Browse Windward Cay Homes for Sale in Winter Garden, FL. Discover community amenities, nearby attractions, schools, and the lifestyle this neighborhood offers.
Windward Cay Homes for Sale
Windward Cay Home for Sale
Windward Cay – Winter Garden
Windward Cay is a gated community of single-family homes located off Tilden Road, just west of Winter Garden Vineland Road, in the Central North area of Winter Garden. Built primarily between 2003 and 2004 by Engle Homes of Orlando, this neighborhood is known for its spacious floor plans, three-car garages, and quiet setting surrounded by conservation areas.
Residents enjoy close proximity to the West Orange Country Club and convenient access to the 429 Expressway, providing an easy commute to Walt Disney World, I-4, the Florida Turnpike, and Northwest Orlando in Lake County.
Windward Cay Neighborhood Amenities
Windward Cay features a mandatory HOA that maintains:
• Sidewalks
• Gated community setting
Where Is Windward Cay in Winter Garden?
Windward Cay is located in the 34787 zip code within the Central Winter Garden Village area.
Neighborhood Borders:
North: Wintermere Pointe
South: Conservation land
East: Sunset Lakes
West: Conservation land
What’s Around & Nearby?
Grocery & Dining: Cornerstone at Summerport
Shopping: Winter Garden Village
Hospital: AdventHealth Winter Garden
Schools: Orange County Find My School
Attractions: Walt Disney World & Universal Studios
Outdoor Recreation: West Orange Trail
Local Hangout: Downtown Winter Garden
Closest Beach: Cocoa Beach
Typical Windward Cay Home Features
Home features commonly found in Windward Cay (may vary by property):
Builder: Engle Homes of Orlando
Architectural Styles: Contemporary & Florida
Bedrooms: 4–6
Garage: 3-car
Living Area: Approx. 2,400–3,900 sq. ft.
Interior Rooms:
Separate breakfast room
Den / home office
Family room
Formal dining room
Formal living room
Inside utility
Average Lot Size: Quarter acre
Construction: Shingle
Roof: Shingle
Exterior Features:
Fenced yards
Irrigation system
Lighting
Rain gutters
Sidewalks
Sliding doors
Sprinkler metered
Select homes with garden or wooded views
Thinking about a home in Windward Cay?
Call or text the Jared Jones Real Estate Team at 407-706-5000 to learn more today!
Winter Garden Areas
Downtown Winter Garden Area Neighborhoods
Winter Garden Village Area Neighborhoods
Estates Lakeview Preserve
Wintermere Harbor
Wintermere Pointe
Woodbridge on the Green
Horizon West Area Neighborhoods
Avalon Cove
Cove At Hamlin
Del Webb Oasis (NEW)
Enclave at Hamlin
Encore at Ovation
Hamilton Gardens
Hamlin Reserve
Hawksmoor
Harvest at Ovation
Highland Ridge
Highlands Summerlake
Independence
Isles Of Lake Hancock
Lake Hancock Preserve
Lakeshore
Lakeside at Hamlin
Lakeview Pointe
Lakeview Preserve
Latham Park
Mezzano
Orchard Hills
Orchard Park
Osprey Ranch
Overlook At Hamlin
Panther View
Ravenna
Sanctuary at Hamlin
Storey Grove
Summerlake
Summerlake Groves
Waterleigh
Watermark
Westhaven Ovation
Wincey Groves
Winding Bay
Hamlin Pointe
Hamlin Ridge
Horizon Isle
Lake Star at Ovation
Northlake at Ovation
Parkview at Hamlin
Serenade at Ovation
Silverleaf Oaks
Silverleaf Reserve
Tribute at Ovation
Oakland Area Neighborhoods
Deer Island
Downtown Oakland
Hull Island
Johns Cove
Johns Landing
Lake Apopka Sound (NEW)
Longleaf at Oakland
Oakland Hills
Oakland Park
Oakland Trails
Trailside Station
Tucker Oaks
Verde Park
213 S Dillard St. Suite 320F,
Winter Garden Fl 34787
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