A post office opened in Windermere in 1888.[5] The post office closed in 1901, and reopened in 1911. Windermere was established as a residential development in 1889 and chartered in 1925.[citation needed]
During late 2007, the town of Windermere filed a proposal to annex Isleworth and Butler Bay, both wealthy subdivisions. 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 unincorporated, but Butler Bay was annexed into Windermere, with over 90% of its residents approving annexation via a mail-in ballot.
According to the United States Census Bureau, the town has a total area of 1.57 square miles (4.07km2), of which 1.56 square miles (4.03km2) is land and 0.015 square miles (0.04km2), or 0.98%, is water.[6]
As of the 2020 United States census, there were 3,030 people, 1,426 households, and 1,047 families residing in the town.[11]
The types of households in the town, in 2015–2019, were 75.6% married couples with families, 2.2% cohabiting couples, 12% male householders with no spouse, and 10.2% female householders with no spouse.[12]
As of the 2010 United States census, there were 2,462 people, 875 households, and 770 families residing in the town.[13]
Government
These signs appear on light poles at borders of the business district at the center of downtown.
Windermere has a Town Manager / City Council form of government. Five council members are elected at large for two-year terms with three running for election in odd years and two running for election in even years along with the mayor.
Police services are provided by the Windermere Police Department.[14] In January 2014, the department's former chief, Daniel Saylor, was sentenced to eight years in prison for perjury. He had lied to the court in order to protect a friend who was found guilty of raping children and sentenced to life in prison. Saylor had pleaded guilty to other charges in 2011, earning him a year in jail.[15]
Fire rescue and emergency medical services[16] are provided by the Ocoee Fire Department. Postal services are provided by the Windermere Post Office.[17] The Floridan Aquifer is Windermere and Orange County's source of drinking and fire hydrant water, which is filtered naturally through hundreds of feet of sand and rock, and then treated by the Orange County Water Division.[18]
The town of Windermere is not within the attendance boundaries of Windermere High School, a Lake Butler high school which opened in 2017.[19][24] The Windermere town council opposed the naming on the grounds that area residents may mistakenly confuse the school with Windermere Preparatory. Some OCPS board members also argued the school should not be named for a community it will not be located in; they stated that not very many students from the town of Windermere will go to Windermere High.[25]
Transportation
Signs on Apopka-Vineland Road, 1.5mi (2.4km) east of downtown, warn heavy vehicles to stay out of Windermere.
Windermere is located on an isthmus between several lakes in the Lake Butler chain. As such, it is on the shortest road route between the east and west sides of the chain. In fact, the next crossing to the south is 7.5mi (12.1km) distant at Lake Buena Vista, where County Road 535 (CR 535) and Apopka-Vineland Road meet. The next crossing to the north is at Gotha, the north end of the chain of lakes, 2.25mi (3.62km) away. 2003 Annual Average Daily Traffic (AADT), much of which is commuters passing through, is 17,197 vehicles per day for Sixth Avenue (the east entrance), 18,362 on Main Street north of Sixth Avenue, and 9,484 on Main Street south of Sixth Avenue.[needs update]
Windermere regulates traffic and encourages traffic to use alternate routes.[citation needed] In 2004, two roundabouts were installed downtown with the largest public works project in the town's history. This has greatly improved traffic flow and relieved cut through traffic. A third roundabout was completed in August 2010 at the intersection of Park Avenue and Maguire Road. This is at the Windermere Elementary School intersection. All roads in the downtown area (laid out in a grid) are dirt roads except for a few through roads:
Main Street from the northern boundary (as Maguire Road, which heads north to Ocoee) south to 12th Street; the pavement turns west at 12th Street onto Chase Road, which connects to CR 535
Sixth Avenue east from Main Street to the town line, where it becomes Conroy-Windermere Road
Second Avenue west from Main Street (serves a peninsula)
"Dirt Main Street", just west of Main Street (opposite where the railroad used to run), from Third Avenue to Seventh Avenue
Several other paved roads exist in the outskirts, in areas that have been annexed since the original town was formed.
Until the 1980s, Main Street north of Sixth Avenue and Sixth Avenue east of Main Street were maintained by the Florida Department of Transportation (FDOT) as part of State Road 439. This was given to Orange County as County Road 439 (CR 439), and Orange County eventually removed all signs and gave the part inside Windermere to the town. Signs put up by FDOT still mark the north end of CR 439 at SR 50, but no other signs exist, in part because Orange County has a general policy of not signing county roads.
The Florida Midland Railroad, part of the Atlantic Coast Line Railroad, used to run just west of Main Street; there is now a large grassy area between Main Street and the dirt road (often called Dirt Main Street) that ran just west of the railroad. Windermere had a station on the railroad.
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