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1. Pound Ridge, NY
Pound Ridge, NY is located in northern westchester, and is one of the richest towns in westchester. Drive around Pound Ridge, and try to find the "less nice," or poor part - you won't find it because we don't have one. Its hard to find a house under a million dollars. And if you think the houses in Beverly Hills are expensive, they're the same prices (or more) in Pound Ridge. People who go to public school, attend Fox Lane High School. People from Pound Ridge consider Fox Lane ghetto, only because in elementry school we had 2 black people and 1 spanish person - but our high school is very diverse. Although most people are well off, Pound Ridge is much less status oriented then neighboring towns like Bedford or New Cannan.

Pound Ridge is home to many celebrities and city weekenders.
Pound Ridge, NY is Home of the celebrites of Mike Meyers, Christopher Reeve, Tom Brokaw, Vera Wang, Susan Sarandon, Tim Robins, Richard Gere and more
2. Fairfield County
One of the U.S.'s most afluent counties which is located in Southwestern Connecticut bordering westchester county, across the long Island Sound it borders on Long Island. It contains many wealthy people including the Sachs from Goldman Sachs, Gene Wilder, Martha Stewart, and the list is extremely long. It contains Bridgeport which is where all the minorities live and has actually improved financially over the past few years as has norwalk. Contrary to popular belief Stamford IS ALSO a very wealthy city except for its southern district. Stamford cotains area code 06903 which borders Bedford and Pound Ridge NY, Greenwich, and New Canaan. This area code is the most afluent in the area.
You only wish you could live in Fairfield County.
by Jake S Jun 3, 2005 add a video
3. Tewksbury
Very wealthy town in Hunterdon County, NJ. Has a very small village area at "Oldwick". Very quaint and rural. James Gandolfini (Tony Soprano) just bought a house here in the past year. 87% white, but of course all the Indians and East Asians will change that fast as they are continuing their onslought into many of the historical colonial 200 - 300 year old towns in NJ. Nonetheless, this town is a very ideal place to live with outstanding schools. Very similiar to Pound Ridge, NY.
Resident 1: Yo I heard Tony Soprano just moved to Tewksbury with his Asian wife.

Resident 2: Yeah, he wants a more private town to live in as he values his solitude as his Asian Geisha doesn't give him any back talk like dem' loud mouthed American ho's.

Resident 1: I think you just told way more than I wanted to hear. No relax and let's hot box some chronic blaze in my new Beemer, my daddy just bought me.

Resident 2, 30 minutes later: " I think I'm Kung Fu fighting" Du da du da du da doot doot fighting"
4. Westchester
The richest county in Ny State, that directly borders NYC to the north, and borders CT as well. Counties north from Westchester like Putnam, Dutchess and Ulster are EXTREMELY different from Westchester. Westchester pretty much owns LI.

The Breakdown.

Westchester is actually not a completely rich county. It has more racially diverse areas like Mt. Vernon, New Rochelle and Ossining and Yonkers. Yet there are extremely rich towns like Scarsdale, Armonk, Rye, Bronxville, Larchmont and Bedford which give Westchester its rich reputation.

Rich and Preppy
Scarsdale - quite possibly the most annoying town in Westchester as everyone there works in NYC and sends there kids to Scarsdale HS, which happens to have a great education. The old country-club town. Like a Greenwich of Westchester.
Larchmont - same as above as it borders scarsdale
Rye and Bronxville - Full of annoying stuck up rich kids who think they are ghetto.

Rich Towns in Southern Westchester
Pelham - a town w/ kids who think they are ghetto cause they live near Mt. Vernon and NYC.
Harrison - everyone there is rich although there are some actual middle class residents.

Northern Westchester
Bedford - Very rich town with a diverse HS with kids from Mt. Kisco, Bedford Hills, Pound Ridge, and Bedford.
Pound Ridge - nothing wrong here. old country town with nothing in it.
Mt. Kisco - called a "rough" town in N. Westchester but its nothing like that. The only town in the area with an actual t...
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