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10 of The Most Incredible Real Estate Investments Ever

From Ellen DeGeneres’s show-stopping double flip to NYC’s storied Harkness Mansion sale, these properties may be worth their weight in gold—and then some.

Real estate is a fickle beast; But when she is kind, she is bounteous. The market has its cycles, and each time there’s a massive upswing in real estate values—the current expansion in values in most U.S. markets has been afoot for a record nine years—someone comes out a winner. Be that an early adapter in Brooklyn, the auspicious owner of a small island before a regional tech boom, or a buyer who timed their transactions just right. Those who come out on top in real estate investing inevitably pocket a hefty chunk of change.

Here, AD takes a look at some of the best property plays in recent history.

1/10 Locksley Hall, San Francisco

Photo: Neal Ward Properties

As San Francisco rent has risen higher than that in New York, by many measures, the city has also developed a luxury home market where prices tick in with the same blockbuster dollar amounts as in the Big Apple. For example, Locksley Hall, on Belvedere Island in Marin County, offers stunning views, a pool, and even a panic room, according to Curbed S.F. The estate, bought by mining mogul Robert Friedland in 1995 for a reported $5.5. million, sold for $49 million 20 years later. That price was actually $16 million shy of the asking price, although it still shattered the record for the area.

2/10 19 East 64th Street, New York City

Photo: Via Property Shark

Art collector David Wildenstein smashed the record for priciest Manhattan townhouse ever sold in April of this year, offloading 19 East 64th Street for over $79 million. But Wildenstein came close to an even sweeter deal: In 2014, the 25,000-square-foot four-story home with gilded marble interiors was nearly sold to the nation of Qatar, which hoped to house its consulate there, for $90 million.

3/10 The Mayflower Hotel, New York City

Photo: Via Creative Commons

When Herbert Sukenik moved into a room in the Mayflower Hotel on Manhattan’s Upper West Side around 1975, he likely had no idea that that decision would later net him millions of dollars. However, due to the strengths and quirks of New York City’s housing laws, that is what happened in 2005 when developers wanted to raze the hotel to build luxury condominiums. The book House of Outrageous Fortune, which chronicles the development of that condo building—15 Central Park West (pictured above), where Lloyd Blankfein would later become a resident—tells the tale of Sukenik, an eccentric bachelor whose neglected room in the storied hotel netted him a reported $17 million.

4/10 Fairholme Mansion, Newport, Rhode Island

Photo: Via Wikimedia

This 15-bedroom Gilded Age mansion, set among a croquet court and putting greens and abutting the Atlantic Ocean, was sold for $15 million in July of 2015, according to reports. Later that year, real estate developer Doug Manchester relisted the property asking $21 million, according to the Wall Street Journal. While the sale did not achieve that lofty sum, the property did nab a reported $16.1 million in February of 2016—not bad for seven months of ownership.

5/10 12 East 73rd Street, New York City

Photo: Via Property Shark

In February of this year, another townhouse on the Upper East Side of Manhattan traded in a pricey transaction: Island Capital Group Chairman Andrew Farkas sold his home at 12 East 73rd Street for $41 million—netting an $18 million profit over the ten years during which he held the asset.

6/10 Playboy Mansion, Los Angeles

Photo: Getty Images

Hugh Hefner bought his 29-room home in the Gothic-Tudor style, nestled high in Los Angeles’s Holmby Hills neighborhood, for $1 million in 1971, according to reports. Last year, he passed ownership to an investor, C. Dean Metropoulos for $100 million, with the condition Hefner retain an option to work and live in the home for the rest of his life.

7/10 Harkness Mansion, New York City

Photo: Via Property Shark

Swiss banking magnate Jacqui Safra bought this limestone mansion for $6.9 million in 1987. One of the widest townhomes available in Manhattan at 50 feet across, the house was unloaded at the height of the most recent real estate bubble. Private-equity kingpin J. Christopher Flowers dropped $53 million on the manse, before embarking on a massive renovation, in 2007. (He later sold it at a significant loss to notorious art dealer Larry Gagosian after his wife filed for divorce, parting with the stately home for $36.5 million in 2011.)

8/10 Madonna’s Beverly Hills Home

Photo: Westside Estate Agency

In 2013, the Material Girl sold her Beverly Hills digs to an unnamed “Wall Street big shot” for $19.5 million, according to TMZ. That big shot turned out to be a private equity investor, who in turn flipped the home at 9425 Sunset Boulevard, selling it for $27.9 million just a year and a half later.

9/10 1852 Deloz Avenue, Los Angeles

Photo: Tracy Do / Compass

As the internet will tell you, L.A. is cool now. And that coolness, when combined with Southern California’s only true native industry—real estate speculation—makes for some big ticket trades. This petite Spanish Colonial Revival home was sold in 2014 for $200,000 and flipped the next year for a whopping $915,000, according to Redfin.

10/10 Ellen Degeneres's Hollywood Hills Estate

Photo: Getty Images

DeGeneres bought a Hollywood Hills manse in 2005 for a “rumored $6.5 million,” as Forbes points out, before selling it in 2007 to Allison Millgard, a philanthropist. The host of the eponymous television show netted $3.5 million profit on that sale, the magazine says. But she was apparently not done with the house. Like a couple that remarries after a divorce, DeGeneres actually bought the house back in 2014, for $8.75 million, before again parting with it two years later—this time to Calvin Klein’s longtime business partner Barry Schwartz—for $1.1 million in profit, according to Variety, which dubs the actress “house-mad” for her many million dollar house flips.


Posted July 19, 2017

Article reposted from Architectural Digest. For link to full article, click here.

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