Anonymous wrote:

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Anonymous wrote:Kailua, outside of Honolulu.

Most of my family lives in Honolulu (gosh I like typing that word) but if I ever move back it will be to Kailua. Bike-able everywhere.

Born and raised in Honolulu. Kailua is pretty, but the architecture is very hit-or-miss. If you want nice homes and the water, Diamond Head or Portlock are much nicer than Kailua.

I am not thinking about rich or impressive. I love the vibe of Kailua. Portlock is nasty rich, no vibe. Not bike-able or walk-able to anything. My church (Unity) is on Diamond Head, and my nieces went to La Pietra Hawaii School for Girls on Diamond Head, but I don't find them particularly charming in an "i want to live there" way.

I lived in Waikiki (The Wailana) and Hawaii Kai for 5 years. All in, I love Waikiki the most. But it's not a suburb.

Anonymous wrote:

Anonymous wrote:Kailua, outside of Honolulu.

Most of my family lives in Honolulu (gosh I like typing that word) but if I ever move back it will be to Kailua. Bike-able everywhere.

Born and raised in Honolulu. Kailua is pretty, but the architecture is very hit-or-miss. If you want nice homes and the water, Diamond Head or Portlock are much nicer than Kailua.

Anonymous wrote:Atherton Ca

Stevie Nicks and Lindsay Buckingham!

Anonymous wrote:Cold Spring Harbor, NY

Billy Joel!

My husband grew up in Whitefish Bay, WI and it is quite idyllic. When you are there it is obvious that you are in a suburb of primarily well off professionals but it doesn’t have that “obscene wealth” “completely-out-of-touch” vibe that I always get from places like Riverside CT and Winnetka.

I am also a big fan of the mainline of Philadelphia.

Anonymous wrote:Kailua, outside of Honolulu.

Most of my family lives in Honolulu (gosh I like typing that word) but if I ever move back it will be to Kailua. Bike-able everywhere.

Coral Gables, FL

Bronxville, NY for sure. A little cluster of tudor architecture, all walkable, beautiful

I live in Glenview. It is a different mix of people than Wilmette, Winnerka, Glencoe etc. more diverse and balanced. There are working classes people here and millionaires (HHI). And the schools are excellent. The park districts (welcome to the Chicago burbs) are awesome. Public pools, public parks, public park reserves- unbelievable.
Most importantly- the people are nice. Nice. Like I hope my children will be.

The East Bay. Walnut Creek, Danville, San Ramon.

The problem with the Midwest is that it takes soooo long to get anywhere. Even from Chicago, what is there...Lake Michigan? So many more options within 2-4 hrs in your average east coast town. That’s why I’d always pick an east coast suburb...of course California is paradise too

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Anonymous wrote:CT’s Gold Coast - Greenwich, Darien, Westport, New Canaan

Grew up in Westport. You can add Southport. Redding, Ridgefield, Madison, Weston ....

But not nicer than the Chicago suburbs....

No sorry, but CT beats any midwestern town by far

Why? I'm from Westport and think north shore suburbs of chicago are very similar but more charming and shorter/cheaper commutes into the city.

I'm not from either but have spent time in both and have to say those north shore Chicago suburbs are more charming.

I think Westport is lovely and so is Newton, Mass and so are Carmel, CA and LaJolla (although not really “suburbs”)....but the BEST suburb in All of America is the North Shore of Chicago.

So, no, sadly, CT does not “beat any midwestern town by far.” Not Winnetka.

oh PLEASE. Completely disagree. The Gold Coast of CT is one of the wealthiest places IN THE WORLD. Look it up. CT has an "off the mayflower" feel that can't be replicated by anything else. It's not just a money thing. The history, the abundance of private schools and clubs, the nautical feel, the generations of wall streeters that have made their homes there....sigh..you have to get it.
North shore became affluent AFTER WORLD WAR II for heavens sake....

Um the question was nicest suburb. CTs good coast is richer than Chicago's North Shore. I don't think that is up for debate. But I'd it nicer? I don't think so. CT also doesn't have an abundance of private schools. There are a couple in Greenwich and there's GFA in Westport but none of them are so great. Downtown westport has a giant GAP, some empty storefronts and restoration hardware (or it did the last time I was there). So much for a nautical feel. Chicago's North Shore has lovely beaches too and the town centers are very nice too. History of wall streeters? Not sure why that matters. I also don't think the schools are better in Fairfield County CT.

-Westport native

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Anonymous wrote:CT’s Gold Coast - Greenwich, Darien, Westport, New Canaan

Grew up in Westport. You can add Southport. Redding, Ridgefield, Madison, Weston ....

But not nicer than the Chicago suburbs....

No sorry, but CT beats any midwestern town by far

Why? I'm from Westport and think north shore suburbs of chicago are very similar but more charming and shorter/cheaper commutes into the city.

I'm not from either but have spent time in both and have to say those north shore Chicago suburbs are more charming.

I think Westport is lovely and so is Newton, Mass and so are Carmel, CA and LaJolla (although not really “suburbs”)....but the BEST suburb in All of America is the North Shore of Chicago.

So, no, sadly, CT does not “beat any midwestern town by far.” Not Winnetka.

oh PLEASE. Completely disagree. The Gold Coast of CT is one of the wealthiest places IN THE WORLD. Look it up. CT has an "off the mayflower" feel that can't be replicated by anything else. It's not just a money thing. The history, the abundance of private schools and clubs, the nautical feel, the generations of wall streeters that have made their homes there....sigh..you have to get it.
North shore became affluent AFTER WORLD WAR II for heavens sake....

Anonymous wrote:Wilmette, IL. Gorgeous old homes on tree lined streets (some brick). Cute, cute walkable downtown with a train station to the Chicago loop. (<30 minute commute.) Amazing schools.

If I am remembering correctly, you can stroll to the beach too! It's beautiful

I thought Newton, MA was gorgeous. I also love Bryn Mawr, PA.