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Milton seems like perhaps the best fit. The red line (mattapan connector) goes there, and it's got access to the south. Needham to South Station alone takes something like 45 minutes (who knows why, except the route loops around) and with an added ride to Cambridge it's over an hour.
Something near the Auburndale, West Newton, or Newtonville stops on the Framingham line has quicker train access to South Station than Needham, but it's still probably 45 mintues one way to Cambridge. Auburndale is very nice and is closest to 128 for the drive south, but 128 is not much fun. It can be very slow. Anything else in Newton (say along the D line) would take too long to downtown Boston for the switch to the Red Line).
Norwood is OK, a nice downtown area (real small town USA feel) but the schools might be better in Westwood, which also has a pretty quick ride to South Station from the 128 stop. It's something like 20 mins. You can go through Norwood from Westwood to 95 South. Westwood's a bit more woodsy but Norwood's pretty quiet too.
I like Watertown a lot but I wouldn't want to commute to Easton from there.
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