If you are going to be commuting to NYC from Waturbury, you should be prepared for a very long commute, which quite possibly could be approximately an hour and a half or more. Depending on your price point, you will be able to find homes in towns closer to NYC or commutable by Metro North train service. I have town and school info on my website http://www.HomesInFairfieldCountyCT.com in addition to free multiple listing service searches. Feel free to email me at Mary@HomesInFairfieldCountyCT.com or call me toll free at 888-335-3289.
Southern Connecticut is either going to be outrageuously expensive or questionable neighborhoods. Aside from those two options your third is to extend your commute by looking a bit more north. My personal suggestion is check out Pennsylvania if you are looking for an affordable commute to NYC.
Please visit my website DavidLemel.com and you will have all your answers. My job is to make my clients happy, and that is what I do. Please call me I would love to help you out. 203-671-7062-David Lemel
Are you open to considering other areas to live? There are areas in Queens that may fit your needs. Good neighborhoods, good schools, established bedroom community, parks, near the water, low real estate taxes, and no tolls to NYC.