Windward Cay
Windward Cay: Local Questions Answered
Where is Windward Cay in Winter Garden?
Windward Cay is off Tilden Road near Winter Garden Vineland Road, on Turningwind Lane, Zephermoor Lane, Tempest Way and Sirocco Drive. It is inside City of Winter Garden limits.
What types of homes are in Windward Cay?
Windward Cay has 66 single-family homes built from 2002 to 2004, according to Orange County Property Appraiser records. Homes range from about 2,350 to 3,860 square feet on lots of about 0.24 to 0.42 acre; 48 are two-story and 18 are one-story. There are no townhomes.
How much do homes cost in Windward Cay?
Four homes in Windward Cay sold over the past two years (MLS data, October 2026). Based on those four sales, the median was about $778,000, and prices ranged from about $756,000 to $998,000. For today's listings, see the top of this page.
What are the HOA fees in Windward Cay?
Recent MLS listings show HOA dues of about $110 to $115 per month as of October 2026. Orange County property records and Florida's official list of special districts don't show a community development district (CDD) for Windward Cay, but check the property tax bill for any special assessments. The association is Windward Cay - Winter Garden - Homeowners Association, Inc.
What schools serve Windward Cay?
Orange County Public Schools' 2026-27 school zones place Windward Cay in Keene's Crossing Elementary, Bridgewater Middle and Windermere High School.
Zoning can change and varies by street, so confirm a specific address with Orange County Public Schools' Find My School tool, and compare school grades in the Florida School Accountability Reports.
Is Windward Cay gated, and is it the same as Windward Cay East?
Realtor sites and MLS listings describe Windward Cay as a gated community. Windward Cay East and Windward Cay Office Park are separate commercial plats of office and retail space on Tilden Road and Winter Garden Vineland Road. Windward Cay is the 2001 residential plat of 66 homes.
Can you rent homes in Windward Cay short term?
No Windward Cay-specific rental rules turned up in our research. HOA documents often limit leasing, so confirm the current rules with the association before buying if you plan to rent.
