I agree it exists as an option that’s between Stamford and New Haven in feel, but not sure what you mean by more amenities? Like big box and mall shopping? New Haven still has it beat on city attractions.

It depends what you’re comparing to. Compared to New Haven, yes, a bit more family oriented. Compared to any other suburb in CT we’ve lived in, not at all.

We are a childless couple, in our late 30’s. We have other childless couples or singles in town we are friends with. Many I previously worked with who chose the town. The town is very popular for first time homebuyers, and is having a small apartment boom right now. It’s appealing to Millennial buyers because it’s relatively affordable for a southwestern coastal town (much cheaper than Fairfield), has good schools (unlike nearby Stratford and West Haven), has low taxes (unlike nearby Stratford and West Haven), low crime, good walkability (great downtown, and other walkable centers). There’s 3 breweries in town, independent coffee shops, good food. I was talking to a restaurant owner that had their location in Branford previously, and they mentioned how much more buzzing and young the town feels.

There’s also a lot of beaches, parks, a boardwalk, a nature sanctuary, tons of sporting facilities (tennis courts, pickle ball, etc). People are always out in the warm months jogging, biking, walking their dogs.

We are a 15 minute drive to New Haven. So we go 1-2 times a week to eat out, walk around, visit coffee shops, take in culture, see a show. Could also take the train just as easily, which, is super easy to access downtown.

Again, compared to most CT suburbs, this isn’t one of the dead ones full of homebodies.

New Haven is great. You should definitely consider buying in East Rock. But if you want a lower tax sibling on the coast that’s got some liveliness, it’s Milford. In fact, while I love Westville, it’s not super convenient to the rest of New Haven and I’d probably recommend Milford over that.

This site is a great summary: https://discovermilfordct.com

Also, I see you edited your original post to include West Haven. West Haven is great for those on a tight budget. The area of West Haven near Milford, West Shore, is a bargain. The rest of West Haven is fine, but a little rough around the edges. The city has serious financial issues, now the state is having to get involved. Again, it’s a good bargain. Taxes are high. Schools aren’t great, which affects resale. I’m not sure I’d ever recommend it over Milford, unless you were looking for cheap coastal housing in West Shore.