Corrected entry: In season 1 when the camera zooms in on Cory and Eric's room, their window is shown on the front of the house. In other episodes Shawn has climbed through the window a number of times. He has done this from the tree house, but the tree house is on the side of the house by Feeny's yard.
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Correction: Their room is in the corner of the house. There easily could have been a window on the front and the side.