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I can speak to Glen Ridge and Montclair.
Montclair is a very diverse town with two town centers that cater to different crowds. You have the upper Montclair section which is more family oriented with the hardware store, soda shop, etc. Then you have the section along Bloomfield Ave which is very hip, trendy and a great place to go if you are young, single or just want a night on the town.
The school is ranked ok, although it isnt stellar, and the taxes will not be inexpensive. The homes are generally well kept, older homes with a lot of character. Drive around the area though, because there are some spots of Montclair that are a little... rougher.
Glen Ridge borders Montclair and it is a very small "town." With picturesque streets and charming homes, this is a very wealthy town. The taxes are astronomical yet what it gives you are stellar schools (#4 in the state) access to everything in Montclair because its so close and transportation into the city. Both Montclair and Glen Ridge border Brookdale park, which is a great place to take a walk, throw the ball around, etc.
Livingston is a little more rural than Montclair and Glen Ridge and is farther East. If you were to ask me personally which I prefer more, I would say Montclair or Glen Ridge. I feel the homes are older, have more character, the downtown is far better (Montclair), the schools are better (Glen Ridge) and if you need to get into the city, Livingston is a major pain.
Just my opinion though, unfortunately I have no knowledge of S. Orange of Maplewood, but best of luck!
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