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The 25 Most Expensive Homes in Hawaii

Michael Keany

Photo: Ryan Siphers

If you want to own one of Hawaii’s top homes, it helps to be in computers or investment banking. Using public records collected by Title Guaranty Hawaii, we’ve compiled a list of Hawaii’s priciest homes—exclusive compounds filled with sprawling swimming pools, personal tennis courts and stunning oceanfront views, places for which the annual property-tax bill runs a cool half-million.

The Top-25 Club turns out to be a who’s who of tech CEOs, venture capitalists and other financial-service barons, almost all from out of state. These are people not only rich enough to afford one $20 million house, but several of them, in different parts of the world.

The distribution of these palatial properties is also illuminating. Oahu has some famously expensive neighborhoods, such as Kahala, Portlock and Lanikai, but they don’t appear in the top 10 spots on our list. In fact, there are only six Oahu properties on the entire list. When it comes to outrageous real estate, it’s all about the Big Island, where you’ll find nine of the 10 most expensive homes in Hawaii, all strung along the Kona Coast.

We assembled a similar list in 2005, limited to the City and County of Honolulu. Expanding the scope to all of Hawaii has raised the stakes considerably: While the top property in 2005 was assessed at $15.2 million, that number wouldn’t even get you on the bottom rung of this year’s list. The bar starts at $16 million and goes up from there.

The dollar amount listed for each house is the county’s most recent assessment of its value, for tax purposes. In most cases, the property details are also based on publicly available city and county data. One note: We restricted this list to single parcels as defined by the county tax offices. That kept things simple, but meant overlooking a few fabulous estates that comprise multiple parcels, such as the 174-acre Tara Plantation on Kauai, which sold in 2009 for $28 million.

Photo: David Croxford

NO. 1

$61.8 million

7 bedrooms • 7 full and 5 half bathrooms • 18,500-square-foot interior • 189,704-square-foot lot

It’s known as the Raptor Residence, but the man behind this luxurious oceanfront estate is Michael Dell, the founder and CEO of Dell Inc. This year, Forbes ranked Michael Dell as the 37th richest person in the world, with a net worth of $13.5 billion. Hawaii County assesses the house alone at $28.5 million, but the better part of the $61 million valuation of this property is the land itself. It’s lot 1A, the premier parcel in the private, luxury residential community of Kukio. (There are no lots 2 and 3—Dell combined three 1-acre parcels.) Kukio is a relatively recent development, an even more exclusive successor to the already spectacular Hualalai resort, next door, but it already figures prominently on this list. Seven of the 25 most expensive homes in the state are located within one of the three divisions of this Kona Coast oasis.

Photo: David Croxford

NO. 2

$39.4 million

11 bedrooms • 12 full and 3 half bathrooms • 16,023-square-foot interior • 220,414 square-foot lot

Property ownership  is public information, but many of the billionaires and millionaires on our list have set up walls of privacy between themselves and the tax records. The No. 2 most expensive house, for example, is officially owned by Kukio Limited. The Dallas address listed for the tax bill, however, is the same as for Kitano Capital, which was incorporated by financier Ellis Short in 2007. Short has been reported to be an extremely private person; he’s managed to stay largely out of the spotlight as the president of Lone Star Funds, a global investment firm that manages private equity funds worth $24 billion, but not as owner of Sunderland A.F.C., a soccer team in England.


Photo: David Croxford

NO. 3

$31.3 million

5 bedrooms • 7 full and 2 half bathrooms • 12,620-square-foot interior • 117,046-square-foot lot

This oceanfront Kukio property grabs the No. 3 spot even though it sits in the middle of acres of black lava rock in Kona; the luxury subdivision and golf course that will eventually surround it have yet to be built. It belongs to Carol Ann Bartz, the president and CEO of Internet service company Yahoo! Bartz has a long tech pedigree: When she purchased the property in 2006, she was working as president and CEO of Autodesk, a design software company, and has also worked at Sun Microsystems and Digital Equipment Corp. 

Photo: Ryan Siphers

NO. 4

$29.3 million

8 bedrooms • 8 full and 2 half bathrooms • 21,692-square-foot interior • 38,028-square-foot lot

This Wailea house,  the most expensive residential property on Maui, and one of three houses on our list within a 2-mile stretch of coastline, is owned by Thom Weisel, a financier who founded the San Francisco-based investment banking firm Thomas Weisel Partners Group. Weisel has been described by the San Francisco Chronicle as “the alpha male of Wall Street West” with an “uber-competitive streak.” It’s a drive that extends to athletic pursuits, as well. Weisel is a three-time world masters cycling champion.


Photo: David Croxford

NO. 5

$28.8 million

16 bedrooms • 17 full and 3 half bathrooms • 15,614-square-foot interior • 204,732-square-foot lot

The owner of this lavish Kona estate is, to our knowledge, the only one to have owned two of the houses on this list (even if it wasn’t simultaneously). John W. Hoffee II is the retired founder of Temecula, California-based Professional Hospital Supply.  He started the company in 1981 and it’s today headed up by his daughter, Jenise Luttgens. He sold his mansion on the Bluffs of Mauna Kea (No. 13) in order to move a few miles down the coast to one of Kukio’s newer developments.

Photo: David Croxford

NO. 6

$25.4 million

5 bedrooms • 5 full and 1 half bathrooms • 7,938-square-foot interior • 59,764-square-foot lot

Just two lots down from Michael Dell’s sprawling Kukio estate is another multi-structure compound, this one belonging to David L. Anderson, the managing director of Sutter Hill Ventures. Under his management, the venture-capital company has invested, quite successfully, in tech-based startups; its portfolio includes a grab bag of up-and-comers in software, healthcare and computer technology. As valuable as the oceanfront property is, the five-bedroom house is worth even more—$14 million of pure luxury.


Photo: David Croxford

NO. 7

$23.1 million

4 bedrooms • 4 full and 2 half bathrooms • 6,804-square-foot interior • 63,978-square-foot lot

More than half of the top 25 homes in Hawaii are located on the Kona Coast, and they’re all in private resort communities—Kukio, Mauna Lani, Mauna Kea and Hualalai. This property happens to be the most expensive parcel in Hualalai, and looks out onto the greens of the exclusive Hualalai golf course. It’s owned by Helen and Charles Schwab. Yes, that Schwab—founder and chairman of the Charles Schwab Corp., and ranked by Forbes as the 50th richest person in the U.S., with a fortune totaling approximately $4.7 billion.

Photo: David Croxford

NO. 8

$23.1 million

6 bedrooms • 7 full and 2 half bathrooms • 9,525-square-foot interior • 48,439-square-foot lot

This house looks  out onto Kukio’s South Pond, and then onto the ocean. (Although when we flew over the property, the pond was all but empty. Maintaining water features in arid Kona can’t be easy.) The owner is yet another investment banker: Paul Stephens, the chairman and a partner of Stephens Investment Management, and the co-founder and managing director of RS Investments, a San Francisco-based management group that manages more than $7 billion in assets.


Photo: David Croxford

NO. 9

$22 million

3 bedrooms • 4 full and 2 half bathrooms • 5,548-square-foot interior • 65,723-square-foot lot

As pricey as they are, many of the other properties on our list are squeezed right next to other mansions. This stunning property, though, sits all by itself on the point of Hualalai, with a panoramic ocean view. It’s owned by George R. Roberts, the co-founder of a global leveraged buyout firm called Kohlberg Kravis Roberts & Co. (For an idea of how the business works, check out the 1990 book, later made into a movie, detailing his firm’s leveraged buyout of RJR Nabisco, entitled Barbarians at the Gate.) Buyouts have been good for Roberts: Forbes ranked him No. 85 on its 2009 list of the 400 richest Americans, with a net worth of $3.5 billion.

Photo: David Croxford

NO. 10

$21.9 million

7 bedrooms • 8 full and 3 half bathrooms • 14,680-square-foot interior • 68,825-square-foot lot

This diamond of a property belongs to Bandel and Paula Carano. Carano has been a heavy hitter in the venture-capital scene since the 1980s, when he became partner at Oak Investment Partners. These days, he’s also on the board of directors of Kratos, a federal defense and security contractor, as well as a laundry list of other public and private corporations. Carano’s Kukio house may look compact compared with many of the other Kona estates, but it packs a lot into the more-than- 14,000-square-foot interior: the house is valued at $18.2 million, almost five times as much as the land on which it sits.


Photo: Karl Hedberg

NO. 11

$21 million 

5 bedrooms • 7 full and 2 half bathrooms • 9,896-square-foot interior • 56,510-square-foot lot

Japanese corporation  Mint Yugen Gaisha picked this one up for $29 million in 2006, making it one of Hawaii’s largest residential sales of the past decade. Originally built by former Kahala Hilton owner William Weinberg in 1988, the single-story Kahala home has the best of everything: it even had an underground gasoline tank installed in the front yard, so one can fuel cars right in the garage.

Photo: Karl Hedberg

NO. 12

$20.9 million 

5 bedrooms • 7 bathrooms • 10,706-square-foot interior • 93,706-square-foot lot

This Vladimir Ossipoff-designed home  is best known as the long-time residence of socialite Clare Boothe Luce, wife of noted magazine publisher Henry R. Luce. The home is now owned by Houston-based Fayez Sarofim. Sarofim, an Egyptian-born money manager who is known as “the Sphinx,” bought the house in 1999 for $15 million, and has since made extensive renovations to the aging Kahala Avenue property.


Photo: David Croxford

NO. 13

$20.6 million 

10 bedrooms • 10 bathrooms • 17,000-square-foot interior • 108,726-square-foot lot

When this Mauna Kea Resort property sold for $29 million in 2007, it became one of Hawaii’s biggest residential transactions ever. Richard Rocker, the real estate agent who brokered the sale, says, “I see a lot of fancy, expensive homes, and so many of them are just expensive. This one is really well done. Not only is the lot 2.5 acres, there are 2.5 acres of conservation land in front, and another 3 acres of resort common area in back. You get 8 acres of privacy in the middle of a resort. Nobody has this.” The property is officially owned by Palekaiko Limited Partnership, the Montreal office of which is the same as the headquarters of Cirque du Soleil. Guy Laliberte, the founder of the internationally known circus, is worth $2.5 billion, according to Forbes’ most recent list of the world’s billionaires.


NO. 14

$20 million

9 bedrooms • 9 bathrooms • 10,211-square-foot interior • 57,861-square-foot lot

Overlooking the water just across the bay from the Mauna Lani Resort, this wedge-shaped Kona property belongs to Toyota Motor Sales USA. It’s one of the older houses on our list, built in 1992, but has kept its value admirably, with an assessment of $14.7 million. There’s room for expansion, too; Toyota also owns the adjacent lot, which is assessed at $4.7 million. May we suggest a car dealership?


Photo: David Croxford

NO. 15

$19.4 million

6 bedrooms • 7 full and 2 half bathrooms • 9,821-square-foot interior • 217,843-square-foot lot

This huge, 5-acre estate is the farthest north of all our Kona Coast properties—it’s on the edge of the Mauna Kea Resort, next door to the old Lurline Roth estate. It’s owned by Hale O Aloha, which shares a mailing address with SalesForce Inc., a cloud-computing software company founded by Marc Benioff, a 30-year-veteran of the software industry. The publicly traded SalesForce has been lauded as one of BusinessWeek’s Top 100 Most Innovative Companies.

Photo: Karl Hedberg

NO. 16

$19.3 million

11 bedrooms • 9 full and one half bathrooms • 17,408-square-foot interior • 55,937-square-foot lot

This is one of the few properties on our list that sold for less than its assessed value. Chikako Takeda scored this Kahala Avenue monster for a thrifty $9.7 million in 2002. She got a lot for her money; although you can’t see it in the photo, the house is twice as long as it is wide. Think of it this way: This 17,408-square-foot interior is almost half an acre of house. The land is currently valued at $14.3 million.


Photo: Karl Hedberg

NO. 17

$19.2 million

7 bedrooms • 8 full and 1 half bathrooms • 11,216-square-foot interior • 62,870-square-foot lot

Honolulu attorney David Schutter spared no expense in constructing this Kahala Avenue mansion in the 1980s. He packed his home with amenities—Jacuzzis, two pools, waterfalls, a billiards room, and invited over celebs such as Kareem Abdul Jabar and Lionel Ritchie. Real estate agent Jeffrey Fox brokered the 1997 sale to its current owner, Kirin Planning. “Schutter was the kind of guy who would drive around town in a Rolls Royce convertible with the license plate ‘Sue Em.’”

Photo: Karl Hedberg

NO. 18

$18.2 million

8 bedrooms • 9 full and 9 half bathrooms • 20,094-square-foot interior • 42,175-square-foot lot

How things have changed.  When we rounded up the 25 most expensive homes on Oahu in 2005, this Kahala house topped the list. This time, it’s not even the most expensive Kahala property. The place remains impressive, though. The man behind the masterpiece is architect Roy K. Yamamoto, whose work includes the Westin Maui and Hilton Waikoloa. Homeowner Tomomi Kimura, chairman of a Tokyo-based shipping company, commissioned the house in 1992, the same year the summer Olympics were held in Barcelona. “[The owner] wanted the design to reflect that Barcelona style,” recalled Yamamoto when HONOLULU interviewed him in 2005. The sprawling mansion also includes a spa, tatami room and commercial-grade kitchen that’s “five times bigger than a lot of restaurants in town,” says Yamamoto.


Photo: David Croxford

NO. 19

$18.1 million 

5 bedrooms • 5 full and 1 half bathrooms • 6,329-square-foot interior • 49,136-square-foot lot

Who needs to swim  in the ocean when you’ve got a pool this gargantuan? Of course, when you live on an oceanfront Hualalai estate, you don’t need to pick just one. It’s owned by H25A LLC, which has its Los Angeles office at the same address as Oaktree Capital Management, chaired by Howard Marks. Oaktree manages $47 billion worth of investments, according to Forbes, putting him in good company with his wealthy neighbors.

Photo: Karl Hedberg

NO. 20

$18 million 

5 bedrooms • 6 full and 1 half bathrooms • 8,359-square-foot interior • 64,295-square-foot lot

If this Kahala Avenue  compound looks like a beachside motel, well, it kind of is. The property is mainly used by owner Konami Corp., the Tokyo-based developer of videogame software, for company get-togethers. Other features include 50-foot-long glass windows, a practice green, a barbecue area and a state-of-the-art audiovisual system, says local architect Toshi Suzuki, who designed the mauka side of the property in 2000.


Photo: Ryan Siphers

NO. 21

$17.1 million 

5 bedrooms • 5 full and 1 half bathrooms • 5,914-square-foot interior

It would be hard to find a more spectacular location for a dream home. Michael G. McCaffery’s $3-million house sits alone out on a point in Makena, surrounded on three sides by ocean. The Maui retreat has obviously inspired McCaffery—the investment management firm of which he is the CEO is called Makena Capital Management.

Photo: Ryan Siphers

NO. 22

$16.7 million 

9 bedrooms • 9 full and 2 half bathrooms • 19,000-square-foot interior • 22,902-square-foot lot

This Wailea property, known as sandy surf, isn’t used as a full-time residence. Owners Charles and Elizabeth Thieriot frequently rent the place out for extravagant vacationers. Guests have included everyone from Prince to Michael Jackson and Mel Gibson. Charles “Kip” Thieriot, now retired, is a member of the prestigious family that founded and ran the San Francisco Chronicle, and was himself the president of Western Communications.


Photo: Ryan Siphers

NO. 23

$16.3 million 

4 bedrooms • 5 full and 2 half bathrooms • 28,261-square-foot lot

Artist Christian Riese Lassen  is known for his paintings of vibrant oceanscapes and sparkling dolphins, and his Kapalua home is inspired by that Technicolor turquoise aesthetic. “We incorporated elements of Christian’s art throughout the house,” says architect Jeff Long. “Just about every room relates to the ocean.” And good news: If you’ve got a spare $6,750, you can spend a night here—Lassen rents it out whenever he’s not there himself.

Photo: David Croxford

NO. 24

$16.3 million

2 bedrooms • 2 full and 2 half bathrooms • 7,936-square-foot interior • 70,480-square-foot lot

This sleek Kona abode belongs to Sandra Kurtzig, who Entrepreneur Magazine called “the first lady of computers.” Kurtzig founded ASK Computer Systems out of her apartment in 1972, selling inventory-tracking and business-information software, and turned her tiny startup into a heavy hitter with 91 offices in 15 countries.


Photo: Ryan Siphers

NO. 25

$16.1 million

4 bedrooms • 5 full and 1 half bathrooms • 11,340-square-foot interior • 30,554-square-foot lot

Talk about ritzy stretches  of beach: This Kapalua mansion is next door to Christian Riese Lassen’s house (No. 23). Here, the land definitely outweighs the house. The .7-acre lot is assessed at $13.3 million. Owner William Kevin O’Neil got his money’s worth, though; Oneloa Beach is one of Maui’s nicest white sand beaches.