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South Orange is def. comparable to Montclair. Diverse and vibrant. Also a college town. High taxes just like Montclair. 35 min direct train into NYC. Do not confuse it with other Oranges
If you are in love with Montclair, then by all means go to Montclair. I think, of New Jersey, Westchester and Long Island, NJ has the highest property taxes and the highest commutation costs on the train, however no amount of practical considerations can make up for the it factor of loving where you live.
Westfield, Cranford, Summit, Westwood and Clark in NJ. Great Neck, Manhasset in LI and Mamaroneck, Port Chester and White Plains in Westchester. South Orange is too close to East Orange and it's not so nice there.
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