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I have the same issue -- we love the look of downtown Westport but I think we would be more comfortable in Fairfield. We are looking in the beach (Penfield, I guess) area near Sherman Elementary school. Pretty sure we're going to pull the trigger. Thanks to all for your advice.
This has been debated on this board before and I believe that Fairfield being located next to Bridgeport is not a problem. First of all, like any major city Bridgeport has its good areas and its bad. All of the neighborhoods along the Fairfield side of the city (Black Rock, Brooklawn and the North End) are very good. I fact many times you would not even know you have left Fairfield and entered Bridgeport when driving around the area. once I was driving out-fo-town friends around and they remarked how beautiful Fairfield was. They were shocked when I told them we were in Bridgeport. Jay
I agree that Bridgeport has beautiful areas and is a nice town with good potential. I think it's good for people to be educated on what city lies next door. The majority of people could care less. But I think Bridgeport is either a diamond in the rough or a huge problem about to get worse. Hopefully it will only get better. As to whether or not this affects house values in Fairfield, I doubt--but it could if Bridgeport continued to go down the tubes.
There are plans to construct a 10 foot high wall along the border of Bridgeport and Fairfield that will only allow those Bridgeport residents working as domestic help to enter Fairfield or Westport. Everyone else from Bridgeport will be banned from sharing in the "fabulousness" of Fairfield County.
I'm just tellin' it like it is. I like Bridgeport. It is Fairfield County's worst city, by far though. That's just the truth. I have faith it will change, but now it would not be a top choice if living in Fairfield County.
With the price range you are looking at and concetrating on Fairfield you will be able to do very well. Southport would be a home run but near Penfield, Jennings or South Pine Creek Beaches you would be very pleased. You may want to look in Greenfield Hills if you don't mind a larger yard and house, but also it would be a drive to almost anything and less interaction with the neighbors.
What western suburb are you moving from? Fairfield County gives you more bang for your buck in regards to lot sizes, but the finishes in some of the homes are of overall lesser quality then the western suburbs of Chicago. Most of Fairfield County would remind you of Lake Forest or Glencoe in Chicago. It's not nearly as dense as Hinsdale or Glen Ellyn if that gives you a good idea.
I think you might like Weston or Wilton, New Canaan is nice, but more expensive.
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