That's a good point about New Haven--I love New Haven and would spend a lot more time there if I lived 15-20 minutes away rather than 45.

You've mentioned Newtown a few times in your replies. I grew up nearby, and if you've seen houses in a good price range I think you should follow your instinct and check it out some more! A pretty main street (that goes hard for Halloween and Christmas lol), a pleasant walkable area in Sandy Hook, a handful of good restaurants, pleasant paved walking at Fairfield Hills, as much hiking nearby as you could want... My hometown is similar but all woods and I'm sometimes jealous of the relatively livelier center of Newtown. Then of course the convenience of these towns is just hard to beat. From Newtown you're a quick drive from the food and stores and recreation in Bethel (my favorite town 🥲--actually, move to Bethel), Danbury, Brookfield, Trumbull, Monroe... an hour and a half from NYC on 84, half hour from the train to NYC at Southeast (in NY state)... Seriously, you could also check out Bethel, though it's smaller-feeling than Milford. (I'd say Redding too, for maximum nature-convenience balance, but you specifically liked the sidewalk in Milford, and the housing market is maybe not great in Redding.)