Flickr/WLCutler
Larry Ellison spent between $300 million and $500 million on a majority of Lanai.
No man is an island. Although, some men happen to own one.
We found the most expensive properties belonging to tech investors, entrepreneurs, and CEOs.
Some of the big tech personalities you’d expect to have extravagant homes actually live quite modestly. Yahoo CEO Marissa Mayer, for example, lives in a $5.3 million five-bedroom house in Palo Alto, California, and Tumblr CEO David Karp, who made over $1 billion on his company’s sale to Yahoo last year, lives in a $2 million duplex in the Williamsburg neighborhood of Brooklyn, New York.
Others, however, live in homes that scream “YOLO.” From Sean Parker’s 24-foot-wide West Village townhouse paneled with vintage subway car siding to Larry Ellison’s 98% share of the Hawaiian island of Lanai, any one of these real estate grabs will make you green with envy.
To estimate the approximate current market value of the houses, we looked at public assessors’ records and spoke to Kyle Egan, licensed real estate salesperson for Nest Seekers International, and Judy Citron, an agent with Alain Pinel Realtors.
30. Aneel Bhusri’s Bay-view villa
Estimated home value: $6.7 million
Title: Cofounder and CEO, Workday
The newly minted billionaire cofounder of human capital and financial software company Workday bought his two-story San Francisco home back in 2003 for about $5.5 million, making a solid $1.2 million as the home’s value appreciated.
With 11 rooms (four of which are bathrooms), a large basement, and nearly 4,600 square feet of space, Bhusri and his family enjoy pristine views of the San Francisco Bay and close proximity to nearby Baker Beach.
29. Mark Hurd’s Marymont Avenue Mansion
Estimated home value: $8 million
Title: Co-president, Oracle
Workday rival Oracle’s co-president one-ups Bhusri’s place in San Francisco with his own five-bed, six-and-a-half-bath beauty in Atherton, California.
The main house is just over 6,400 square feet, but the property boasts a pool house with its own kitchen and bathroom. A sweeping, roundabout driveway and perfectly manicured lawns complete the ensemble.
Hurd and his wife, Paula, purchased the home in 2005 for $7.1 million, according to city records, and today the home is worth about $8 million.
28. Jon Oringer’s Hudson River-view home
Estimated home value: $9 million
Title: Founder, Shutterstock
Thanks to the rising value of Shutterstock shares, Oringer became New York’s first techie billionaire and, naturally, he has a beautiful Manhattan apartment to match his status. His two-bedroom apartment in the West Village is in a building designed by Pritzker-winning architect Richard Meier surrounded by frameless glass. Many of the units in the buildings have balconies and direct Hudson River views.
Nest Seekers real estate broker Kyle Egan gives the apartment a conservative $9 million estimate.
27. Gideon Gartner’s luxurious penthouse
Estimated home value: $9.15 million
Title: Founder, Gartner Inc.
Gartner breaks even on his staggering penthouse apartment in the luxury Metropolitan Tower, according to broker Kyle Egan.
“With brand new projects hitting 57th Street like One 57 and 432 Park Avenue, values aren’t rising very much at Metropolitan Tower,” he says. “I believe that Mr. Gartner’s home is worth in the neighborhood of the $9.15 million that he paid for it.”
That being said, Gartner’s one-bedroom is still a stunning Manhattan sanctuary at nearly 3,000 square feet with limestone flooring and rosewood and silver finishes.
26. Jack Dorsey’s seaside manor
Estimated home value: $10.2 million
Title: Founder and CEO, Square; Cofounder, Twitter
Dorsey bought his cliffside mansion, which overlooks the Golden Gate Bridge and San Francisco Bay, in 2012 for just under $10 million.
The 3,700-square-foot house on El Camino Del Mar, built in 1965, features custom Brazilian wood cabinetry and a 20-foot retractable glass roof that functions as an enormous sky light.
According to records from the San Francisco Assessor’s office, the home is worth about $10.2 million today.
25. Larry Page’s comfortable cul-de-sac
Estimated home value: $12 million
Title: Cofounder and CEO, Google
The Google cofounder owns two lots off Palo Alto private court Waverly Oaks that, combined, give him more than 47,000 square feet of land.
One of the lots has a massive six-bed, six-bath home sitting on it; the home alone is 8,000 square feet. Page bought the place in 2005 for about $7 million, but today public assessor records indicate it’s worth closer to $8 million. On the other lot, Page built a near-6,000-square-foot green home out of organic materials and low-volatility paint, worth about $4 million today.
But rumor has it that Page also bought up a bunch of other properties in the same cul-de-sac, which would make the $12 million value a pretty conservative estimate.
24. Sheryl Sandberg and David Goldberg’s upgraded smart house
Estimated home value: $12.5 million
Title: COO, Facebook; and CEO, SurveyMonkey
In February 2012 The Wall Street Journal reported that Sandberg and her family were building a modern-looking house in Menlo Park, near Facebook’s offices, of nearly 9,200 square feet.
The Sandberg-Goldberg family bought the property in 2009 for just shy of $3 million and have now transformed it into their eco-home of the future with a green roof and solar panels. The large basement houses a wine cellar, gym, movie theater, home office, and guest room. The property also has a waterfall and basketball court but, sadly, no pool.
Judy Citron, an agent with Alain Pinel Realtors, says Menlo Park property values have skyrocketed 21% in the second quarter year-over-year, while inventory has dropped off. She estimates the current market value at $12.5 million.
23. Tom Proulx’s mansion triad
Estimated home value: $13.5 million
Title: Cofounder, Intuit; Chairman, Netpulse
Proulx’s three adjacent homes are valued each at $4.6 million, $6.1 million, and $2.8 million, according to the San Mateo Assessor’s office, bringing the combined value of the properties to about $13.5 million.
The three stunning homes sit on 11 Atherton acres that, according to a 1997 Businessweek article, have a 9-hole golf course out back. The houses themselves are protected by a “Jetsons-style ‘smart house’” security system.
22. Sergey Brin’s Big Apple apartment
Estimated home value: $15 million
Title: Cofounder, Google
Brin’s duplex penthouse apartment in Manhattan’s Greenwich Village takes up the top two floors of his building and is an expansive near-3,500 square feet. He bought the place in 2008 for $8.5 million, making good use of four bedrooms, heated limestone floors in the bath, and a 23-foot wraparound balcony with multiple outdoor living areas.
Nest Seekers real estate salesperson Kyle Egan puts the value of the place at about $15 million, noting that “the scarcity of penthouse condos in the West Village coupled with a strong demand will continue to drive the value of this property.”
21. Mark and Alison Pincus’ Dutch Colonial
Estimated home value: $15.6 million
Title: Cofounder and CEO, Zynga; and Cofounder, One King’s Lane
The Pincuses bought a beautiful Dutch Colonial-style San Francisco home for $16 million in 2012, right in the same neighborhood as a number of other prominent startup founders. There are seven bedrooms, six full bathrooms, and four half-bathrooms throughout the four-story, 11,500-square-foot house.
There’s also an elevator, in case the stairs seem like too much work. Other amenities include eight fireplaces and large picture windows with bay views. Public records put the home at about $15.6 million today.
20. Gary Bloom’s Isabella Avenue digs
Estimated home value: $16.99 million
Title: CEO, MarkLogic
If the CEO of MarkLogic ever wants to talk tech with his neighbors, he can always take a stroll down the street to see former Yahoo CEO Carol Bartz, who lives on the same Isabella Avenue block.
Bloom’s home, which was built in 2004, is 8,500 square feet with four bedrooms, four bathrooms, and one half-bath, with a clean, manicured lawn. The San Mateo County Assessor’s Office indicates the property is worth just under $17 million today.
19. Elon Musk’s Bel Air bounty
Estimated home value: $17 million
Title: Founder, Tesla and SpaceX; Chairman, SolarCity
In January of last year Musk bought a $17 million Bel Air mansion with seven bedrooms and nine bathrooms. The 20,000-square-foot home drinks in romantic views of both the city and the Pacific… and now also his new, smaller mansion across the street, which he bought for $6.75 million back in October.
The larger mansion, at any rate, comes with only the most luxurious accoutrements, like a two-story library, a theater, guest suite, tennis court, wine cellar, gym, pool, and five-car garage.
18. Mark Cuban’s Dallas palace
Estimated home value: $17.3 million
Title: Cofounder, Broadcast.com; Owner, Dallas Mavericks
Cuban’s Dallas sprawl is the ninth-most expensive home in the city, built in 1997. The outspoken investor and “shark” on ABC’s “Shark Tank” shows that it is still possible to do business in tech from somewhere other than New York or Silicon Valley. Living in Dallas also gives Cuban, the owner of the Dallas Mavericks, plenty of opportunity to attend games.
According to Dallas public assessor records, his home is worth an estimated $17.3 million — not too shabby for 24,000 square feet, 10 bedrooms, and 13 bathrooms.
17. The Winklevii’s modern mansion
Estimated home value: $18 million
Title: Cofounders, ConnectU
The Winklevoss twins, who famously sued Facebook’s Mark Zuckerberg for allegedly taking their idea for a college-based social network, purchased a contemporary 8,000-square-foot power pad in the Hollywood Hills for $18 million in 2012. Public assessor records indicate the value of the home remains the same today.
The house has an outdoor pool and beautiful panoramic views of downtown Los Angeles. Tyler Winklevoss spends most of his time at their Hollywood Hills home, while Cameron runs the East Coast branch of Winklevoss Capital at their New York City HQ — possibly while living in a brand-spanking-new, $14.5 million Soho penthouse, if rumors are true.
16. Fred Wilson’s prime Village real estate
Estimated home value: $20 million
Title: Cofounder, Union Square Ventures
The prominent venture capitalist, who is known for his smart investments in high-profile tech companies like Twitter, Tumblr, and Foursquare, lives in a gorgeous West Village penthouse that he bought in 2010 for $13 million.
Licensed real estate salesperson Kyle Egan estimates Wilson’s pad to be worth at least $20 million, if his unit is about the same size — about 6,200 square feet — as other full-floor units in the building. Wilson’s apartment, according to Egan, has “double-height living spaces, large warehouse-style windows, and multiple terraces, making it a very desirable product for the neighborhood.”
15. Eric Schmidt’s Spanish-style casa
Estimated home value: $21.4 million
Title: Executive Chairman, Google
The former Google CEO purchased his more than 7,000-square-foot home in Montecito, California, from comedian Ellen DeGeneres and actress Portia de Rossi for a reported $20 million in 2007. The value crept up from $21.3 million year-over-year, according to Santa Barbara’s public assessor’s office.
The heavily secured compound boasts a four-bedroom main house designed by renowned California architect George Washington Smith, a championship grade tennis court, and a colorful tiled fountain. Still, he’s had trouble renting out the home for weddings since 2012, when Kim Kardashian married New Jersey Net Kris Humphries there and spoiled the property with their bad juju.
14. Peter Thiel’s South Maui sanctuary
Estimated home value: $25.5 million
Title: Cofounder, PayPal; investor and entrepreneur
Thiel made the biggest single-family real estate purchase in the history of Maui with his $27 million home on the island of Maui back in 2011. Today the Maui County public assessor’s office evaluates the property and home at about $25.5 million.
Situated on the Makena waterfront, the beach home is made up of four interconnected pavilions wrapped around a courtyard and swimming pool.
The early Facebook investor also owns homes in the Marina District in San Francisco, Los Angeles, and New York City, according to Variety.
13. Jeff Bezos’ palatial Beverly Hills palace
Estimated home value: $26.8 million
Title: Founder and CEO, Amazon
The CEO of the Everything Store really does have it all, including a private estate in Medina, Washington, three linked apartments in Manhattan’s Century Tower, and this Beverly Hills sprawl. The listing for his most expensive home, reportedly down the street from Tom Cruise’s residence, says it has soaring beam ceilings, a master bedroom with a private veranda, a six-car garage, and private suites for the maids.
According to the Los Angeles County public assessor’s office, the property plus improvements totals $26.8 million.
12. Ted Waitt’s glassy Bel Air enclave
Estimated home value: $29 million
Title: Cofounder, Gateway Computer
From one tech family to another — Larry Ellison’s film producer daughter Megan spun off one of three mansions in the notable Bird Streets neighborhood to Waitts last year, for a cool $20.5 million. Improvements to the home increased its value by nearly $9 million, according to the Los Angeles public assessor’s office.
The house is apparently a gated “micro-compound” with four bedrooms, seven bathrooms, and unobstructed city views, with a curved wet bar in the living room and a state-of-the-art fitness center on the second floor.
11. David Sacks’ place on “Billionaire Row”
Estimated home value: $29.5 million
Title: Founder, Yammer (acquired by Microsoft)
Fresh off his startup’s $1.2 billion exit, tech mogul Sacks paid $20 million for an unfinished estate on Broadway Street — making it one of the biggest home sales in San Francisco real estate history. Local brokers estimated the cost of renovations would be upward of $10 million; but it’s paid off. Current market value skyrocketed $9.5 million year-over-year, according to the San Francisco County public assessor’s office.
The 17,500-square-foot property has 10 rooms, four bathrooms, a separate 6,000-square-foot guest house, and mega clout.
10. Sean Parker’s West Village cathedral
Estimated home value: $30 million
Title: Cofounder, Plaxo, Napster, and Airtime; Founding President, Facebook
Parker, best known as the cofounder of Napster and an early investor in Facebook, is also the proud owner of a 24-foot-wide townhouse in one of the New York’s hottest neighborhoods, Egan says. The Bacchus House, named after the Roman god of wine, is a work of art with natural ivy on the exterior, a magnificently landscaped atrium, and astounding decor like graffiti art walls and an entryway paneled with vintage subway car siding.
It also offers rare amenities like a private garage and an indoor pool.
“His $20 million purchase in 2010 was a smart investment being that townhouses nearby are currently asking $400-$500 per square foot,” Egan says. “I estimate the value of Mr. Parker’s property at $30 million today.”
9. Trevor Traina’s 1905 Georgian-style home
Estimated home value: $30.2 million
Title: Founder, CompareNet, DriverSide, IfOnly
Serial entrepreneur Trevor Traina and his wife, Alexis, bought a $35 million home on San Francisco’s “Billionaire Row” last year, making it the most expensive home ever sold in the city. Its features match the price tag — sweeping views of the Golden Gate Bridge, a conservatory filled with plant life, velvet-lined walls, and a heated outdoor spa.
Below the house is a 3,000-square-foot basement blown out of solid granite, built to display his 300-piece photography collection out of sunlight.
8. Mark Zuckerberg’s Palo Alto block
Estimated home value: $44.7 million
Title: Founder and CEO, Facebook
When The Zuck heard that the developers of a property neighboring his Palo Alto five-bedroom home were going to build a mansion on it and market it as “next door to Mark Zuckerberg,” he had to act fast. The Facebook founder paid more than $30 million in total, according to the San Jose Mercury News, for the four residences next to his. Three other nearby homes were snatched up a month later by Iconiq Capital — a San Francisco firm that handles financial matters for Zuckerberg — and its affiliates, bringing his real estate portfolio to approximately $44.7 million.
“He has no plans to build a Taj Mahal on the land, according to a person with knowledge of the transactions,” the Mercury News writes. “Zuckerberg is leasing the existing homes back to the families that live there.”
His personal party pad has heated floors, a natural pond with waterfall, and a tech-savvy kitchen, according to the agent.
7. Omid Kordestani’s 15 CPW sprawl
Estimated home value: $45 million
Title: Senior Advisor to the Office of the CEO and Founders at Google
Kordestani is known for being one of the original Googlers — the 12th employee, to be exact — and that kind of clout buys you a unit in the holy grail of Manhattan apartments. His four-bed, six-and-a-half bath apartment neighbors Sting and Goldman Sachs CEO Lloyd Blankfein, and it boasts a 405-square-foot terrace.
“Fifteen Central Park West houses units that command some of the city’s highest prices, and Mr. Kordestani’s 5,400-square-foot apartment is no exception,” Egan says. “The current offerings are asking as much as $9,000-$10,000 per square foot. Being that the apartment benefits from private outdoor space and Central Park views, I believe the apartment is worth $45-$50 million today.”
6. Yuri Milner’s massive French chateau
Estimated home value: $46.2 million
Title: Investor in Facebook, Zynga, Twitter, Spotify, ZocDoc, 360Buy.com, and Groupon
For whatever reason, Milner overpaid for his Silicon Valley mansion by 100%, a Santa Clara County assessor told Forbes. The home was worth $50.27 million — four million more than its value today, according to public records — while the tech billionaire shelled out a jaw-dropping $100 million in 2011.
He certainly got his money’s worth. The 25,000-square-foot French chateau, known as Palo Alto Loire Chateau, perches on 11 acres of prime Los Altos Hills real estate with views of the San Francisco Bay. In addition to five bedrooms and nine bathrooms, the home comes equipped with a ballroom, private theater, wine cellar, and indoor swimming pool.
5. Richard Branson’s private island
Estimated home value: $60 million
Title: Founder of Virgin Group and investor
A 27-year-old Richard Branson coughed up £60,000 for Necker Island, a 74-acre patch of land in the British Virgin Islands, more than 30 years ago. Six years later, he opened the doors to a luxury retreat that accommodates just 30 guests.
Over the years, Necker Island has served as a hidden getaway for Mariah Carey, Oprah, Rod Stewart, Kate Moss, Princess Diana, and Kate Winslet. But privacy doesn’t come cheap. Guests are forced to rent the entire island for a cool £39,000 per night.
After the Great House tragically burned to the ground during Hurricane Irene, Branson spent £9 million rebuilding it from the ground up. He estimated in 2006 that the island’s value had grown to approximately $60 million, a 33,233% increase over what he paid for it.
4. Michael Dell’s “Raptor Residence”
Estimated home value: $64.8 million
Title: Founder and CEO, Dell
The Big Island of Hawaii’s Kona coast is a magnet to billionaires in the market for vacay homes. The Dell founder owns a sprawling oceanfront property in the gated community of Kukio.
According to the County of Hawaii public assessor’s office, the Raptor Residence could fetch nearly $65 million. Luxury real estate blog The Pinnacle List says it’s the most valuable property in the Sandwich Islands.
The 23-room, single-level home channels both modern contemporary design and distinctly Hawaiian architecture, blending separate pavilion structures with outdoor spaces.
3. Paul Allen’s nine-home estate
Estimated home value: $116.2 million
Title: Cofounder, Microsoft; Chairman, Vulcan
Seattle native Allen owns homes in Manhattan, Atherton, Malibu, Beverly Hills, Hawaii, London, and St. Jean Cap-Ferrat, France, but none are as impressive as his estate on Mercer Island, Washington, close to where he grew up. Nine structures spread across 11 parcels of land add up to a value of $116.2 million, according to the King County public assessor’s office.
While Allen mainly occupies one of them, one is occupied by his mother, and many others serve as guest homes to friends and celebrities alike (he has never been married and has no children). The homes come with some pretty fantastic features, including a floating helipad, an NBA-regulation-size basketball court, an enormous fitness center, a ballroom, a gorgeous swimming pool with a water slide, and thousands of square feet of water frontage.
2. Bill Gates’ futuristic Medina, Washington, home
Estimated home value: $120.6 million
Title: Cofounder and Chairman, Microsoft
The Microsoft titan’s mansion is so epic, it has its own Wikipedia page, as Curbed Seattle notes.
Xanadu 2.0, as it is known, covers 66,000 square feet, took seven years to build, and is worth $120.6 million, according to the King County public assessor’s office.
Naturally, the home is decked out in tech. The swimming pool uses an underwater music system; speakers are hidden beneath the wallpaper so tunes can follow you room to room; and guests can alter any room’s temperature, music, and lighting by transmitting their preferences through a wearable device.
1. Larry Ellison’s private Hawaiian island
Estimated home value: $300 million to $600 million
Title: Cofounder and CEO, Oracle
An overwhelming majority of picturesque Lanai rests in the clutches of Oracle titan Ellison. In a groundbreaking 2012 deal, he scooped up 98% of the Hawaiian island for an undisclosed sum, rumored to be between $300 million and $500 million.
It has been a neverending shopping spree since. Ellison owns every hotel room, the inter-island airline Island Air, and roughly nine homes near the Four Seasons Resorts Lanai at Manele Bay for more than $41 million, ABC News reports.
Ellison aims to develop Lanai as a model for environmentally sound living. He has other plans in mind for the rest of his real estate portfolio — including homes in Lake Tahoe, Nevada; Newport, Rhode Island; Malibu, Rancho Mirage, San Francisco, and Woodside, California; and Kyoto, Japan.
“My favorite museums are things like the Frick Museum in New York and the Huntington Hartford in Pasadena where it’s someone’s home that you walk through,” Ellison said to CNBC. “So I’m going to start these art museums that are basically converted homes.”
Now see where Wall Streeters put down roots.
The Most Expensive Homes In Finance, Ranked! »
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