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Give Stamford a try. Pros: It is a large city with a small town feel. Nice beaches with nice neighborhoods with great Metro North train access. It's 45 mins by train to Grand Central. Con: It is growing fast and the middle class is being pushed out--it is becoming "Manhattanized." It's also becoming pricey for home ownership--depending on where you buy.
If you can afford Fairfield, do it! Based on your writeup I would recommend looking around the Post rd near the train station. In this area you can walk to coffee houses, borders, resturaunts, a small movie house, and tons of other small shops and a few bars. Not to mention walking to the train to take it into manhatten for the night. From this area you can also bike ride to the beach. I think it would suite you just fine but it is pricey.
As for the more urban feel, the suggestions on Stamford and maybe even South Norwalk should do you well.
If you can afford Fairfield, do it! Based on your writeup I would recommend looking around the Post rd near the train station. In this area you can walk to coffee houses, borders, resturaunts, a small movie house, and tons of other small shops and a few bars. Not to mention walking to the train to take it into manhatten for the night. From this area you can also bike ride to the beach. I think it would suite you just fine but it is pricey.
As for the more urban feel, the suggestions on Stamford and maybe even South Norwalk should do you well.
+1 on Fairfield
I lived there for 8 years and enjoyed it. We found ourselves priced out of upgrading to a large enough home to start a family and ended up relocating.
Be prepared to spend $300 per square foot on a non-updated older home.
If you can afford Fairfield, do it! Based on your writeup I would recommend looking around the Post rd near the train station. In this area you can walk to coffee houses, borders, resturaunts, a small movie house, and tons of other small shops and a few bars. Not to mention walking to the train to take it into manhatten for the night. From this area you can also bike ride to the beach. I think it would suite you just fine but it is pricey.
As for the more urban feel, the suggestions on Stamford and maybe even South Norwalk should do you well.
I would agree with Fairfield as a great call. Good schools and a ton of great shops in the downtown area. You will be very happy with that choice, just not the price perhaps. I would also suggest taking a look at downtown Stratford for a much scaled down version and an up and coming area. There are small resturaunts popping up downtown and a small playhouse tucked away next to the train station. Stratford is reasonably priced with a variety of housing choices from the historic to the contemporary and everyone of my realtor friends are saying that it is the town to watch as it is only improving. And it is on the water. Teardowns are starting to happen as well which occured in Fairfield to the max a few years ago.
Stamford is a good choice as it brings a small city feel with plenty of options. The old say of location goes a long way in CT though...the closer to NYC the more expensive.
Good Luck and have fun with it!
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