Jane DeVincentis and Karen Hoffman
It is unlikely that you will find a home in Madison for under $250,000. You can find a house in Morristown or Morris Plains possibly. Sometimes maybe even Chatham but at $350,000 and will need work. If you would like me to send you listings call me at (973)951-5859 and give me your e-mail address. I can send you what types of homes would be available. I grew up in Danbury , CT and my sister lived in Redding so know Connecticut well. If you want to come down for a preview trip let me know and I will take you around.
I am familiar with Enfield having lived just over the border in MA. Madison is more on par with Longmeadow. There are plenty of areas where you could find less expensive options. Morris Plains is a good bet. Feel free to contact me with any questions. Ncoffey@turpinrealtors.com