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==Transportation== [[Image:A-V north at Conroy.jpg|thumb|right|Signs on [[Apopka-Vineland Road]], {{convert|1.5|mi|abbr=on}} 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 {{convert|7.5|mi|abbr=on}} distant at [[Lake Buena Vista, Florida|Lake Buena Vista]], where County Road 535 (CR 535) and [[Apopka-Vineland Road]] meet. The next crossing to the north is at [[Gotha, Florida|Gotha]], the north end of the chain of lakes, {{convert|2.25|mi|abbr=on}} away. 2003 [[Annual Average Daily Traffic]] (AADT), much of which is [[commuter]]s 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.{{update inline|date=April 2023}} Windermere [[traffic calming|regulates traffic]] and encourages traffic to use alternate routes.{{citation needed|date=May 2015}} 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 (road)|grid]]) are [[dirt road]]s except for a few through roads: *Main Street from the northern boundary (as Maguire Road, which heads north to [[Ocoee (FL)|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 [[annexation|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 [[Florida State Road 439|State Road 439]]. This was given to [[Orange County, Florida|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 [[Florida State Road 50|SR 50]], but no other signs exist, in part because Orange County has a general policy of not signing [[county road]]s. The [[Florida Midland Railroad (defunct)|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.<!--at which street?-->
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