[EastcoasterAtHeart]

Hi there! My husband and I are moving to CT from Silicon Valley, CA, with our 20-month old son. I'm originally from Trumbull so know a bit about these towns but was hoping to get some more feedback. My husband will be commuting to Chelsea in NYC approx. 2-3 days per week and I'll be driving to Trumbull frequently. We have narrowed down our search to: Greenwich, Darien, New Canaan and Westport. We can spend up to $1.75m on a home. Our favorite town is Westport but it is also the furthest commute. Does anyone know how bad the commute to Chelsea would be? Of the other three towns, which is the most like Westport? We love the idea of good public schools, a downtown section (does Darien have this?), liberal views (maybe Westport is the only one that fits this bill?). Any feedback, opinions, advice would be greatly appreciated. Thank you in advance!

[skytrekker]

Darien is the most conservative town, I do not feel if you are San Francisco bay area liberal you would really feel comfortable there. New Canaan is also not really a liberal bastion. Westport is perhaps the best choice if you are looking for views that are leftist liberal/progressive.

Greenwich is fairly liberal socially, but tends to be old money conservative.

[JayCT]

EastcoasterAtHeart - All of the towns mentioned are excellent places to live and raise a family. The schools are all excellent and there is a large variety of family activities. All of these towns have the traditional downtown area like Westport. These are mostly surrounding the local train station.

You should note that the difference in commute time between Westport and Greenwich though is not as much as you would think. The trip from Greenwich to Grand central is 45 to 50 minutes. From Westport it is 60 to 65. There is however a big difference in housing prices with Greenwich being the pricest. $1.5 million in Greenwich will buy you a modest home. in Westport, it would be a bit nicer. Also as you know Westport is closer to Trumbull and that will reduce the time you need to travel on the highway to get to family.

Basically, if you like Westport, then by all means look in Westport. The added travel time for the 2 or 4 days a week would be minimal and you will most likely be able to afford a nicer home. Hope this helps, Jay

[kidyankee764]

I agree that you should check out Westport. I think New Canaan is actually the furthest but that depends on what part of town you're from. As for good schools, you have nothing to worry about in the suburban Fairfield County towns. They are among the best districts in the nation.

Greenwich is a very big town, and with it comes plenty of status. It never used to be that way, but walking downtown on The Ave I feel like I am in Beverly Hills instead of Connecticut - it can be quite pretentious. Home prices will be a lot, but commute time will be less. It's an excellent town to raise a family and is close to nearly anything you could want.

New Canaan is a very nice, spread out town. There is a little town center but generally you will have to travel out of town for some of your needs. Norwalk and Stamford are right next door though.

Darien is a nice town, but expensive and very wealthy. You will not get a lot for your money here, and it's very, very conservative (fiscally rather than socially). I believe there are many Bush fans though!

Westport seems exactly what you're looking for. The town can be a bit flashy but the schools are excellent and there is plenty to do in town. I have always loved Westport - I lived there for a bit when I was younger. And as jay said, you can get a little more house for your money as opposed to Darien, New Canaan and Greenwich.

Anywhere in CT will be more liberal than the south, midwest and even parts of socal.

[Viralmd]

How about checking New Jersey? The commute to Chelsea will require getting over to the West Side and then downtown. The commute from NJ would leave you part way there: on the West Side.

[EastcoasterAtHeart]

Thanks to everyone for the replies. They are much appreciated. Viralmd, all of our family is in CT so although NJ would make the most sense for the commute, free babysitting wins out in the end!

[Stratford, Ct. Resident]

Originally Posted by kidyankee764

Darien is a nice town, but expensive and very wealthy. I believe there are many Bush fans though!

Interestingly enough, Darien's Board of Selectmen is now a Democratic majority. Perhaps there's hope for the town, afterall. LOL.

[bsri]

Hello, I live in New Canaan and used to commute to West 21st St in Chelsea. We moved to CT from Seattle so we went through the same decision process. It's exactly 50 minutes by car during non-rush hour...take the Merritt and make your way down the Westside Hwy. New Canaan is fantastic. It's quiet and unlike the other 3 towns mentioned, does not have I-95 cutting through the town; the other 3 get the beaches however. The downtown in New Canaan is beautiful and it is a great place to raise kids as are all of the towns. In terms of liberal politics, all 4 towns are made up of educated and wealthy people. You are going to get a cross-section of political views. People contribute to both sides of the aisle: If it is really important to you, you should look at the contributions at the Federal Election Commission (link provided.) Westport is more liberal, the other 3 are fairly similar. You really can't go wrong with any town. However, my wife and I fell in love with New Canaan the first time we drove through it. New England feel with easy access to NYC.

Presidential Campaign Finance

[maddleo]

I have been in all of these towns as a worker so may not know enough of the details that could help. Actually, they are all nice,upscale suburban areas that are highly rated as part of CT's "gold coast" The school system in them are all good but I would give Greenwich the edge based on what I have read and heard. It is also the nearest town to NYC with great commute on the Metro North train that leaves from Greenwich station. It is just about 20-30mins, and a great ride. I would not plan on driving into the City as that could be a great hassle. If it were my choice to make I would make it for Greenwich or Darien only because these are on the direct trail line while for New Canaan you have to make a connection, but they are all nice towns, each with their Downtown area not unlike most upscale suburban towns.

[skaneatelesmom]

I grew up in Greenwich but chose to raise my family in Darien. Two very different towns due to size. Darien still has a small town feel whereas Greenwich feels more like a small city. I think Darien has a better sense of community because of that.
But, as others have said, both are outstanding choices. If you would like names of great realtors in either town (sorry, don't know anyone in Westport or NC), send me a private message and I'll be happy to help.
Joanne