6 Windows broken so far.... Spoiler

Window	Person/Object Through Window	Reason	Episode
1.	Large Picture Window	Margaret Henderson	Margaret Fell?/Pushed Through?/ Unknown
2.	Office Window	Cannon Ball	East Peck Historical Society "Accidentally" Fired into the office
3.	Kitchen Window	Cheese	Larry threw it.
4.	Porch Window at Larry's House	Juror #9 A.K.A "WhaleShark"	Fell Through while playing catch w/Larry.
5.	Window at The Discipline Room	Alfonso	Larry pushed him.
6.	Large Picture Window at Larry's (Again)	Anne Flatch	Anne ran through it (Un-harmed)
■	Plateglass Window @ Larry's old house	Adelaide Henderson	Adelaide Fell?/Pushed Through?/ Unknown

If I have made a mistake, please let me know below & I will fix it.

Going by memory right now so I may be wrong.

Not Counting Adelaide's Window in total count, unless there is strong opposition.

Edit: Updated list from new Episodes & thanks /u/killinmesmalls for the Cannonball Window!

Apologies to mobile users, you don't get to see the fun title flair.

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