Winter Garden neighborhoods with the market data that actually moves a decision.
411 Winter Garden community guides, each with real pricing, HOA/CDD reality, and flood/insurance posture. Below: the Winter Garden market snapshot, then every community we cover.
All Winter Garden communities (411) · page 2
Winter Garden ManorWinter Garden Manor in Winter Garden, FL: 7,786 homes for sale in Orange County (24% under contract), 7 MLS sales on record since 2006.Winter Garden ShoresWinter Garden Shores in Winter Garden, FL: 80 homes built 1928–2019, ~1,718 sq ft, 3 bd/2 ba. ZIP 34787 median $595K, 357 for sale.Winter Garden ShoresWinter Garden Shores in Winter Garden, FL: 453 homes, built 1906-2024. Live Stellar MLS data and public records.Winter Garden Shores RepWinter Garden Shores Rep in Winter Garden, FL: Recent sales median $500K (2025), $378/sq ft, 46 sales since 2005. Live Stellar MLS data and public…Winter Garden TrailsWinter Garden Trails in Winter Garden, FL: Median sale $485K (2026), median 29 days on market. Live Stellar MLS data and public records.Winter GroveWinter Grove in Winter Garden, FL: Median sale $1.08M (2026), 11 homes, built 2024-2024, median 0 days on market. Live Stellar MLS data and public…Winter GroveWinter Grove in Winter Garden, FL: Median sale $1.15M (2026), median 0 days on market. Live Stellar MLS data and public records.Winter OaksWinter Oaks in Winter Garden, FL: Median sale $678K (2026), median 32 days on market. Live Stellar MLS data and public records.Wintermere HarborWintermere Harbor in Winter Garden, FL: 59 homes built 1999–2003, ~2,852 sq ft, 4 bd/3 ba. ZIP 34787 median $595K, 357 for sale.Wintermere PointeWintermere Pointe in Winter Garden, FL: Median sale $560K (2026), median 16 days on market. Live Stellar MLS data and public records.Woodbridge On GreenWoodbridge On Green in Winter Garden, FL: Median sale $630K (2026), 56 homes, built 1987-2015, median 39 days on market. Live Stellar MLS data and…