Originally Posted by wideman

I believe that Davis Square in Somerville fits all/most of your criteria.

Lots of restaurants and bars, and a great walking neighborhood (including access to the bike/pedestrian path that goes all the way to Lexington and Bedford, 11 or 12 miles away). The housing in the neighborhood is primarily 2- and 3-decker houses: one floow is typically occupied by the owner, and each of the other floors is rented out. So you'd have the floor (usually 2 BR, living room, kithcen, possibly dining area, possibly porch) to yourselves. Parking is available either on-street or in the house's driveway. Also, Davis Sq is on the Red Line for great access to the city. Should be able to find very nice place for your budget.

Somerville isn't technically Cambridge or Boston or Brookline, but it's just as easy (in fact, easier in many cases than Brookline). Davis Sq itself is less than half-mile from the Cambridge line.