East/South Bay and Boston area (life, schools, downtown, rail)

[georgecostanza1472]

What is a cool suburb/town in the east bay, or south bay that is comparable to a Brookline or Newton in Boston; as in pretty homes, good walkable downtowns, not city-life but not totally boring.

There's so many stunning east bay towns I just don't know which ones are like hey you could be in town in 5 mins, and take public transit to SF with no problem... you are away from the city life, but aren't in the boonies.

[bugelrex]

Either San Mateo or Palo Alto or Cupertino is similar to Newton.
San Mateo because it has an ok downtown and lots of outdoor activity similar to some parts of Newton. Commuter rail to SF in around 25 mins, similar to T/Rail to Boston downtown
Palo Alto because it has many prestigious and historic homes
Cupertino because of the good schools