Windermere town, Orlando

At Christmastime, go for a stroll at night on Main Street in Windermere. They have magical Christmas lights! Stop for an ice cream at Allen's Creamery, at 523 Main Street.

The rest of Windermere is cookie cutter developments. They generally have sidewalks, playgrounds, and walking paths but not much shade. Walking is a bit of a barren experience here though you do see some nice glimpses of nature. Near Windermere Trails development the walking trail takes you past a large lake with some old trees with Spanish moss. There are wildflowers and an occasional butterly. Sometimes it's pretty, other times it's quite stark- a strange mix. People tend to bike ride and jog in the early evening when the lack of shade doesn't matter as much.
There are several shopping centers with places to eat. I didn't really enjoy My French Cafe with the loud fridges inside and too many aggressive birds outside, though the chocolate croissant was well made. Bruster's Real Ice Cream, in a strip mall, is fun in the evenings when families come after dinner to have a treat. The cheerful high school students serve you at the window and then you sit on the picnic tables outside to eat.
There is a nice playground with a tall space net called Summerport Park. 
For a hike, check out rugged Tibet Butler Nature Preserve.

Directions

Allen's Creamery, 523 Main Street, Windermere FL 34786. This is the main street of old town Windermere.
These are at the cookie cutter developments:
Bruster's Real Ice Cream, 5855 Winter Garden Vineland Rd Ste 110, Windermere, FL 34786.
Summerport Park, 14442 Bridgewater Crossings Blvd, Windermere, FL 34786.

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