Choose Your Gold Coast: A House Hunter’s Guide to the Filets

Manhattan: Fifth Avenue

The draw: The ancient Greeks idealized their women as statuary, but the closest thing New Yorkers have is real estate. Fifth Ave. is the ultimate social X-ray, Truman Capote’s “swan” made stone, with feet in Washington Square and fingertips stretching into the million-dollar brownstones of Harlem. Billionaires stud her slender torso like diamond buttons. Her shopping district has the economy of a mid-sized European country. Mighty battles are fought to live with her on Central Park, where mansions have been replaced with mansions stacked on mansions. In the crowded pantheon of Manhattan real estate gods, Fifth Ave. is regal Athena, with Jackie-O sunglasses and a Hermés scarf, knotted just-so.

Who lives there: Is it possible to be born on fifth base? Yes, for the families who call this storied boulevard home. And they keep coming: in March, Rolling Stone Keith Richards paid $10.5 million for a penthouse at 1 Fifth Ave. Rupert Murdoch set a then-record in 2005 when he paid $44 million for a Rockefeller family triplex at 834, it has since gone to his soon-to-be ex-wife, Wendi. This June, Edgar Bronfman Sr.’s penthouse aerie at 960 set a co-op record, going to Egypt’s richest man for $70 million. That bar has since been raised by $1 million.

Neighborhood hangout: Doubles, a private club downstairs at the Sherry-Netherland, 783 Fifth Ave., is an intimate space where plutocrats can relax with their wives. (Plutocrat wives-in-waiting hangout next door, at the bar at Harry Cipriani.)

Local indulgence: A $2 hotdog from the cart at 59th and Fifth. Because when you own the universe, sometimes you just want a moment of normality.

Manhattan: The High Line

The draw: Just a decade ago, West Chelsea was a badland of taxi garages, derelict warehouses and the kind of nightclubs that don’t like witnesses. Priced out of Soho, downtown galleries have now transformed those spaces into the heart of the city’s multi-billion-dollar art market. The addition of the High Line elevated park has turned the quarter into a magnet for ambitious residential architects, art collectors and billionaire scene-makers. Say hi to Barry Diller and Diane Von Furstenberg if you run into them on the street—they throw great parties.

Who lives there: GLG hedgefund manager Pierre Lagrange paid $11.3 million for the penthouse at HL23, architect Neil Denari’s show-stopping High Line condo building that has been reviewed by everyone from the Times to Kanye West (he called it “real dope”).

Mr. Lagrange, a benefactor of London’s Tate Modern, is famous for his postwar and contemporary art collection. He is also famous for having what is believed to be the most costly divorce in British history ($260 million.) After dispatching Mrs. Lagrange, he took up with male fashion designer, Roubi L’Roubi, and bought him Huntsman—the venerable Savile Row tailor who has dressed everyone from Winston Churchill to the Earl of Grantham on Downton Abbey.

Neighborhood hangout: Morimoto for the omakase or a discreet back table at Bottino, the Italian restaurant-cum-art-world-cafeteria, to clinch the deal on a Richard Prince.

Local indulgence: A million-dollar Cecily Brown from the nearby Gagosian Gallery.

Saddle River, New Jersey

The draw: Jersey? Sure! New York City’s triple-tag-team tax structure (city, state and federal) make Bergen County an attractive option for wealthy families who’d like to give their kids, and their money, some space to breathe. Saddle River is only 45 minutes from Midtown. But its mellow, wooded hills make it the perfect setting for your money manager’s faux-chateau, complete with a pool house and six-car gaage.

Who lives there: Just this January, Rosie O’Donnell dropped $6.375 million on a “gated, French Country estate” built in 1928. Author Mary Higgins Clark, old-school rapper Reverend Run, and fund manager Stuart Zimmerman are other prominent locals. Former hedge funder James Nicholson, now a guest of the state, was arrested in his Saddle River chateau in 2009, before being convicted of running a $140 million Ponzi scheme. His six-bedroom French-style manse later sold at the fire-sale price of $4.6 million.

Neighborhood hangout: The Saddle River Inn serves French cuisine in a historic barn. Locals are divided on whether new ownership has improved this storied restaurant, but it’s still a hub for neighbors and visiting grandees, like Gov. Christie.

Local indulgence: For the fountain in your formal grounds: a dozen imported Japanese koi (at $265 each) from local water lily farm, Waterford Gardens. (Slogan: “Keeping ponds real.”)

Greenwich, Connecticut

The draw: This is where hedge funders keep their hedges. If Lewis Carroll had written about real estate, he might have invented Greenwich, with its fantasy landscape of English stately homes that includes Georgian mansions, some castles, Tudor-revival and even actual Tudor, in the form of a 16th century manor, imported stone-by-stone from Britain. In April of this year, waterfront Copper Beech Farm (and its 50 acres) became the most expensive house in the country, when it sold for $120m. There’s a reason why Greenwich is the only place whose workers choose to commute in from Manhattan—housing is cheaper here.

Who lives there: Forbes names 10 billionaires who reside in Greenwich, from Bridgewater Associates founder Ray Dalio ($14.4 billion) to chokehold mogul Vince McMahon ($1.2 billion). SAC Capital’s Steve Cohen is valued at $11 billion, but his $23 million, 35,000-square-foot house is worth considerably less than the estimated hundreds-of-millions’ worth of artwork inside. Hedge funder Paul Tudor Jones II ($4.3 billion) is locally famous for the holiday light show he puts on at his estate, synchronized to music on a local radio station.

Neighborhood hangout: Davos.

Local indulgence: Insider trading.

Westchester: Bedford, Bedford Hills, Chappaqua, Pound Ridge

The draw: If the Hamptons is like Prince Harry, then Westchester is Prince William. One’s a sexy idiot who parties a lot and gets all the press, but the other holds the real power. Seat of Clintons, Cuomos, Oscar-winners and Wall Street tycoons, this quiet county is home to the country retreats of the men and women who run New York.

Who lives there: Bill and Hillary Clinton brought (unwanted) international attention to the county when they paid $1.7 million for a Chappaqua house in 1999. It’s no wonder Ms. Clinton later said she felt “dead broke,” when area homes—like the modernist Twin Ponds in Bedford Hills—can list for $30 million. Fatal Attraction was partly set in Bedford, where both Glenn Close and Michael Douglas have homes for real. (Mr. Douglas and wife, Catherine Zeta-Jones, recently listed their estate for $8.1 million.) Music mogul Clive Davis hosts industry retreats at his home in Pound Ridge, where he stages a private karaoke contest for the likes of Aretha Franklin called “Pound Ridge Idol.” Hollywood “it couple” Ryan Reynolds and Blake Lively are also the proud parents of a $5.7 million Pound Ridge estate.

Neighborhood hangout: Crabtree’s Kittle House in Chappaqua, a restaurant and inn partly inhabiting a 1790 barn, attracts the area’s A+ list. We imagine the powder room is where Ms. Clinton and Blake Lively swap Oscar buzz and foreign policy gossip.

Local indulgence: Plotting the takeover of government/Hollywood/world financial markets.

DUMBO & Brooklyn Heights, Brooklyn

The draw: Brooklyn has no shortage of trendy neighborhoods, since Manhattan drove out its creative class like medieval lepers. DUMBO and its neighbor, Brooklyn Heights, exemplify both the borough’s start-up cool and old line, brownstone chic. In the Heights, Truman Capote’s former home sold in 2012 for $12.5 million; a brownstone once used by Norman Mailer listed in April for $16 million. And DUMBO boasts the borough’s most glamorous (if perennially unsold) listing, the $18 million Clocktower Penthouse at 1 Main St. From cobblestone streets near the riverfront to unrivaled “forever views” from the bluff, these trendy neighborhoods offer Brooklyn’s own brand of artisanal real estate.

Who lives there: Tennis ace Andy Roddick and his model missus, Brooklyn Decker, occupy a DUMBO loft that typifies the neighborhood’s boho aspirations and Soho prices. Near-neighbor and Oscar-winner Anne Hathaway recently sold in the Clocktower building for $4 million. International Brooklyn poster girl Lena Dunham calls the Heights home—as does actor Paul Giamatti.

Neighborhood hangout: Trendy restaurants come and go, but the Brooklyn Bridge Park is here to stay. Locals flock to the riverside strip for its shady lawns, biking and jogging, and unrivaled view of the city.

Local indulgence: Paying list price for a book at one of DUMBO’s four independent bookstores. Berl’s Brooklyn Poetry Shop even has a Lego bust of Walt Whitman—who used to edit the neighborhood newspaper.

Long Island: North Hempstead, Oyster Bay and Huntington

The draw: Anyone who has ever read The Great Gatsby has sensed the allure of the mansions with lawns that slope down to yachts in this quintessential American playground. Picture an oil portrait of an old-time patriarch with muttonchops, clutching a scroll of plans in his dark study, and you have an image of the men who planted their money here: Vanderbilt, Guggenheim, Roosevelt, Whitney, Morgan and more. Today’s LIRR might not be as heroic as the railroad that generation built, but it crosses some valuable real estate. For many, the North Shore retains its dignity as a cut above the new money that has rattled toward the Hamptons. Oyster Bay is still the same pretty town that has inspired a century of writers and Broadway lyricists. McMansions can be had anywhere, but the Gold Coast has the foundation of history beneath its limestone terraces and wine cellars.

Who lives there: “Piano Man” Billy Joel is the North Shore’s most famous resident, whose waterfront estate on Centre Island provides a satisfying link to the area’s glamorous Jazz Age past. John McEnroe, Rupert Murdoch and broadcaster Sean Hannity are all current or former residents nearby.

Neighborhood hangout: Old money collects at the Seawanhaka Corinthian Yacht Club on Centre Island, which describes itself as “near enough to Manhattan to be convenient, but yet a world away.” If boating sounds too much like hard work, the club also offers tennis and croquet.

Local indulgence: A zippy little yacht is just the thing to park at the end of your dock on the Long Island Sound. Marquis makes a spiffy tri-deck model called the 720, with three staterooms, a large salon and a gourmet galley, for north of $3.5 million.

New York is its own fairytale kingdom, with stone towers along the park and country estates in every conceivable style. Does your taste run to modern French chateau, with a media room as big as the wine cellar? Or perhaps a waterfront “farm house” on 50 acres, with a price tag in the low nine figures? If you’re artistic, you might like a penthouse near the Chelsea galleries, or perhaps loft space in the heart of start-up Brooklyn, where the new bohemians look back on Manhattan and laugh. Whether you want to invest in location or lifestyle, the only question is, which modern Gold Coast is right for you?

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Additional reporting by Nicole Vranjican

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