Windermere Residential Real Estate, Florida

The Town of Windermere is located in southwest Orange County, fourteen miles southwest of Orlando, six miles southeast of Winter Garden, two miles south of Ocoee, and approximately six miles north of Walt Disney World. Windermere is surrounded by sand bottom lakes. Lake Butler (the largest) is on the west, Lake Down on the east, and Lake Bessie on the southeast. By means of a system of canals, Butler, Down and six other lakes are connected to form what is known as the Butler Chain.

Windermere was established in 1889, and works hard to retain a small town feel. As of the 2000 census, the town had a total population of 1,897. According to the U.S. Census Bureau's 2004 estimates, the town had a population of 1,958.

As a small town, prideful of its character, Windermere tries to calm traffic and encourage traffic to use alternate routes. 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 are 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).