Afterlife: The Jewish View: Where are we headed? by Jonathan Morgenstern is a certain take on the Jewish system of the afterlife, if we say there is a system at all. Unlike Christianity, where the idea of an afterlife (can be) extraordinarily important, in Judaism, it is important but carries less weight. Most Jews, particularly secular or progressive, have little idea of speculations of Jewish life beyond death.
I don’t agree with Morgenstern’s theology or worldview, but if you want a pretty short book to give you a picture of the Jewish afterlife, this is not too bad. Just don't think it is the only one in town.