Define what it is you want
Dear CollegeGuy987,
Several weeks back, you sent me a message based on comments I made about Bedford (the town where I live). I've seen that you're asking about living in a few different towns, and that you're concerned about some lifestyle issues, local culture, safety and racism.
I hope that through the responses you've gotten on these various threads, you've come to a clearer understanding of the fact that all of these areas that you've been asking about are "safe". Also, as regards racism: Frankly, in these uber-rich towns, if you can afford to live there, you are welcome whatever your skin color or heritage. (BTW: I've lived in Bedford for half of my life, and for ten of these years a black family lived next door. I never asked them, but I don't think they experienced any racism. I have friends who are a inter-racial couple. They lived in a very nice area of Mount Kisco, and if they ever felt uncomfortable anywhere around here, I'm not aware of it.)
Yes, there are some exclusive clubs that discriminate against anyone who is not exactly their memberships' profile, and that can have to do with religion, nationality, economic status -- or race. That is going to be true ANYWHERE there is wealth. A-N-Y-W-H-E-R-E.
You've made it clear that you can afford this turf. In my opinion, what you need to do is be honest with yourself and do some heavy, introspective thinking. Do you relish having the "bragging rights" of living in Greenwich or Bedford? (That's OK if you do. That's what keeps the real estate prices where they are. If that is something you want, it will simplify your search A LOT if you are honest with yourself about it.) Or is it really important to you to have a more "live and let live", easy going community? There are some really wealthy communities like that too. Katonah is one. Also ask yourself how much interaction you're really going to have with your community. If the answer is "next to none", then you should consider factors such as the physical beauty of one place versus another, its geographical location as regards things like the convenience of getting to NYC, and not to be forgotten, issues such as whether building an estate in one location or another is a good business decision (looked at purely as a real estate investment).
These are the sort of questions I think you ought to be asking. So far, based on the posts you've made on this site, I think you've been approaching this thing all wrong.
Good luck,
MsAlex
PS: You can drive fancy ultra-expensive cars anywhere around here, and you will not be alone in driving such cars either.
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