P.R.
If you want to look in NYC or near - Try contacting moms in the NYC area for up to the minute ideas on the best places to live - Baby Bites is an excellent online resource. I think you can post your question there too.
http://www.babybites.com/about/about-us/
This site provides great overview of things to do in NY and different neighborhoods.
http://newyorkkids.timeout.com/
New York magazine had an excellent article about this October 7, 2002 - "10 Suburbs you can afford" - nice neighborhoods, good schools, easy commutes. This might be a good starting point.
- Montclair, NJ - 29 min to Penn station
http://nymag.com/nymetro/realestate/features/affordable20...
- Maplewood, NJ - 20 miles to midtown Manhattan, 25 to 35 min to Penn
http://nymag.com/nymetro/realestate/features/affordable20...
- Katonah, NY - 46 miles to midtown Manhattan, about 1 hour commute
http://nymag.com/nymetro/realestate/features/affordable20...
- Dix Hills, NY - 36 miles to " ", about 1 hour to Penn
http://nymag.com/nymetro/realestate/features/affordable20...
- Montville, NJ - 33 miles to " ", about 50 min to Penn
http://nymag.com/nymetro/realestate/features/affordable20...
- Ossining, NY - 36 miles to " ", about 48 min - 1 hour to Penn
http://nymag.com/nymetro/realestate/features/affordable20...
- Pelham, NY - 17 miles to " ", about 29 min to Grand Central
http://nymag.com/nymetro/realestate/features/affordable20...
- Larchmont, NY - 21 miles to " ", about 40 min to Grand Central
http://nymag.com/nymetro/realestate/features/affordable20...
- Cold Spring Harbor, NY - 35 miles to " ", about 1 hour to Penn
http://nymag.com/nymetro/realestate/features/affordable20...
- Milford, CT 66 miles to " ", about 90 min to Grand Central
http://nymag.com/nymetro/realestate/features/affordable20...
If you don't have children or even small ones, or an older couple, Stamford, CT is very nice, with a good mix of affordable residential homes and apartments, stores (Target, Macys @ Stamford Town Center mall), nightlife, express trains into NYC (45 minutes) and good (not great) beaches. The downtown area has undergone an amazing transformation in recent years, attracting the likes of Donald Trump who built a high rise luxury residential building there. The only minus: public schools are not as good as other places (if you have school age children).
Old Greenwich, (part of Greenwich CT) is also very nice with small-town feel, great public schools, popular with young families with kids as well as older couples. Downtown Greenwich is more cosmopolitan with larger stores (such as Saks), lots of restaurants, and apartments, attracts a younger crowd. Byram has smaller, more affordable houses (starter homes) but as with all the other subdivisions, it has access to all the town of Greenwich has to offer for its residents including state-of-the art libraries, free concerts, parks and a wonderful beaches. Greenwich Hospital and Greenwich High School are both excellent. There are five train stations in town, stay close to them if you have no car but other than than, many choices and good prices now.
http://www.greenwichct.org/Home/default.asp
If checking out schools, these are helpful links:
http://www.schoolmatters.com/
http://www.savvysource.com/