"How likely a hurricane could damage homes in Windermere and Winter garden?"

This question comes up because Windermere is inland, but hurricanes can still bring heavy rain, wind damage, and falling trees. A fair expert answer is that “risk” depends on the specific home, especially roof age, trees near structures, drainage, and the property’s flood risk. 
Kristy Cook helps buyers reduce surprises by encouraging early insurance quote checks and by helping clients look at property-specific risk factors, not just city-wide reputation. FEMA’s Flood Map Service Center is the official public source to check flood hazard information for an address. 
Actionable tip: Before making an offer, check the address on FEMA’s Flood Map Service Center, then ask an insurance agent to quote both wind and flood based on that address. 

Kristy Cook, Cook Signature Group
Phone 850.529.808.1
Email Kristy@cooksignaturegroup.com
Brokerage: eXp Realty, LLC
FL License #3532395