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If working in Penn Station, you want to be on the Midtown Direct train line. This means NO switching trains and your train will go directly into Penn Station.
The towns in order from east=> west are: Maplewood, South Orange, Millburn, Short Hills, Summit, Chatham, Madison, Convent Station (Morris Twp), and Morristown. You are looking at about 40-45 min one-way from South Orange to 50 Madison to 55-60 Morristown (check the schedules for precise info). Maplewood and South Orange are more congested/urban suburbs, Short Hills is $$$, Chatham/Madison are very nice, Morristown is bigger and will have more condo options. For instance, I know there are condo communities in Convent Station. [Note: Montclair is not on this train line and is very urban]. Other possibilities are New Providence and Berkeley Heights (very simple train change in Summit... get off and get on the next train in 5min -- this is because NP, BH, etc are on the "Gladstone Branch" of the Midtown Direct Line. This is a MUCH simpler switch than dealing with the PATH from Newark etc). NP is right near Summit, so you get that downtown area.
I don't know much about the towns you asked about, but being from the south/out-of-state, I'd choose a town that has more transplants (most of the above do). Some other towns are going to seem more "Jersey".
Chatham, Madison, Convent Station/Morris Twp/ Morristown, New Providence, Berkeley Heights are all going to be quiet suburbs with excellent school districts...very different than the areas you saw (eg. Montclair which is more urban).
The towns in order from east=> west are: Maplewood, South Orange, Millburn, Short Hills, Summit, Chatham, Madison, Convent Station (Morris Twp), and Morristown.
For accuracy, here is a pdf of the morris-essex line w/ midtown direct. Times, cost etc...
Chatham, Madison, Convent Station, Morris Plains, Mount Tabor, Denville and surrounding areas are all good starting points for your search. I'm not too sure about schools in Morristown and Dover. Surrounding areas include Randolph, Rockaway, Boonton, Whippany, Parsippany. I miss my NYC commute. I was totally content doing an 1+ hours on a train.... my current commute of 45min by car is terrible by comparison.
I guess I simply prefer living west of 287 although that doesn't necessarily mean there are no good options east... slightly different feel to the area.
Cheap and very well located from a public transit perspective (the northwest corner of the park to the south of the town is a transfer point for a very large number of bus routes), but it's relatively dense for a suburb (both in built environment and people per house) and fairly low-income. Most of the residents are Hispanic immigrants.
It's a perfectly fine place to live if you're looking to save money - and it might be worth it to you, I was open to it [but went elsewhere] when I was looking for apartments in the area a few years back - but if you are looking for something that is "suburban feeling" with a charming downtown you will be happier elsewhere.
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