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"
Mary Winkler was convicted of voluntary manslaughter in the 2006 shooting death of her husband, Matthew Winkler, the preacher at the Fourth Street Church of Christ in the small town of Selmer, Tennessee. She gained national attention due to public speculation about her motives and mental health, allegations of abuse by her husband, her brief flight from the state, and again for the brief length of her jail sentence. At the trial it became known that her husband made her wear stripper shoes and wigs during intercourse. After the trial she gained more national attention when the show “Snapped” aired a telling of her story and also when the Drive-By Truckers penned the song “The Wig He Made Her Wear,” including it on their 2010 album The Big To Do.
2) a euphemism for a crazy girl.