The $30 Million Club: Oahu’s Priciest Real Estate, Part 2

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Vistas Abound on Legendary Round Top Drive

In the last installment, we saw what $20 million would buy on the Hawaiian island of Oahu. Let’s head for the sky with the top three priciest residential listings in the $30+ million club. This trio represents the perfect combination of vacant land, condo and estate. One even has a teeny-tiny Dallas connection (not to me – unfortunately!).

Our first property is up in the hills …

3711 Round Top Dr., Honolulu


Round Top Drive is a mythical street in Honolulu. It forms a pearl necklace of homes stretching above the Tantalus area of Honolulu. This home, listed by Sachiyo Braden of Sachi HI Pacific Century Properties is mid-way up with jaw-dropping views stretching from Diamond Head to downtown and the Pacific Ocean beyond. You really feel on top of the island – because you are.


Built in 1990, this 5,289 square foot home featuring 6 bedrooms with 4 full and one half bathrooms is beginning to show its age. The right buyer will almost certainly refresh the property with the requisite kitchen and bathroom re-dos. Listed at $30 million, this home is all about views, location and the pinch over 2-acres this home rests on – the things that can’t be “refreshed.”


The home uses windows to bring in light as well as foster a desire to gape at the views. Another plus to being up-country is the relative coolness and breezes during increasingly warm summers.


Of course beating the heat on a 2,036 square foot lanai with a pool this size doesn’t hurt either! A breakfast of burnt eggs or a happy hour of flat champagne would still taste spectacular from this lanai!


1288 Ala Moana Blvd #PH-B, Honolulu


In a city filled (and being filled) with luxury high-rises, this penthouse at the Hokua building, listed by Patricia Choi of Choi International, is a stunner. With a location sandwiched between two shopping centers and the Howard Hughes Ward Center development, this building is in the thick of things.


At 5,576 square feet containing 4 bedrooms with three full and 1 half bathrooms, this is far from the largest home on this list, but it’s certainly the highest this close to the ocean. Listed at $35,888,000, the second most expensive property listed on Oahu, it proves once again that living off the ground isn’t inexpensive.


There are a lot of reasons to part with $35-extra-extra-large for a home, and this bathroom sums it up. Could you imagine starting your day showering here, completely starkers as the sum rises over Diamond Head? Perhaps taking a bath as the sun sets between your rim-hugging toes? Need a little more water? This two-story penthouse has a rooftop Jacuzzi as part of a 2,800 square foot entertainment aerie.


The building has the amenities you’d expect in such a building. This unit also comes furnished, although at $35-mil, a buyer would likely bring their own designer no matter how nice I think the current décor is.


4423 Kahala Ave., Honolulu


The most expensive property on Oahu has a story. A big, fat, juicy story with a small thread connected to Dallas. First of all, it’s not a home, it’s 2.7 acres of vacant land with an asking price of $48 million.

It’s most recent owner was Japanese billionaire Genshiro Kawamoto who’s often described as “eccentric” which is rich-ese for crazy. In the 1980s he snapped up hundreds of homes and condos in California and Hawaii with “pocket change.” In the 1990s he evicted his tenants with so little notice that California changed their tenant’s rights laws.


In the 2000s, he bought up a bunch of homes in Kahala (the “Old Preston Hollow” of Honolulu) and proceeded to let them fall apart. In some cases he purposely damaged the properties to create eyesores – filling in swimming pools with rubble, boarding up windows and installing tawdry statuary everywhere. He’s been accused of dilapidating neighborhoods in order to snap up more when prices dropped.

Overlying much of his rhetoric was a stated desire to provide low-income housing – promises, at least in Hawaii, that never materialized. He rented multi-million dollar properties to homeless tenants for nothing, letting them fall apart and the tenants run wild with parties likely meant to disrupt the neighborhood.

In Kahala, on Kahala Avenue, it’s safe to say he was reviled.

In March 2014, Japanese prosecutors charged him with tax evasion, revoking his passport. While out on bail, he cut a deal to offload nearly all his Kahala holdings to real estate firm Alexander & Baldwin. Champagne corks likely deafened the streets of Kahala. Not part of that original deal were the three adjoining parcels listed here by his long-time Realtor Patricia Choi.

Oh, the Dallas connection? Choi was in Dallas in September meeting with Allie Beth Allman for some second-home cross pollination as part of a tour with Christies. I’m guessing that it was in between Berkshire Hathaway negotiations that Allman gave Choi a tour of the most expensive home in Dallas, Walnut Place.

Now’s your chance to own some of the most infamous dirt on Oahu in many years … for $48 million.

Remember: Do you have a location you’d like to see featured?  I travel quite a bit and enjoy poking around real estate.  Realtors, have clients who’d like to document their second home journey?  Shoot Jon an email. Marriage proposals accepted (they’re legal)!