Windermere was established in 1889, and works hard to retain a small town feel. It was once the hometown of famous professional golfer Tiger Woods. However, many celebrities such as Woods actually live in the Isleworth gated community/subdivision which is actually outside the city limits of Windermere but utilize the Windermere mailing address
Windermere is located in a narrow place 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 7.5 miles (12 km) south 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, 2.25 miles (3.5 km) to the north.
Windermere tries to regulate traffic and encourage traffic to use alternate routes. Some of Windermere's traffic calming techniques, including limiting traffic to residents, have been determined to be illegal. 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 (SR 439). This was given to Orange County as 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.
Signs on Apopka-Vineland Road, 1.5 miles (2.5 km) east of downtown, warn heavy vehicles to stay out of Windermere.Three four-way stops were in the downtown area, all on Main Street - at Fifth Avenue, Sixth Avenue and 12th Avenue. The large amount of traffic during rush hours causes a great deal of congestion, especially as more housing developments are built west of Windermere (particularly the planned Horizon West New Urban community). In 2005 the stretch of main street between Seventh Avenue and Fifth Avenue was repaved in brick and the four-way stops at Sixth and Main and Fifth and Main, were replaced with circular, round-a-bout intersections which have eased traffic flow and added aesthetic value