Main Street in the town of Windermere extends about 1 1/4 miles from it's southern end to where it becomes Maguire Road. The name change takes place over the canal which connects Lake Down to Wauseon Bay.
Main Street exists in many towns but few are like ours. Ours even has a side street named after it. Windermere is steeped in history and has retained quite a few of it's historic buildings. Just to the south of the southernmost roundabout is 7th Avenue. On this street about half a block west of Main Street you will see the first schoolhouse built in the city. On the southwest corner of the southernmost roundabout you will unfortunately see the new government building and Police Office. The old buildings have been removed.
The first or southernmost roundabout is where you will cross over 6th Avenue. This is also where 6th Avenue is divided between east and west 6th Avenue. 6th Avenue East eventually becomes Conroy Windermere Road and passes by The Grove Shopping Center.
The historic portion of Main Street in Windermere FL is between the two roundabouts and 5th and 6th Avenue. There is about 475 feet between the roundabouts and all of the historic portion is on the west side. Here is where you will find the Windermere Town Hall, Windermere Library and of course the weekly Farmers Market. On the corner of W 5th Avenue you will see residents playing basketball on a fairly regular basis. Also hidden away in this same area is the 9-11 memorial which is near the library.
Just to the north of the historic buildings you will often see town residents playing basketball as you drive through town. This is the norm in our small town. The court is just to the west off of Main Street on 5th Avenue. As for parking you can park along Main Street in designated areas. Once you leave Main be mindful of the signage. Some of the smaller businesses need the parking spots for their patrons.
The final interesting sight as you drive through town is the Park Among The Lakes. This is basically a group of three tennis courts which are quite often used. There is parking and you can easily be distracted by it as you drive by. It's normally about this time you will think about driving down some sideroads. Of course feel free but please keep in mind that some of the roads get narrow and are not paved. It's not that bad I have seen Bentleys and Ferraris on these same washed out roads. You may be surprised what you see just off of Main Street in Windermere FL.