Welcome To Windermere Crossing,  Winter Garden, Florida 34787 Presenting Windermere Crossing entrance marquee. Windermere Crossing is located in the Town of Winter Garden, which is in Orange County Fl.,  Winter Garden is known as "A charming little city with a juicy past". Located 14 miles from downtown Orlando. It should not be difficult to find the right property for you, many short sale and foreclosure opportunities. Lets get started today and find the real estate that you have been waiting for. Buying or selling your home in Windermere Crossing we can assist you! Facing a foreclosure? Try a short sale! We can help! Call today for VIP service. Windermere Crossing Community Quick Facts!  Neighborhood established on August 20, 1999 This community consist of 156 home sites As of 2010 HO... 11/22/2010