The $20 Million Club: Oahu’s Priciest Real Estate, Part 1

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5403 Kalanianaole Highway; $20 mil and gorgeous.

With a median home price of $720,000, it’s not difficult to find pearl-clutching real estate in Hawaii. In fact, as of this writing, Oahu has 10 properties listed above $20 million with three above $30 million. By comparison, not counting hip pockets and new high-rise penthouses, Dallas has just two properties above $20 million (Both Allie Beth, so I guess Berkshire knew what they were doing) not counting the perennially ex-directory Crespi-Hicks-Walnut Place estate.

Let’s pretend our Megamillions ticket was a winner. Let’s start from the “bottom” with a pair of $20 mils.

1133 Ikena Circle, Honolulu


Listed with Sachiyo Braden of Hawai’i Pacific Century Properties, this 9,570-square-foot estate is located high up on Hawai’i Loa Ridge, one of several mountain ridges covered in homes. The property features four bedrooms with five full and two half baths. Built in 1996, this home is all about location. Situated near the top of the ridge, it has views from everywhere to everywhere. If a Western buyer were found (less likely in my opinion) they would likely redecorate to suit a less 1996, imitation French style. The more likely scenario sees an Asian buyer leaving it as is.


The home’s exterior is typical Hawai’i stucco luxury with a mix of styles whose chief purpose is to impress those equating Western traditional décor with wealth – even in the tropics. The central staircase shouts California-French a whole lot louder than Hawai’i. It’s a home for someone happier being somewhere else.


Were this home in Dallas, renovation would begin immediately with no one missing the sea of petticoat drapes lining most rooms.


But nit-picking aside, the reason to purchase this home is the view – just remember the grocery store is likely a long winding 30-minute drive down the hill. All the rest can be fixed with a sledgehammer and a paint brush.

But personally for $20 mil, I’d want renovation to be a more difficult choice to make. Unfortunately, I don’t believe the listing agent was being ironic when she wrote the home, “is designed in the 18th century French style rarely seen today.” Thank God!


5403 Kalanianaole Highway


Next up is the beach house you’d want to pay $20 mil for. Located on Niu Beach in the Aina Haina area of Honolulu this home has 185 feet of ocean frontage – this is where lust begins. Marketed by Tracy Allen from Coldwell Banker Pacific Properties, this freshly remodeled home has eight bedrooms, eight full baths and one half bath within its 11,940 square feet.

The home is cleverly placed near the rear of the property and situated to maximize the ocean. There are gardens and a tennis court in between the road and the home to dull any traffic noise.   And let’s face it, with the ocean as your backyard, that’s where you want to be, right?


As the patter goes, this remodel is so fresh the paint’s not dry. A very quality renovation was done too that’s perfect for today’s living needs (if you need nearly 12,000 square feet).


I’m loving the central hub of a kitchen with all the whiz-bang and preparation area and gadgetry I’d love (including a big ol’ wine fridge!). While the kitchen doesn’t have the cliché window over the kitchen sink, the views of the ocean are stunning through the wall of sliding windows. And besides, at $20 mil, I expect I wouldn’t be the one cleaning up!


The master bath is probably the size of our first apartments, but whew! It surely ticks every box I can think of (and a few I probably forgot).

I won’t bore you with more pictures of wonderful décor and unending ocean views. But I have to ask, who’d want a French mausoleum in the mountains over an oceanfront stunner like this?


123 Kailuana Loop, Kailua


Want to share the beach with Obama during his annual holiday visits to the islands? This Kailua beachfront beauty may be the answer. Listed by Patricia Choi of Choi International for $20,138,000, this 8,182-square-foot home has 7 bedrooms with 9 full and 2 half baths. It sits on 0.7 of an acre with 125 feet of ocean frontage on Kailua beach.


The interior is stunning with a kitchen that showcases the quality of this home’s interior. No expense was spared with Wolf ovens and Sub Zero refrigeration surrounded by custom cabinetry.


Imagine waking up to this view? Would you ever leave the bed? I know I wouldn’t! Vaulted and beamed ceilings and a wall of windows supplying fresh ocean air. Ahhh!


In the center courtyard of this U-shaped home is a resort-like pool with a hot tub and waterfall. For those buyers with mobility issues, there’s even an elevator. In addition to all this luxury, this 2012 home is LEED GOLD certified.


3159 Puu Paka Dr


Want to get away from it all in paradise? Here’s 46 acres consisting of 9 tracts, freshly on the market. Located literally at the end of the road in the Dowsett Highlands (on a ridge) with views of Honolulu and the ocean. It’s located off the Pali Highway in the pricey Nuuanu-Punchbowl area. If peace appeals to your deep pockets, jot Holden Lau a note at Locations LLC.. It abuts conservation land which should keep neighbors to a minimum. Zoned residential, you can build whatever palace or palaces you’d like. The price for this scale of privacy? A cool $22 million.


72 S Kalaheo Ave, Kailua


Back to Kailua for this oceanfront new build beauty with views of the twin Mokulua Islands. This 8,348-square-foot home, listed with Anne Oliver from Coldwell Banker has 7 bedrooms with 8 full and 2 half baths spread fairly equally between the main and guest residences connected by an outdoor pavilion. It sits on a long, narrow 0.8 acres and is available for $22.8 million. This home makes the most of its setting with pavilions surrounding various water features.


For me if you want to know the quality of a new-build, look at the kitchen and bathrooms. The kitchen in this beachfront estate is just what you’d expect – gorgeous.


The master bathroom is as large and lux as you’d want for $22.8mil. Lots of marble and crystal with a walk-in closet you could camp out in.


Hawaii is big on outdoor living and this home begs owners to get out of the house (not an easy task) with this outdoor pavilion with kitchen. It’s the perfect place for owners and guests to meet between the two sections of the home.


59 & 63 Kailuana Pl., Kailua


Located at the far end of the Kailua Beach “hook” near the Marine base known as K-Bay (short for Kane’ohe Bay – the bay on the backside of the base). This five-year-old home, listed with Judith Whitfield of Sotheby’s sits on 1.25 acres with 200 linear feet of ocean frontage. It has 5-bedrooms, 6 full and 1 half bathrooms contained in 6,452 square feet listed at $23 million.


All the major rooms face the bay backwards towards land. This makes for better night views. You see, looking straight out towards the ocean is great during the day, but at night it’s just inky blackness. This home captures the coastline offering more visual interest at all hours.


For a new home, everything is still fresh with a major kitchen with custom tropical wood cabinets, granite and tippy-top of the line appliances including a walk-in wine cellar..

Outdoors has all the requisite fountains, fire pits, tiki torches, spa and barbeque a buyer would expect in paradise. It’s been on the market for over a year, so sharpen your bargaining pencils.


61-779 Papailoa Rd., Haleiwa


Popping up to the North Shore of Oahu, we see this $25 million gem listed by Michael Shower of Coldwell Banker on a wide sandy beach. Situated on a half-acre, this 5,646-square-foot home has 5 bedrooms, 6 full and 1 half bathrooms. The home also sports an additional 1,471 square feet of outdoor living space and a spa pool.


And what a lanai it is, just a pineapple’s throw from the waves and perfect for entertaining the best of friends.


That’s what this home was built for – entertaining – as this oceanfront kitchen and dining area attest to. An eight-barstool island is perfect for the host/cook who puts food preparation center stage with the views.


The home is a well-executed mixture of Polynesian and modern design. Everything is top of the line for today’s multi-hundred-millionaires. The rest of the home is equally drool-worthy and you can see more pics by clicking the address links for each of these properties.

That rounds up the seven members of the $20 Million Club. Stay tuned for my next installment … The $30-Plus Million Club.


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)!