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This guy I'm talking about is:
-late 20s
-professional (salary is far in six figures)
-single individual
-loves the circa 60 fahrenheit temp at times, loves when it rains heavily at times, likes the snow, loves when it gets cold in the winter
-wants to live in an affluent leafy neighbourhood (not the mile long driveway, gate types, think palo alto, but generally not AS expensive as Palo Alto)
-wants to live near a golf course, a sports club, high scale fitness venues
-wants to live not far from amazing shopping
-wants to be near great bars, great restaurants
-loves hunting in abundant fields of deer and/or elk, skiing, surfing: doesn't mind driving a few hours to get to these places!
-doesn't mind extreme weathers
What area in America, best reminds you of this list above.
Sounds like the Northeast to me, somewhere in or around Boston or NYC. The surfing won't rival Southern California, but it is possible in the Atlantic, and these two metros tick off everything else on your list.
And it's nice to find somebody who doesn't faint at the thought of living someplace where it snows.
This sounds very much like the DC area, specifically Northern Arlington. But I think you would like Bethesda, MD/Chevy Chase, MD west of Rock Creek Park neighborhoods in DC. Surfing is good in Virginia Beach if you don't mind travelling down that way. Hunting is good in West Virginia, or in Virginia. 6 months are in the mild weather zone, plus 4 months summer, 2 months winter.
I would suggest Boston as well. Frankly the entire BoshWash corridor you will find places you like. Basically this sounds like the East Coast would fit you very well. NY, Philly, DC, and Boston all have places which will fit your criteria.
I agree with northeast or maybe washington state/northwest areas.
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