Sharon is the type of town you're looking for on that budget in that driving range (assuming favorable traffic conditions of course) to the airport

>We'd be looking for a house on a bit of land (up to an acre) with woodsy views. Not sure how viable that is in Boston suburbs but thought I'd throw it out there

Pretty viable e.g.

https://www.zillow.com/homedetails/66-N-Main-St-Sharon-MA-02067/57507064_zpid/

Historic home within walking distance to several restaurants in the town center, the town library, and the commuter rail to Boston/Providence RI. (No financial affiliation)

>great things/challenges about living in Massachusetts.

One of the restaurants in the town center is a vegan restaurant.