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It definitely seems like Henry's dead by the end of the It remake. I mean, he falls down a pretty deep well. Still, this is a big change from the novel: in the book, Henry follows the kids down into the sewers with his two lackeys. They encounter It, and It turns into Frankenstein's monster. It then beheads one of Henry's goons and mauls the other. Henry goes insane and gets locked away in a sanitarium.
I believe Henry survives the fall only because he's a huge part of the adult story. If he does end up in the sequel, I think Matt Smith could take him on. They look really similar physically, and I just have a feeling Smith could really lean in to some evil tendencies.