This advice is highly generalized, but hopefully will help you get started.

When you look at the map of MA - there is basically 3 rings of communities surrounding downtown Boston.

The first ring - Medford, Arlington, Watertown, Brookline - still high density, city vibe, easy public transit. Lots of multi unit houses, some single family. If proximity to the city is a priority, this is where you want to be.

The next ring - Lexington, Waltham, Wellesley, Needham - these are 'bedroom communities'. Lots of people work in Boston but want to raise their families in the suburbs. Primarily single family houses. Train access to the city, but you may have to drive to a station. Very family oriented communities with high priority on the school system. Houses cost $$$ here. Restaurants are OK, most places shut down at 9PM, almost nothing for nightlife.

The third ring - the outskirts - Burlington, Billerica, Bedford, Natick, Norwood. Further out from the city, will definitely have to drive to a train station or just drive into the city. More land. Housing prices drop a bit.

I've lived in Needham, Billerica, Waltham, Arlington and Dorchester. If I had to choose right now - I would pick Arlington.