Fantasy and Realty
ALL OF US have to live somewhere, and what we call home says a lot about who we are as individuals, and as a nation. According to the US Census Bureau, of the more than 115 million homes in the US, 8% are mobile homes, 17% are apartments, 10% are in 2-4 unit buildings, and 60% are single-family detached structures, what is generally understood to be a “house.” The value of the average American home, incidentally, is around $200,000.
At the top end of the real estate market, the idea of home takes on spectacular dimensions, and spans the nation. With internet tools like Trulia and Zillow, homes currently on the market for $10 million or more can be found in abundance. Mapping the places where the highest concentration of these homes appear, from the Hamptons to Malibu, presents a national realm of fantasy realty, where the American Dream is as vivid and obtainable as the horizon.
Coastal New England
The coast of New England provides the historic context of colonial settlements and early industrialists’ ocean-front manors that evoke the estates of England, transposed and transformed in the New World. This is where the traditional old money of America roosts, among the convoluted coast from Maine to Connecticut, and among the islands of Massachusetts. 
The most expensive homes on the market in New England are often found on Nantucket, an island off Cape Cod. Nantucket has a year-round population of 10,000, which grows to 50,000 in the summer. Tommy Hilfiger, whose fashion line evokes the affluent beach life of the island, built one of the most expensive homes on Nantucket. Entertainment celebrities, CEOs, and politicians, like John Kerry, have homes here too.
A close second for the most expensive real estate market in New England is the adjacent island of Martha’s Vineyard. The Vineyard is a political and celebrity playground, frequented by the Kennedys, Clintons, and Obamas, and where politically connected celebrities like James Taylor have summered for decades. It is larger and more touristed than Nantucket, and usually has fewer homes exceeding $10 million on the market, though properties exceeding $100 million have sold on the Vineyard in the past.
Newport, a town on a peninsula in coastal Rhode Island, is famous for its Gilded Age seasonal mansions (called cottages at the time), built by the barons of New York and Boston, like the Vanderbilts and Astors, and where the architects that built the mansions, including Charles McKim, Stanford White, and H. H. Richardson, also had homes. Though some of the mansions of Newport have been turned into museums and schools, many remain in private hands, and are among the most conspicuous displays of large living in the nation. The scale and pedigree of these homes continues to support a robust real estate market, where one of the most expensive homes for sale is actually not a Gilded Age palace, but a house built in 2009, with an asking price of $45 million, and a relatively modest 7,698 square feet of space. Perhaps that is why it has been listed for more than two years, despite its 45-acre seafront lot.
Greenwich is the closest Connecticut community to New York City, less than 40 minutes by train to Grand Central Station. Like the London borough after which it is named, the houses here tend towards the English estate style, with large lawns, classical statuary, and privacy. With its proximity to New York, and its jutting peninsulas and leafy hills, Greenwich has become one of the most affluent towns in the country. Residents have included celebrities like Ron Howard, Mary Tyler Moore, Glenn Close, Regis Philbin, and Mel Gibson, whose house on Old Mill Road was on the market a few years ago for $39.5 million. Investment bankers, including several of the top 50 richest people in the country, have homes here, such as Ray Dalio, Thomas Peterffy, and Steve Cohen. Last year a shorefront property, Copper Beech Farm, sold for $120 million.
Just over the town line is Westchester County in New York, where the Clintons have a comparatively modest but very secure house in Chappaqua, and where dozens more billionaires have large spreads with formal gardens, including George Soros and Michael Bloomberg, who seems to have homes in all the hot spots.
New York: The Top Tier of High Living
The two big islands of New York, Manhattan and Long Island, work together to serve the needs of the cultural and financial elite of America. Manhattan, the nation’s densest cluster of commerce and culture, is a complex machine for generating revenue, while the Hamptons of Long Island, a selectively social getaway for Manhattanites to spread out and let off steam, provides space to spend even more money on real estate.
The island of Manhattan is the most valuable cluster of residential real estate in the nation, and likely the world. Usually half of the top 25 highest priced home listings in the nation are in Manhattan, and most of them are at the top of buildings, such as the three-floor penthouse at the Pierre Hotel, recently on the market for $125 million.
Townhouses often top the list, such as the Upper East Side mansion that sold recently for $114 million, or the block of several adjacent townhouses bought independently, and secretly, by Russian oligarch Roman Abramovich for more than $70 million, in order to integrate them into one of the city’s largest mansions.
To list the celebrities, business owners, politicians, and Forbes listers that have homes in Manhattan would be meaningless (though celebrities buying or selling $50 million apartments here recently include David Geffen and Steve Wynn). Since property ownership is a matter of public record, the efforts to own some of the most expensive real estate in the world anonymously leads to some fairly convoluted corporate shell games.
For some, relief from the intense urbanity of Manhattan is provided by heading a hundred miles east to the Hamptons, on the southern shore of the far end of Long Island, where typically more than a hundred homes are on the market for more than $10 million.
The Hamptons are the towns of East Hampton and Southampton, which have a couple dozen villages and hamlets within them, such as Sag Harbor, Montauk, Amagansett, Bridgehampton, and Sagaponack, which is often cited as the most expensive zip code in the USA, with a median home sale price of more than $5 million.
South of the arterial Highway 27, homes are closer to the ocean and tidal bays, and generally command the most money. Southampton’s Mecox Bay, for example, where Alan Alda and Richard Gere have homes, recently featured a house on the market for $85 million. A tidal bay in East Hampton known as Georgica Pond, where Steven Spielberg, Martha Stewart, and Kelly Klein have homes, had a house listed last year for $140 million.
Between the two, facing the ocean, is one of the largest and most extravagant private homes in the nation. Known as Fair Field, it is a 25 bedroom, 62,000 square foot Neoclassical palace with multiple outbuildings, including a 10,000 square foot private museum for the owner’s art collection, on 63 acres of ornate gardens, built in the 1990s by the industrialist investor Ira Rennert. Its value today is estimated at around $500 million (not including the art, of course).
Florida: Four Seasons of Sand and Sea
The beaches of Florida have been a favored getaway from the nation’s urban centers, most of which are below freezing in the winter. A strip along the southeast edge of the state, facing the Bahamas, has become most popular among those with the means to live largest–especially the region around Palm Beach and Miami Beach, where homes commanding the highest prices can be found.
Standard Oil millionaire Henry Morrison Flagler is often cited as the master developer and promoter of Florida real estate, and Palm Beach is the nidus of his empire. It was here that he established two luxury resort hotels, and sold lots to his social circle, which included the barons of the Gilded Age. It is also where he died in 1913 after falling down the stairs in Whitehall, his 55-room Palm Beach mansion, which is now the Flagler Museum.
Some of the most expensive real estate listings in the country have been located here over the years, such as the Ziff family’s compound, a few miles south of Palm Beach, listed in 2015 for $200 million. People who have owned homes in the Palm Beach area include many people with homes in the Hamptons, too, like Michael Bloomberg and David Koch (currently the eighth and fourth richest Americans, respectively) as well as famous performers of the past and present, like Jimmy Buffett, John Lennon, Michael Jackson, and Celine Dion, who built her fantasy home at Jupiter Island, north of Palm Beach, and put it on the market last year at $62 million.
Radio celebrities Rush Limbaugh and Howard Stern have had homes in Palm Beach, as have many CEOs and investment bankers, like Donald Trump, Ronald Perelman, and John Sculley, as well as politicians, including the former Prime Minister of Canada, Brian Mulroney.
Like Palm Beach, a barrier island separated from the shore by the intracoastal waterway, Miami Beach is a strip of sand too, across from the city of Miami. Historically associated with mobsters like Al Capone and Meyer Lansky, Miami Beach was developed largely by automotive industrialists, like Harvey Firestone and Carl Graham Fisher, the legendary national road builder who helped develop the interstate system. His Dixie Highway connected Detroit to Miami Beach, its southern terminus. He made Fisher Island, at the southern tip of Miami Beach, from scratch by dredging sand from the ocean bottom. Once an exclusive Vanderbilt family estate, home owners on Fisher Island today include celebrities Oprah Winfrey, Julia Roberts, and Mel Brooks. Carl Graham Fisher later went on to develop highways and real estate in the Hamptons.
This stretch of coast, from the chic and cosmopolitan city of Miami on Biscayne Bay, to Fort Lauderdale 25 miles north, is the other most expensive strip of land in Florida. Homes are often listed for more than $100 million, such as the $139 million Palais Royale in Fort Lauderdale, which has an Imax movie theater and a $2 million staircase, and Leona Helmsley’s old place in Coral Gables, on the market last year for $67 million.
Head for the Mountains
The Rocky Mountains provide space for expansive Alpine lodges with grand views of snowcapped peaks and pine forests, and recreational fun, especially skiing in the winter (and fishing, horseback riding, and golf in the summer). The most expensive residential mountain retreat communities in the nation are Aspen, Colorado; Vail, Colorado; Jackson Hole, Wyoming; Sun Valley, Idaho; Park City, Utah; and Lake Tahoe, Nevada/California. 
The Sun Valley region of Idaho includes the towns of Ketchum and Hailey. Ernest Hemingway may have made this region famous, but its ski resorts and scenic mountains sustain its popularity, and its annual media and tech mogul conference at the Lodge in Ketchum helps keep up its reputation for exclusivity. There are typically more than ten homes on the market with asking prices higher than $10 million, but rarely for much more than $20 million.
Jackson Hole is a valley at the base of the Grand Teton Mountains of Wyoming, and includes the towns of Jackson and Wilson. Near Yellowstone and Grand Teton National Parks, there are a few ski resorts nearby. The area usually has around a dozen homes listed for more than $10 million, and ranch land listed for up to $40 million. Christy Walton, a Walmart heiress and the ninth richest American (according to Forbes), has a house in the Valley, as well as Forrest Mars Jr., #16 on that richest American list. Bill Gates, #1 on the list, has a big spread near Cody, Wyoming, about 80 miles from Jackson Hole.
Vail’s ski resort opened in the 1960s, and by the 1980s it was the largest ski area in the nation. Located less than two hours from Denver, Interstate 70 runs along the base of the mountain, and resorts and homes are wedged in between the slopes and the Interstate. Despite this, there are usually more than a dozen homes on the market here for more than $10 million, especially those at the base of the ski runs, where you can ski directly to your door.
The mountain region with the highest value real estate listings in the nation is the adjacent ski resort communities of Aspen/Snowmass in Colorado. In Aspen, you can ski into the downtown grid of the former mining town, now replete with expensive shops and restaurants, and a new contemporary art museum. Also in town is the Aspen Institute, a famous political and cultural think tank, host to the annual Ideas Festival, which brings cultural, business, and political celebrities to town, and helps to give the community its upscale European élan.
Though a few billionaires have homes in town, including Charles Koch (Forbes-listed with his brother as the fourth richest American, and a major supporter of the Aspen Institute), it’s the hills and dales outside of town where the real estate soars. Charles’ other brother, William Koch, listed his 15-bedroom mountain home for sale last year for $89.9 million, for example. Around 50 American billionaires are said to have homes in the region.
Park City, a former mining town an hour’s drive from Salt Lake City, is now a base for two ski resorts. Though the snow is better at the more distant Alta and Snowbird, the Park City environs have more services and retail, and a quaint downtown. It is the location for the annual Sundance film festival, which helps to give the community some international flair. There are usually at least a dozen houses on the market there for $10 million or more.
Lake Tahoe’s clear water and proximity to ski areas make it a favorite mountain retreat for the affluent, especially from around the San Francisco Bay Area, less than four hours away by car. Lake Tahoe is in the Sierra Mountains and is split by the state line between California and Nevada. The most expensive homes tend to be on the Nevada shores, in communities like Incline Village and Crystal Bay, where Howard Hughes and Larry Ellison owned homes that have since sold for more than $20 million, and Glenbrook, which had a listing last year at $98 million. Houses at the high end of the market can sit for a long time until finding a buyer, especially during a recession. An especially dramatic home called Tranquility, in the Nevada community of Zephyr Cove, was listed for $100 million by its owner (a co-founder of the Tommy Hilfiger company) in 2006. It finally sold in 2013 for $48 million.
Northern California's Temperate Mediterranean Splendor
Northern California’s landscape is one of the most varied in the nation, and includes Alpine plateaus, volcanoes, rugged remote coasts, and lush river valleys. With the San Francisco Bay area as its cultural and economic anchor, many have made their fortunes here, and established their personal paradise within the Mediterranean hills and dales of the region.
Napa Valley, northeast of San Francisco, is a contoured and constructed landscape of vineyards and villas, evoking the French and Italian analog that in many ways it has surpassed. Several estates are usually on the market listed for more than $20 million, especially around the town of St. Helena. Dramatic architectural extravagances can be found tucked down private roads, often part of productive wineries. Hollywood celebrities have clustered here, most famously the director Francis Ford Coppola and actor Robin Williams, a dedicated Bay Area booster, who commissioned a winery estate for himself here in 2003, which, after his death in 2014, went on the market for $25.9 million.
Tiburon is a peninsula jutting into San Francisco Bay across from Sausalito that is often cited as one of the most affluent zip codes in the nation. Its steep hills enable homes to see over one another, providing many opportunities for dramatic views across the bay and the scenic skyline of San Francisco. Tiburon is a favored community for executives from Bay Area’s prominent post-World War Two boom businesses, like Chevron and Bechtel. There are usually several listings above $10 million on the small and dense peninsula (which includes the town of Belvedere) and listings as high as $50 million have appeared over the last year.
Woodside is a town that spans the hills behind Silicon Valley, nearly to the Pacific Coast, south of Half Moon Bay. Its relatively open hillsides provide space for large estates for magnates from the railroad days to the present tech boom. In one example, Steve Jobs bought an estate originally built by the copper mining pioneer Daniel Jackling. Investor Charles Schwab has a home here, as does Oracle’s Larry Ellison. Singer Neil Young has lived here for decades. Homes often list for over $40 million. Atherton, an adjacent town mostly in the valley, is currently the third most affluent zip code in the country, and usually has a dozen house listings over $10 million. Google founder Sergey Brin has a comparatively modest house in the Palo Alto Hills, while Larry Page, his Google partner, lives in the leafy grid of Old Palo Alto, a block away from Steve and Laurene Jobs’ primary residence.
Once famous as an artist colony, occupied by photographers Ansel Adams and Edward Weston, and writers Robinson Jeffers, Robert Louis Stevenson, Jack London, and Sinclair Lewis, Carmel, on the Monterey Peninsula north of Big Sur, is among the fanciest towns in the nation. Carmel usually has several listings over $10 million, and a few over $20 million near the famous golf courses at Pebble Beach, one of seven golf courses on the peninsula. The town of Carmel-by-the-Sea, where longtime resident and actor Clint Eastwood served as mayor for a time, is a grid of hundreds of small residential lots each with an average value around $2 million.
Southern California: Sunset in Paradise
With its views of the setting sun into the Pacific Ocean, and ocean air keeping the temperature within reason, the coast of Southern California is, for many, paradise. Nearly everyone who can afford to live anywhere has a home here.
Southern California’s coastal affluence begins at Santa Barbara, whose hinterlands include Michael Jackson’s Neverland and Ronald Reagan’s Rancho del Cielo. The Spanish Colonial Revival town of Santa Barbara and its unincorporated communities along its coast, like Montecito, typically have dozens of properties listed for over $10 million, with some over $100 million. The list of famous residents, past and present, is long, and includes Oprah Winfrey, Jennifer Aniston, Jeff Bridges, Julia Child, Warren Christopher, Tom Cruise, Robert Duvall, Jane Fonda, Martha Graham, Jennifer Lopez, Dennis Miller, Steven Spielberg, and Warren Zevon.
Malibu is a narrow strip of a town along 21 miles of coast between Oxnard and Santa Monica, with an official population of 12,500 people. Whether officially declared as residents or not, the number of celebrities and Forbes 500 listers who have oceanfront homes here is rivaled only by the Hamptons. Oracle’s Larry Ellison owns at least nine homes along Carbon Beach in Malibu, in a section known as Billionaire’s Beach. David Geffen’s house, famous for blocking beach access, and for being lampooned in Doonesbury comic strips, was put on the market in June of 2015 for $100 million.
The hills along the northwestern edge of Los Angeles, from Pacific Palisades to Hollywood, an area around 12 miles long and 3 miles wide (roughly the size and shape of Manhattan), contains more large, expensive, and infamous domiciles than anywhere in the world. From Brentwood, west of the 405 Freeway, eastward to the 101 Freeway at Universal City, the windy roads sprawl into the hills through a battery of north-south canyons, through the communities of Bel-Air, Beverly Crest, Beverly Hills, and the Hollywood Hills. Along the base is Sunset Boulevard, and on top, Mulholland Drive. Though house prices have surpassed $200 million before, one developer, Nile Niami, is currently building a 100,000 square foot hilltop house in Bel Air that is expected to be listed at $500 million, more than twice what any house has ever sold for in the USA.
Affluence continues down the coast of California south of Los Angeles, where the most consistent and pleasant weather in the nation can be found. The Orange County community of Newport, with its manufactured peninsulas and islands, where you can park your yacht outside your house, usually has a dozen houses on the market for more than $10 million, and even more can be found further south at Laguna Beach, where a few homes are usually on the market for $20 million or more. The nation’s second wealthiest person, Warren Buffett, once had a second home in Laguna Beach. He sold it in 2006, and now the only residence he owns is in Omaha, Nebraska, which he bought in 1958 for $31,500.
The adjacent San Diego County communities of Del Mar, Rancho Santa Fe, and La Jolla, north of the city of San Diego, make up the most expensive part of the county, where listings for more than $10 and $20 million are frequently found. Rancho Santa Fe is inland a few miles, but still commands high values for large compounds with coastal views, or not. It became famous for the Heaven’s Gate cult’s mass suicide in a mansion there in 1997. Del Mar is the coastal area next to Rancho Santa Fe, separated from La Jolla by the Torrey Pines Golf Course. The hilly shores of La Jolla are more “old money” California, where Theodor Geisel (Dr. Seuss) lived, and where Raymond Chandler retired, once he was done with Los Angeles.
What about Hawaii?
2,500 miles beyond the sunsets of California’s coast is the ultimate Pacific paradise–Hawaii. Many of the people who could live anywhere have a home here, though they may be too busy to be there much.
On the big island (Hawaii), the adjacent communities of Kamuela and Kailua Kona, where Michael Dell and Paul Allen have homes, are the most expensive, with a dozen homes currently on the market for $10 million or more. Homes near Honolulu and Kailua, on Oahu, and on Kauai, can be similarly priced. The same is true in the community of Lahaina, on the island of Maui, where many Hollywood celebrities have homes, including Oprah Winfrey.
Tech giant Oracle’s founder and CEO, Larry Ellison, perhaps the largest collector of high-end real estate in the nation, recently bought 141 square miles of the island of Lanai, a former pineapple plantation island off the west shore of Maui–98% of the entire island–for an estimated $600 million. The part of the island he wasn’t able to buy is the town in the middle of the island, where Lanai’s 3,000 residents live. ♦
