Anonymous wrote:I regularly work in most of the towns listened in this thread. I’m a general contractor-remodeler and all the towns have their own vibes.

You mention that you in Rye and Darien. Both lovely, scenic towns with a strong beach vibes. As much as I love the drive through Darien and Rowayton I would not be comfortable living there. Invariably I have problems with my clients and getting paid and I always get the vibe that the wives are under a lot of pressure to keep costs in line. Finance doesn’t pay what it once did and the pressure for show is pretty intense so the Lax Bro husbands are feeling the pain. Yes, it is ok if you sense my disdain.

We say the folks in Darien wish they lived in Greenwich but they don’t have the money. Both demanding clients but at least the folks in Greenwich have the money to pay to be demanding.

Personally, Darien would be way too strung out for me. I have had good luck with clients in New Canaan and for what was once one of the richest towns in the US you can get screaming buys. If you are not tied to a NYC commute you can go as far north as Ridgefield. Beautiful town real estate is very reasonable but taxes are relatively high. Would definitely make my short list as you will experience down socio-economic diversity in a very pretty town.

This is an anonymous board so I will say it. When I think of Darien and Rye they are very WASPy. When I think of Chappaqua I think Jewish. Some stereotypes have a basis in truth. And while I am not Jewish I have a lot of family in Chappaqua - actually Millwood and they are not my cup of tea. Way too impressed with themselves and they ain’t all that.

Very good values in the River towns but very different vibe from Rye and Darien. Both are old WASPy money - kids go to SLACs and play Lacrosse and then go into the family business - Wall Street. That’s not the River towns.

Westport is nice but has changed a lot in the past and all my friends that live there want to move. And 2M isn’t going to buy you much.

I also like Old Greenwich - smaller, nice older homes. Some big dollar ones on the water. Very nice family feel.

Further up the line is Southport - incredible harbor and antique homes. Beautiful - property taxes will kill you and if you didn’t come over on the Mayflower well you may not fit in. and 2M is likely not a big enough buy in.

That all said I love the feel of CT and glad that I raised my kids here. It’s not perfect but definitely feels like you won life’s lotto living here. You just have to work hard to find your tribe.

Anonymous wrote:Cold Spring/Garrison is lovely and has the small community vibe.

Croton on Hudson also, if you want to be the "multi-millionaire next door" type and still have +/- 1 hr access to the city.

Anonymous wrote:

Anonymous wrote:I definitely wouldn’t do someplace like chappaqua if you’re not going to use the public schools. What about someplace like beacon? Too far?

Beacon is in Duchess County.

Anonymous wrote:I definitely wouldn’t do someplace like chappaqua if you’re not going to use the public schools. What about someplace like beacon? Too far?