[candreas]

We are moving from Colts Neck, NJ (quite upscale) to CT. Looking for atleast semi upscale, old money, (not too much snobbery) and really dont know what areas to focus on other than the usual Ridgefield, Wilton, Darian and New Cannan. What about Madison, Norfolk, Old Lyme, Old Saybrooke? My husband has to commute to NYC aswell as RI. But is willing to go thru a bit of commuting nightmare in order to live in a great town to call home. Are there any places upscale in the north? Please help!!

[mikidee28]

Greenwich of course......
you can contact me via mikidee28@hotmail.com (for more info)

[mels]

Norfolk isn't an easy commute to NYC or RI. I would avoid being up that far in Litchfield County. Madison will definitely fit the bill. Parts of Old Saybrook would, but may not be what you are looking for. Old Lyme is nice too, not as blatantly affluent as Madison. Any affluent town will come with its share of snobbery. Out of the towns you listed I find Darien and New Canaan to be the most pretentious. It is a little more laidback east of New Haven.

[skytrekker]

One might try Essex or Chester CT-on the lower CT river-not far from the shoreline. Both charming towns with understated living.

[jeremeyk482]

The further east you go, the less pretentious people are.

I would highly recommend Old Saybrook if you don't mind a 2 hr commute to NYC. You can take Shoreline East to New Haven, then switch to Metro North to GC. Driving might be a nightmare.

Old Saybrook is a pristine shoreline community. Many people here are well-off but do not flaunt it. Fenwick is my favorite section of OS, but the cost to live here is high ($2m and up). It's very secluded and away from everything. It's nothing like the pretentious, uppity towns in Fairfield County, as many residents drive older cars by choice. In OS, people are friendly and will smile and say hello in passing. A woman in Fenwick was holding a tag sale this past weekend - she was 'cleaning out' her 7 bedroom mansion but was incredibly friendly and down to earth. Everything at the sale was "negotiable".

The closer to NY you get, the more snobby people get. Even the 'old money' in Greenwich has a certain attitude that you don't find in other parts of CT. NC, Darien and Westport are very pretentious, as is (dare I say) Ridgefield. I've found folks here to be just as bad as NC.

You may want to check out Easton or Redding - nice, rural towns without the status, close to highways, the beach, shopping, etc. About an hour 15mins commute to NYC. School district is top notch as well, which keep home prices high.

[JayCT]

Originally Posted by jeremeyk482

You may want to check out Easton or Redding - nice, rural towns without the status, close to highways, the beach, shopping, etc. About an hour 15mins commute to NYC. School district is top notch as well, which keep home prices high.

Easton and Redding??? These are both very affluent towns with a lot of status. Also Redding is not near any highway, unless you consider Route 7 through Wilton a highway. Schools are excellent though.

candreas - you indicate that your husband has to go into New York and Rhode Island, but do not say how often to each. If he has to go into New York often and RI occasionally, then you should move closer to New York (west of New Haven). If it is the other way around, then I would consider living east of New Haven.

If you are looking for an upscale "old money" town that is not too snobby, then I would consider Fairfield. It is one of the oldest towns in the state with a lot of beautiful older homes and history. It has excellent schools and great shopping, restaurants and entertainment options. It has wonderful parks and beaches (on Long Island Sound though, not open ocean) and there is a wide variety of housing options from starter apartments to stunning mansions. This gives the town a nice diverse population. Southport is one of the most charming villages in the country and Greenfield Hill is beautiful with its rolling hills and gentleman farms. There are neighborhoods of contemporary split levels, colonials, capes or ranches. Lot sizes range from small (50 by 100) to large (Greenfield Hill has minimum two acre zoning).

Fairfield has been named one the best communities to live in by Money Magazine and Ladies home Journal. There is great access to New York with two train stations. A third station is being constructed. It takes a little over an hour into Manhattan from Fairfield. I am sure you willl like it.

If you want to be closer to Rhode Isand but still have access to New York, Madison would be a good choice. It has great schools and a charming downtown. there is also a train station with commuter trains to New Haven where your husband can catch trains into New York. This can be kind of a long ride though so I would not want to do it every day. The drive to RI from Madison would be a breeze though. Good luck, Jay

[jeremeyk482]

Originally Posted by JayCT

Easton and Redding??? These are both very affluent towns with a lot of status. Also Redding is not near any highway, unless you consider Route 7 through Wilton a highway. Schools are excellent though.

I was comparing Easton and Redding to the other towns the OP mentioned - New Canaan, Darien, etc. Compared to these towns the cost of living in Easton and Redding is much less (the average price of a home being substantially less) but still very upscale. People here are more down to earth than in New Canaan and Darien, but less so than east of New Haven.

Redding is a 10-15 minute drive from the Merritt Parkway and a 15-20 minute drive from 95. Route 7 goes through extreme West Redding, but you can also take other routes to the highway depending on what part of town you live in.

[skytrekker]

Just a note

Sex offenders are something none of us want our children subjected too.
City data provides information on this issue for each town. Each of us has the right to make the appropriate decision to live in which town we want. Lets not bring a political agenda to the forum about this issue. Do not judge a town in a negative light because it may have registered offenders. Relying on social and economic demographics in determining which town or city will have these offenders may prove to be incorrect. Upscale communities may have less of this activity reported. The information is here-please make your own judgments on residing in any particular town Regarding this sensitive issue -and not bring it to the forum,

Thanks for your corporation. Moderator.

[outofCT]

New Canaan is very old money type. I would say Wilton, than Southport section of Fairfield. Ridgefield changed to yuppie. Greenwich is mixed. Stay away from Darien or Westport: flashy and noveau.

[elephant]

I think I might be able to give some advice.... I grew up in Essex. My parents live in Madison. I now live in Redding (all three of which you are considering). We also go to Nantucket (which sort of counts as RI) on the weekends, and my husband commutes to the city everyday.

Sooooo....here is my take. Not much of Fairfield County cannot really be considered "old money" anymore. It is newly minted New York City $$ and there is a lot of it. That is not to say that the old guard still doesn't rule the roost, they do, but the affluent crowd is a mixed bag. (Which is a good thing. Wasps don't dominate quite like they used to in Fairfield County.)
HOWEVER, that said, I think you would really like Redding-"the vermont of fairfield county". It has excellent schools, very rural, more artistic people, and a much more relaxed attitude towards money. It is much more affordable than Darien or New Canaan, and not as socially aggressive. It is, however, not as accessible (which keeps prices and people down). There is no town center, no commerce, no traffic lights.
You will drive 15 minutes for milk. It is the country. Towns "down county" on the coast are much more 21st century (strip malls, I-95 highway, traffic, etc.)

Ok. Madison. Much more affordable than Fairfield County. You will however get quite the snobby attitude there. It is very new money and showy. Think soccer moms/doctor dads. Very cookie-cutter conservative.

Essex is a complete gem. Not to many places on the planet left like it. It is still the old waspy/preppy new england that you either hate or love. (we love and would be there in a heartbeat if my husband didn't have to commute to nyc)
It is charming, charming, charming. Schools not that great however, but housing much more affordable.
Good luck!