The most exclusive area of West Orange is Llewellyn Park, a historic gated community of homes. However, these homes are in the millions. There is currently one listing in this community that is $579k and the rest start at 1 mil.
Gregory is a popular area as the area has a shuttle bus to take commuters to the Mountain and South Orange Train Stations. Some streets are close enough to walk there. You can find homes with historic character including colonials starting at $350k. There are some other nice areas as well. You may also wish to take a look at the school report cards at http://www.psk12.com/rating/USindexphp/STATE_NJ.html or NJMonthly.com this may help you narrow down neighborhoods with the strongest schools.
West Orange is working to revitalize their downtown and some areas are close enough to downtown South Orange which is very cute but West Orange doesn't have a downtown like Hoboken.
Is West Orange the only area you are considering? I only ask because there are a small handful of towns that have a similar vibe to the downtown of Hoboken -with walkability, with a grown up suburbia feel. These include Westfield (which has a top ranking school system and train into NYC), Montclair (though I would live in Glen Ridge as it has one of the top school systems in the state and right next to Montclair so you get close access to their downtown), Morristown, even Madison, and depending on how far south you want to go: Fair Haven and Freehold. I'm sure there may be others but those are the ones that, in my experience (having also lived in Hoboken in my early 20s), really have the same vibe and walkability to a vibrant town center.
Sorry to give you more info than you asked for. Just thought it may be helpful to know based on what you described.
If I can be any further assistance, please don't hesitate to call me at 973-418-3427 or email at firstname.lastname@example.org
Mountain Resort Properties
You can find more information on commuting on the township website: http://www.westorange.org
I would be glad to show you any homes that fit your needs. Feel free to call or e-mail me and I can narrow down the choices to the ones that may be most suitable.
Van Der Wende Associates
76 East Main St., Little Falls, NJ 07424
973-818-8506 or 973-509-7887
973-785-8420 @ Ext. 282