|The following is based on Van Buren and has not been confirmed by canon sources.|
The New Canaan sheriff's office was a building in New Canaan.
General-purpose sheriff's office/jail. Sheriff O'Connor can be found here with one deputy during the day (except in the early evening, when he is with Jeremiah in the outskirts).
New Canaan sheriff's office was going to appear in Van Buren, the canceled Fallout 3 by Black Isle Studios.