Top Definition
The rich small "town" very close to Orlando. The area is not much more than a lot of trees with large gated subdivisions that house many celebrities and rich families sending their kids to private school, and in the center of it all is a small ice cream shop that can "rip you off" because it is the only place to eat anything in the area and has wealthy costumers.

Usually taking a walk around these streets you see white and black Escalades, Lincoln Navigators that are driven by the wife of a rich man who is working during the day so they drive around windermere wearing sunglasses and hang out with other women that live similar lifestyles.
"That lady in the Escalade driving in Windermere is hot"

Friend: "Watch it that's Donald Trump's Wife"
by chachaboi December 13, 2011
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