Honestly, I doubt that will be the case. Chris hates living in the hoard and the only thing keeping him there is Barb and the lack of current options.
My best guess is that when Barb dies and he's grieved enough, Chris will pack up his stuff and leave 14 Branchland Court for good and entirely of his own volition too.
What happens after that is anyone's guess, although I do think homelessness will definitely be part of it. Whether it will be permanent or temporary is anyone's guess.
Before the Idea Guys happened and the merge stuff started, I figured some white knights or some of his IRL asspatters in the LGBT and nerd scenes would help him find some cheap ratty apartment or trailer to live in and subsist on his tugboat and at most, he may have to spend a few nights sleeping in his car or couch surfing.
Nowadays, I think he'll end up permanently homeless by the end of it unless the shock of Barb's death is so big that it snaps Chris into reality. However, I'm not holding my breath on that one.
As for what happens to the house after the bank repossesses it, I'd say they would try to sell it and whoever buys it will probably demolish the house and flip the property some other way.