... just because stone buildings are rare, don't rule them out. Many of your wealthier folks had large stone buildings, especially from the 1800's on... Your second pic from the top would be a fine example...
My thoughts exactly, that screams Boston Old Money to me. Exactly the sort of people who would never pahk the cah in the Hahvard yahd.
Interestingly I just saw a piccy of the rebuilt Governer's House in Williamsburg, Virginia... the Governer's House is a lot bigger and has a weird tower in the middle of its roof, but there are definitely similarities (google 'williamsburg governor's house' and I'm sure you'll see what I mean).
I like the plank church and the two shacks too. They look like they'd fit right in.