden 34787 Active Under Contract $739,000 · 4 bd · 4 ba · 2,823 sqft
• 16644 point rock drive, Winter Garden 34787 Active Under Contract $569,500 · 4 bd · 4 ba · 2,434 sqft
• 14975 winter stay drive, Winter Garden 34787 Active Under Contract $770,000 · 4 bd · 3 ba · 2,662 sqft
• 809 burch avenue, Winter Garden 34787 Active Under Contract $749,999 · 4 bd · 5 ba · 3,543 sqft
• 8931 doddington way, Winter Garden 34787 Active Under Contract $479,000 · 3 bd · 3 ba · 1,944 sqft
• 1523 juniper hammock street, Winter Garden 34787 Active Under Contract $750,000 · 6 bd · 4 ba · 4,204 sqft
• 15579 honeybell drive, Winter Garden 34787 Active Under Contract $399,000 · 3 bd · 3 ba · 1,727 sqft
• 14501 grove resort avenue 3439, Winter Garden 34787 Off market since Jul 2026 $320,000 · 2 bd · 2 ba · 1,375 sqft
• 14501 grove resort avenue 3205, Winter Garden 34787 Off market since Sep 2026 $325,000 · 2 bd · 2 ba · 1,265 sqft
• 14501 grove resort avenue 1220, Winter Garden 34787 Off market since Sep 2026 $325,890 · 2 bd · 2 ba · 1,375 sqft
• 14501 grove resort avenue 3538, Winter Garden 34787 Off market since Sep 2026 $351,450 · 3 bd · 2 ba · 1,396 sqft
• 14501 grove resort avenue 1637, Winter Garden 34787 Off market since Sep 2026 $235,100 · 2 bd · 2 ba · 1,375 sqft
• 14501 grove resort avenue 1237, Winter Garden 34787 Off market since Sep 2026 $210,000 · 2 bd · 2 ba · 1,375 sqft
• 14902 arrena road, Winter Garden 34787 Off market since Sep 2026 $585,000 · 4 bd · 3 ba · 3,392 sqft
• 16353 lakelet alley, Winter Garden 34787 Sold on Jul 28, 2026 $444,990 · 3 bd · 3 ba · 1,567 sqft
• 18339 oliver twist way, Winter Garden 34787 Off market since Sep 2026 $650,000 · 4 bd · 3 ba · 2,931 sqft
• 14501 grove resort avenue 1707, Winter Garden 34787 Off market since Jul 2026 $325,000 · 3 bd · 3 ba · 1,544 sqft
• 14501 grove resort avenue 3406, Winter Garden 34787 Off market since Jul 2026 $204,000 · 2 bd · 2 ba · 1,265 sqft
• 9849 lost creek drive, Winter Garden 34787 Off market since Sep 2026 $990,000 · 5 bd · 4 ba · 3,910 sqft
• 5963 glory bower drive, Winter Garden 34787 Off market since Sep 2026 $505,000 · 3 bd · 3 ba · 2,128 sqft
• 14536 golden harbor lane, Winter Garden 34787 Off market since Aug 2026 $450,000 · 3 bd · 3 ba · 1,904 sqft
• 9493 emerald berry drive, Winter Garden 34787 Off market since Sep 2026 $989,000 · 4 bd · 4 ba · 3,211 sqft
• 8018 bowery drive, Winter Garden 34787 Off market since Sep 2026 $640,000 · 5 bd · 3 ba · 3,075 sqft
• 17865 adrift road, Winter Garden 34787 Off market since Sep 2026 $599,000 · 4 bd · 4 ba · 2,484 sqft
• 14501 grove resort avenue 2119, Winter Garden 34787 Off market since Jul 2026 $224,000 · 3 bd · 2 ba · 1,396 sqft
• 14501 grove resort avenue 2623, Winter Garden 34787 Off market since Sep 2026 $390,000 · 2 bd · 2 ba · 1,265 sqft
• 10007 little alcove loop, Winter Garden 34787 Off market since Sep 2026 $960,000 · 4 bd · 4 ba · 2,921 sqft
• 14501 grove resort avenue 3202, Winter Garden 34787 Off market since Sep 2026 $350,000 · 3 bd · 2 ba · 1,396 sqft
• 11045 bostwick alley, Winter Garden 34787 Off market since Aug 2026 $575,000 · 4 bd · 4 ba · 2,292 sqft
• 16555 wingspread loop, Winter Garden 34787 Off market since Sep 2026 $791,000 · 4 bd · 4 ba · 3,093 sqft
• 14501 grove resort avenue 2334, Winter Garden 34787 Off market since Sep 2026 $274,900 · 3 bd · 2 ba · 1,396 sqft
• 9605 lost creek drive, Winter Garden 34787 Off market since Sep 2026 $699,000 · 4 bd · 3 ba · 2,117 sqft
• 15506 honey mandarin way, Winter Garden 34787 Off market since Jul 2026 $889,000 · 5 bd · 5 ba · 3,408 sqft
• 15280 maritime pine drive, Winter Garden 34787 Off market since Sep 2026 $979,990 · 6 bd · 4 ba · 3,550 sqft
• 10534 tribute drive, Winter Garden 34787 Off market since Sep 2026 $419,000 · 3 bd · 3 ba · 1,636 sqft
• 10540 tribute drive, Winter Garden 34787 Off market since Sep 2026 $419,000 · 3 bd · 3 ba · 1,636 sqft
• 15695 grove resort avenue 4417, Winter Garden 34787 Off market since Sep 2026 $150,000 · 1 ba · 350 sqft
• 14327 wabasso loop, Winter Garden 34787 Off market since Sep 2026 $869,990 · 5 bd · 4 ba · 3,710 sqft
• 17552 lake star road, Winter Garden 34787 Off market since Sep 2026 $999,000 · 4 bd · 4 ba · 2,605 sqft
• 14501 grove resort avenue 1440, Winter Garden 34787 Off market since Sep 2026 $245,000 · 2 bd · 2 ba · 1,375 sqft