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Jay, I'm very familiar with Greenwich. As I have said, of course there's old money there! There is old money in most places where there is money, at least on the East Coast. The issue about the nature of the place overall. For example, while Greenwich has distinctly middle-class sections, it is not, overall, a middle-class town in character. Similarly, while I know a number of WASPs who live in Westport, most people would not say that Westport is predominantly a WASPy town. So while there are surely old-money people in Greenwich, to me, in my experiences, it is a town that today is largely dominated by a new-money culture. This is admittedly an opinion.
I think of Greenwich as a city because of its large population (roughly 60k), large public schools, and its core, which today includes the headquarters of a number of large firms and office buildings. Whether it is or is not is debatable, I suppose. But compared to the other peer towns mentioned here (Darien, New Canaan, etc.), it's much more city-like, in my opinion.
This is probably not particularly relevant to OP. It seems like Greenwich is probably the best option for her if she chooses to move. Particularly because of its tax rates.
As a family of 4, I would say that a salary upwards of $250K in both Fairfield and Westchester counties would most certainly lessen financial constraints. Coming from the midwest, I would agree that there is such an abundance of wealth in both counties that is very mind boggling at times. Yet we have adjusted very well in part that there are many neighborhood pockets that are very middle class in character, and fortunate enough to have met other families from other 'wealthy' towns that are very down to earth regardless of their financial status.
One suggestion that recently was given to us was to consider an updated condo in Chappaqua in the $500K range with taxes under $10K. In hindsight that would certainly been a reasonable alternative to a SFH 2 yrs ago, had we been aware of it. Just so we can look into it further, what neighborhoods of Greenwich are more down to earth?
One suggestion that recently was given to us was to consider an updated condo in Chappaqua in the $500K range with taxes under $10K.
Don't forget about common charges with condos. It isn't all that uncommon to see the cumulative total of tax and C.C.'s on a 3BR. condo meet or exceed the real estate tax on a comparably sized single-family house.
The most affordable neighborhoods in Greenwich are Byram, Glenville, Cos Cob and North Mianus -- Byram being the most affordable. Please be aware though, that while Greenwich would be the CT town most convenient to the city, it would be a long commute to Chappaqua. I'm not sure how you'd get there, but there isn't a direct route that I can think of...
The northwest corner of Greenwich is only about 4-5 miles from Chappaqua . King St.( I forget the Rt. number -possibly 120A ? ) will take you right into Chappaqua center from Greenwich.
From Byram or Glenville it's easy to pick up King St. From Cos Cob & North Mianus more difficult a drive. North Mianus maybe the Merritt to King St. For Cos Cob, can't think of a good way without either going up to the Merritt or west on Rt 1. to pick up King St. Cos Cob would be the longest drive.
The northwest corner of Greenwich is only about 4-5 miles from Chappaqua . King St.( I forget the Rt. number -possibly 120A ? ) will take you right into Chappaqua center from Greenwich.
From Byram or Glenville it's easy to pick up King St. From Cos Cob & North Mianus more difficult a drive. North Mianus maybe the Merritt to King St. For Cos Cob, can't think of a good way without either going up to the Merritt or west on Rt 1. to pick up King St. Cos Cob would be the longest drive.
The problem with that, is if you live in the eastern side of town (ie Riverside or Old Greenwich) you are 20-25 minutes from King St. Greenwich is big and spread out. If you had to commute to Chappaqua, I'd stick to looking in Byram and Glenville.
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