Windermere Town Logo

That's Windermere, Florida albeit their town logo (apparently what they call it) is inspired by Windermere England. The explanation I have found is:

1. The boats represent 3 Windermere class yachts.
2. The black and yellow cross hatch in the top right represents an ancient gate which denotes Windermere UK as being the gateway to the Lake District.
3. The red cross on the white background is the flag of St George,/ England.
4. The fish are 3 Char which is a rare breed of trout only found below 90ft in Lake Windermere (England's largest natural lake)

The Schoolhouse has its own explanation.