Here are the top 10 Most expensive Homes in Hawaii and who owns them in 2018

If you want to own one of the top expensive homes in Hawaii, it helps to be in computers or investment banking. Using public records collected by Title Guaranty Hawaii, Top Most 10 compiled a list of Hawaii’s expensive 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-10 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.

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.


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.


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.


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.


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.


5. Kona estate $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.


4. Wailea House $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.


3. Oceanfront Kukio Property $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.


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.


1. Raptor Residence $61.8 million- 7 bedrooms • 7 full and 5 half bathrooms • 18,500-square-foot interior • 189,704-square-foot lot

Here are the top 10 Most expensive Homes in Hawaii and who owns them in 2018

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.