People aren't buying the iconic, sprawling mansions in one of America's richest cities, a haven for Wall Street types an hour from NYC. I spent a day there — here's what it was like.

Katie Warren/Business InsiderGreenwich, Connecticut, has for years been known as a wealthy enclave.

On an unseasonably cold March morning, I got on the Metro North from Grand Central Terminal in New York. My destination: Greenwich, a town on Connecticut’s coast about an hour from the city.

Greenwich is consistently ranked as one of the richest towns in America. In 2018, the average household income in its Old Greenwich neighbourhood was $US336,692, the 12th highest in the nation, according to Bloomberg.

The year before, two Greenwich ZIP codes – 06878 in Riverside and 06831 in Greenwich – ranked among the wealthiest in the US.

It’s been known as a wealthy enclave for years.

“For more than a century, Greenwich, Connecticut, has attracted some of the biggest, newest, shiniest fortunes in America,” Nina Munk wrote in Vanity Fair in 2006. “Today that money comes from the trillion-dollar hedge-fund business, which occupies a third of the town’s office space, and whose managers are behind a decade of over-the-top real-estate deals, teardowns, and mega-mansions.”

But people are no longer buying Greenwich’s iconic mansions at the same rate they used to, Bloomberg reported. Buyers are moving more toward smaller condos, leaving many larger homes sitting on the market. Single-family home sales dropped 25% in the first quarter of 2019, according to Bloomberg.

Greenwich’s “hedge fund capital” nickname is well-earned: The city is also home to hedge funds including AQR Capital Management, Viking Global Investors, K7 Investments, and Axiom Investors.

Robin Kencel, a real-estate broker at Compass and one of the founding agents of the Greenwich office, said that about half of her buyers work in finance.

“The others are entrepreneurs, they work for corporations, they’re in the entertainment business,” Kencel told me. “Finance is still very important to Greenwich, but I think you’ll find it’s much more diversified in terms of occupations than when people were first coming out in the turn of the century and the trains came out and it was the summer homes for finance folks.”

Kencel said she gets about 45% of her sales from Manhattan. Buyers from the city are “always surprised how quick it is to get here,” she said.

I took the train out to Greenwich for a day to get a feel for the affluent community. Here’s what it was like.


My day began at Grand Central Terminal in New York City.

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I got on a Metro North train toward Stamford, Connecticut, which would stop in Greenwich in under an hour. The train was fairly empty, but I imagined the train from Greenwich to New York City at the same time of day would be full of people commuting into the city.

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My peaceful train ride lasted a little less than an hour. I got off the train at the Greenwich station.

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One of the first things I saw after getting off the train was the headquarters of AQR Capital Management, a hedge fund that has about $US196 billion in assets under management. Greenwich is home to several hedge funds, earning it the nickname “hedge fund capital.”

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Source: AQR


After stepping out of the train station, I soon passed a car dealership selling Rolls-Royces …

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… and a neighbouring Lexus dealership.

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It seemed that most any car on the street was either a Mercedes, a BMW, an Audi, a Lexus, or a Range Rover.

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I started making my way toward Belle Haven, an exclusive gated neighbourhood that used to be a resort community for summer vacationers from New York City. Belle Haven has been home to some prominent people over the years, including the hedge fund mogul Paul Tudor Jones, the singer Diana Ross, and the businessman George Skakel.

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Source: Greenwich Time


The very first house I saw had a sign indicating it was equipped with a home security system. As I walked through the neighbourhood, I saw that was the norm. The streets were quiet and lined with trees.

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Some of the homes were on smaller lots …

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… while others sat on large swaths of land.

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The houses seemed to get progressively larger the farther I walked into Belle Haven.

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Shelly Tretter Lynch, a real-estate broker at Compass in Greenwich, said her average home sales in Greenwich were between $US4 million and $US10 million.

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I was surprised to come across a luxury hotel in the residential neighbourhood. The Homestead Inn has a top-rated restaurant by the chef Thomas Henkelmann.

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Source: Greenwich Time


The hotel’s rates range from about $US280 to $US495 per night, according to its website.

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Source: Homestead Inn


As I continued my walk, I noticed that many of the neighbourhood’s homes were set well back from the road and protected by gates.

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Others were hidden from view behind tall hedges.

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Many of the homes I saw seemed quite old, but they were very well maintained.

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I headed toward Belle Haven Club, the neighbourhood’s waterfront country club.

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But when I made it to the club, I found I couldn’t get a clear view through the hedges and fences.

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The members-only club is apparently not quite as exclusive as it used to be.

“As long as you’re a citizen in good standing and you have friends in the area, it doesn’t seem to be an issue getting into the club,” Debbi-Lyn Trager, a local real-estate agent, told Greenwich Time in 2015.


With my attempt to get a peek at the country club thwarted, I took an Uber back to Greenwich’s downtown area, with a plan to walk up Greenwich Avenue, the town’s commercial center. The street had a charming and historic small-town feel.

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But the shopping options were anything but quaint. One of the first stores I spotted was Theory, which sells $US600 blazers, $US285 pants, and leather jackets for upward of $US1,000.

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Source: Nordstrom


As I strolled up the street, I spotted someone wearing the Orolay coat from Amazon, the parka that’s said to have originated with Upper East Side mums and went on to take over New York City. I’d go on to see three or four more people wearing it in Greenwich.

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Source: Business Insider


Greenwich has its own Apple Store, right next to the upscale menswear retailer Rodd & Gunn.

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All the shops on the avenue, from Athleta to Warby Parker, looked almost brand-new.

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I passed by darkened windows of a former Tesla dealership, with a sign in the window saying all sales are now online.

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Many of the cars parked on Greenwich Avenue had licence plates from New York and New Jersey. I couldn’t help but notice how clean the footpaths and streets were — usually a mark of an affluent community, I’ve found.

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The luxury French retailer Hermès has a spot on Greenwich Ave.

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There’s also an impressive-looking Tiffany & Co. …

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… and a Saks Fifth Avenue, the luxury department store whose flagship is in New York City.

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Source: Saks Fifth Avenue


I stopped at the local Starbucks for coffee. It seemed to be a go-to spot for informal business meetings.

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It was there that I spotted the first person wearing a Canada Goose parka — which can cost up to $US1,600 — though I’d go on to see several more throughout the day.

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Source: Canada Goose


Just a block or so from Greenwich Avenue are some hedge fund headquarters, including that of K7 Investments …

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… and Axiom Investors. Robin Kencel, a real-estate broker at Compass in Greenwich, said that about 50% of her homebuyers work in finance. Ray Dalio, the founder of Bridgewater Associates, is one of the town’s most prominent residents.

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Source: Stamford Advocate


After my tour of Greenwich’s compact shopping center, I started walking up West Putnam Avenue.

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I passed a Whole Foods Market, which, of course, had several Mercedes cars in the parking lot.

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Earlier this year, Greenwich was ranked the safest town in America by the home security company SafeHome.org.

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Source: Patch


I started heading away from the town center to another residential area, the Putnam Hill Historic District, which was once the center of Greenwich.

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Source: Greenwich History


Like in Belle Haven, the streets were extremely quiet and filled with large, beautiful homes.

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It was a weekday afternoon, and I saw very few people walking around, apart from one older couple with a dog.

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My next stop was Round Hill, an area north of town where you can apparently find sprawling countryside mansions. Out here, the homes were indeed noticeably huge and set on large pieces of land.

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Source: Stanton House Inn


Some were set back at the end of long driveways marked by ornate gates. A few had intercom systems right outside.

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Peeking through one gate, I got a glimpse of Round Hill Manor, one of Greenwich’s great estates, according to Sotheby’s International Realty. It’s on the market for $US22.5 million.

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Source: Sotheby’s


Greenwich is consistently ranked as one of the richest towns in America. In 2018, the average household income in its Old Greenwich neighbourhood was $US336,692, the 12th highest in the nation.

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Source: Bloomberg


Kencel told me that 45% of her home buyers come from Manhattan and that more and more wealthy city dwellers are choosing Greenwich for a vacation home. “People who might be looking in the Hamptons for summer residences are now realising Greenwich is just 45 minutes from the city,” she said, adding that Greenwich has four beaches.

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As I headed back to Greenwich’s train station for the journey back to New York City, I definitely understood why wealthy Wall Street types and so many others are drawn to the town; after all, it’s a quiet, clean, and safe place to live — if, of course, you can afford the price tag.

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