Oahu Edition

Looking for the most grandiose, opulent, expensive real estate in Honolulu? Look no further. We've gathered a collection of the most expensive penthouses in paradise for your guilty pleasure. All of the following are active listings and waiting for its next millionaire owner to call home.

(All photos are courtesy of the MLS and prices are as of 4/8/19.)

One Waterfront Tower #4502


This 3-story 4,475 sf Kakaako penthouse was sits atop the 45th story of One Waterfront Tower. The 2 bedroom floor plan is customizable and can allow up to 5 bedrooms with 2 full bathrooms and 1 half bath. Features include private elevator entrance, a fully authentic Japanese Tatami Tea room & panoramic 270-degree Diamond Head, Ocean, Harbor & Ko'olau views. Don't forget the multiple entertainment rooms for all your envious friends.

Imperial Plaza #3901


Completely remodeled in 2007, this 2-story penthouse sits on the 39th floor of Imperial Plaza in Kakaako. 3 bedroom, 3 bathrooms, 3 parking stalls and over 3,800 of interior square footage. $4.6M price tag but the seller is open to "any reasonable offer", so get your checkbooks open. 

One Ala Moana #2301


The 23rd story Grand Penthouse at One Ala Moana features 3,669 SF of interior space and a whopping 2,108 SF of private outdoor lanai space including a jacuzzi of course. The interior space features 10 foot high ceilings, a 210 bottle Sub-Zero wine cooler with a Den and Entertainment room. The breathtaking views from the floor-to-ceiling glass are not too bad either.  

The Pinnacle #PH


The Pinnacle is a lesser known building in downtown Honolulu which has one of the more unique penthouses on the market. It is the only penthouse unit in the building and covers 2 stories (35 & 36). If 2 stories is not enough, there is an option to purchase the 34th story unit for an additional $2M for a total of $7.95M. The penthouse has a full 360 degree view including Ocean, Pearl Harbor, Diamond Head and Waikiki. The interior furnishings cost $2M (Casa Fendi) and includes four garage parking spaces. If you consider the original sales price was $16.8M, then $5.8M might be considered a steal.

3019 Kalakau Ave #8


Sometimes you just crave those ocean views. There hasn't been any land to put up condos in Honolulu's waterfront for a very long time and there probably wont ever be again. Built in 1961, this isn't the flashiest of buildings, however it gets a spot on our list simply for the fact that the views are truly unbelievable. This unit underwent a $1.2M renovation in 2012 and features 2 bedrooms, 2 bathrooms and 2,500 SF of interior and lanai space. Was the renovation worth it? Well it made Architectural Digest Top 100 list, so they seem to think so. See for yourself.

Tahitienne Inc #PH


This is another lesser known ocean front condo located in the gold coast of Waikiki. Built in 1957 and renovated in 2008, this home commands a huge price tag because there's very little like it. The sleek, modern, contemporary design was designed by the ID group of Los Angeles and is our favorite interior on the list. This 3 bed, 3 bath penthouse comes with 2,800 SF of interior space and 645 SF of lanai space to soak in those breathtaking ocean front views. 

Waiea #3600


This is it, the Big Kahuna. The most expensive and largest penthouse in all of Honolulu history. Billed the "Estate in the Sky", the Grand Penthouse of Waiea (one of the newest ultra-luxury condo's by Howard Hughes development) is priced at a whopping $36,000,000. It features 5 bedrooms, 5 bathrooms, 10,103 interior SF and 1,570 SF of outdoor lanai space. In addition you get a private rooftop infinity pool/spa, wine room, media room and a private garage. Located in the heart of the Ward Village master plan, you are steps away from restaurants, Whole Foods, and Ala Moana Beach Park - but you probably would never leave this place. The maintenance fee comes in at $12,106 per month and the property tax totals $24,853 a month. That's a total of $36,959 a month in ownership costs! But then again, if you have $36M to spare on a home, that's probably not your biggest concern. Check it out:

If you are interested in learning more about Honolulu real estate, please visit our Condo Guide or Search Tool.


Isaiah Block is an experienced realtor who can help you navigate the process of buying or selling real estate here in Oahu. If you'd like to get in touch directly, please send an email to isaiah@condokakaako.com