Agree Branford and Milford are “nicer” and Hamden taxes are insane (worse than New Haven) - but OP doesn’t have kids. My impression is that there are fewer childless middle aged couples in especially Branford as well as Milford, but could be wrong. They’re also further out from downtown New Haven, 95 can be a barrier sometimes. And school quality doesn’t matter as much (although a well-run town is a bigger deal and agree that Hamden is struggling right now in that area) But yeah, Branford and Milford are also good choices. Personally, if I wanted to buy in the suburbs, I’d rent in New Haven first, get some friends, then buy in the surrounding areas.