I would suggest that you look out toward Westchester County in White Plains area. Its a pretty straight shot into the city and not as pricey as some parts of CT. Also, long Island has much to offer but you probably want to look from Islip in toward Manhattan.
NJ is also a good value and the Path Train takes you straight downtown. Glenn Ridge & Montclaire are good. Really lots of place within an hour and your price range. Not sure about the square footage you are looking for, but definately 3 and 4 bedrooms can be had for that. Use Craigslist to get a feel for what is out there.