Windermere is a town in Orange County, Florida, in the United States. As of the 2000 census, the town population was 1,897. According to the U.S. Census Bureau's 2006 estimates, the town had a population of 2,019. It is part of the Orlando–Kissimmee Metropolitan Statistical Area. Windermere was established in 1889 and has been the residence of professional golfer Tiger Woods since 1997 as well as other professional sports figures. However, many celebrities such as Woods actually live in the Isleworth gated community/subdivision which is outside the town limits of Windermere, but utilize the Windermere mailing address. During late 2007, the Town of Windermere filed a proposal to annex Isleworth and Butler Bay, another wealthy subdivision. This was met with extensive debate from town residents and an objection from Orange County, which stood to lose millions of dollars of property tax revenue. After lengthy discussions, and battles with the county, Isleworth remained in the county, but Butler Bay was annexed into Windermere with over 90% of its residents approving annexation via a mail in ballot. Windermere is also home to famous cyclists, the Windermere Roadies, led by Sir Manny Otero of Winter Garden.