I love these old photo guessing games.
Ithink the Jail Annex was built around 1960, so it predates 1960. There's houses on the east side of Hudson Street north of Kansas Street, where One Bergen Center now stands. There is also houses on both sides of Court Street west of River Street. Help us on that, Ol' Homer. When were those houses torn down?
And perhaps the biggest clue, River Street itself exists. I know it was built in phases, and unsure when it was built around Lafayette St ?
My guess: 1940 - 1950.