[TaraAucoin]

Hi,
My husband and 4 daughters (7, 9, 10, 13), are moving to CT. I will work from home, but will need to go to New York City ocassionally. My husband will work in New Haven. We have it down to these towns because they are decently close to NYC and New Haven. We'll be visiting CT next week, but I appreciate any information you have on these towns. Which would you personally choose?
Thank you!

[Stratford, Ct. Resident]

Originally Posted by TaraAucoin

I will work from home, but will need to go to New York City ocassionally.

How occasionally?

Originally Posted by TaraAucoin

We have it down to these towns because they are decently close to NYC and New Haven. Which would you personally choose?

For most of us, neither one would be a 1st choice. What is your budget?

[kidyankee764]

I'm going to assume budget is not an issue.

If commuting to New Haven and NYC, I'd choose Westport, no question. The commute from Greenwich to New Haven will be tough, especially because you would have to go through both Norwalk and Stamford (assuming you'd be driving), and 95 is very congested. Assuming you'd be driving to New Haven and taking Metro North to Manhattan, Westport is definitely your best bet.

Also, Westport's schools are a notch above Greenwich.

[TaraAucoin]

Originally Posted by Stratford, Ct. Resident

How occasionally?

Every few months maybe, there isn't a date set in stone.



For most of us, neither one would be a 1st choice. What is your budget?

We prefer to keep it under 2.5M but can go up to 3 if nessessary.

[Stylo]

If it's truly "occasionally", then Westport, definitely. Greenwich to New Haven could suck. What does occasionally mean?

Because if it's a couple times a week or less, you might want to consider Fairfield and save some money. Or spend your budget and have an amazing house. It's 5 minutes more on the train, but the real estate savings are significant. Westport is nice, but a bit on the material/vapid side. Fairfield schools will provide a more well-rounded, grounded experience for your kids (less little snobs). I have heard complaints of the shallow competition in Westport schools among kids (my daddy has more than your daddy) and general pressure cooker feel. I personally would prefer Fairfield as a town to live in. I find it less congested too, and IMO Jennings Beach > Compo Beach.

You afford the Southport section of Fairfield that borders Westport. The Southport harbor area is stunningly gorgeous, one of the most beautiful parts of the state and many will agree. If I had your budget and situation, I'd be taking a hard look at that area. Greenfield Hill is another upscale area of Fairfield that's stunningly gorgeous. Not many neighborhoods in Westport have quite that charm these days IMO. Westport does have a lot of good qualities though. Depends on your style, I guess.

[Stratford, Ct. Resident]

Originally Posted by Stylo

If it's truly "occasionally", then Westport, definitely. Greenwich to New Haven could suck. What does occasionally mean?

"Every few months".

OP definitely doesn't need Greenwich or Westport. I'm thinking more along the lines of Madison.

[Stylo]

Oh wow, yeah.

Madison without any shred of a doubt. Could get an amazing home for the money. Life is better in Madison vs. Westport/Greenwich. Trust. It is a fantastic town with top notch schools (without the BS you'll find in Westport schools).

I know someone who is an education veteran and high up in the Madison high school and says it's hands down the best school she's ever worked at. She has nothing but good things to say about it and loves the kids.

Most high earners that work in New Haven live in Madison, Woodbridge, Guilford, along the waterfront in Branford/Milford, etc. Westport wouldn't make sense and Greenwich even less.

[TaraAucoin]

Thank you for the suggestions! We'll look into Madison & Fairfield! Thanks for telling me about how snooty some of Westport's kids can be! I definitely don't want my kids in that atmosphere! We were looking into Westport, because of the beaches. Greenwich because of family. Is Greenwich as pretentious as it's made out to be? My sister in law has said no, but I'd like another opinion.

[Stylo]

Originally Posted by TaraAucoin

Thank you for the suggestions! We'll look into Madison & Fairfield! Thanks for telling me about how snooty some of Westport's kids can be! I definitely don't want my kids in that atmosphere! We were looking into Westport, because of the beaches. Greenwich because of family. Is Greenwich as pretentious as it's made out to be? My sister in law has said no, but I'd like another opinion.

I actually find Greenwich to be more of a mix of snooty and non-snooty than Westport, but neither are nearly as laid back as Madison.

If you don't want your kids around snootiness, but still want top notch schools - you can't beat Madison.

That, and Madison beaches are FAR nicer.

If you have family there, the trip to Greenwich isn't bad from Madison if you avoid rush hour.

Again, Greenwich to New Haven commute would be tough. You'll get a waterfront mansion for your budget in Madison, and a pretty nice bigger house in Greenwich. Huge difference.

This should illustrate the difference in cost:

http://www.realtor.com/realestateand...3_M41490-54500
http://www.realtor.com/realestateand...0_M43553-15378

[TaraAucoin]

Originally Posted by Stylo

I actually find Greenwich to be more of a mix of snooty and non-snooty than Westport, but neither are nearly as laid back as Madison.

If you don't want your kids around snootiness, but still want top notch schools - you can't beat Madison.

That, and Madison beaches are FAR nicer.

If you have family there, the trip to Greenwich isn't bad from Madison if you avoid rush hour.

Again, Greenwich to New Haven commute would be tough. You'll get a waterfront mansion for your budget in Madison, and a pretty nice bigger house in Greenwich. Huge difference.

Thanks for the info...Can you tell me more about Southport?