First, congrats on the upcoming move. No doubt, the many neighborhoods and 'burbs of Boston can be overwhelming in a search. From the many responses already received, you may sense that there are many great choices in the area.
The one major question would be whether you would prefer being near the ocean, or would a river or large pond be fine? Also, in terms of commute, would you be able to use the commuter rail or MBTA? The latter as options can definitely expand your choices.
For history, beauty, and great downtown restauraunts, Concord is superb. The Colonial Inn is one of a variety of gourmet choices in the area. You can take a swim in Walden pond, or canoe in the rustic river. And, if you have any interest in hiking or birding, there are trails and an Audubon sanctuary to enjoy. Commuting to Boston, though, can be challenging on Route 2 in rush hour.
Newton is in closer proximity to Boston, has decent access to the river and canoeing in certain spots, and is well known for their excellent school system.
For the convenience of travel, though, you may want to consider Brighton or Watertown as well. Brighton is a neighborhood in the western part of Boston, and has canoe and kayak rentals nearby. On the weekends, the local park along the Charles is very popular. For Brighton, though, the local public schools are not as notable as the other towns and cities mentioned, but there are some private school options nearby.
Good luck with the search, and congrats on the relocation plans from the Windy City.