The Most Expensive Houses in Hawaii

March 9, 2023

most expensive houses in Hawaii

If you are looking to buy a house in Hawaii, you might be wondering which are the most expensive houses available on the island. That is because Hawaii is one of the most expensive places to live in the world.

Its cost of living index is more than 30% higher than the US average. But if you know where to look, you can find homes that are much more affordable than others.

1. Hale Palekaiko – House of Paradise

If you’re looking for a house that offers sweeping ocean views and plenty of space, Hale Palekaiko – House of Paradise is the place to be. Completed last year, this indo-modern home has a main villa, a guest house and a poolside bar.

Located on Kailua Beach, this property is currently for sale through Coldwell Banker Pacific Properties and could be yours for $22.8 million.

The home features a spacious main villa and guest house with 11,476 square feet of interior space. It also has a pavilion for outdoor entertainment, an outdoor kitchen area with barbecue and pizza oven, a spa bathroom and a fully-finished 4-car luxury garage.

It’s the perfect retreat for families and entertainers alike. Designed by award-winning architect Peter Vincent, this residence blends indoor and outdoor living spaces.

2. Hualalai Estate – The Billionaire’s Paradise

Hualalai is one of Hawaii’s most exclusive residential communities. Located on the exclusive Kona-Kohala coast of the Big Island, this resort boasts an array of amenities and is surrounded by natural beauty.

Billionaires from around the world are attracted to this community because of its luxury amenities, family-friendly environment and a rich Hawaiian culture. Oprah Winfrey owns a property here, while eBay founder Pierre Omidyar has a home in Kukio, another Hualalai development on the northern tip of the Big Island.

Owning a home at Hualalai is no small feat, and requires extensive planning, research and preparation to make sure that the investment is worth the money. Luckily, for those who are not wealthy enough to own an estate in the state, a variety of Hualalai condos are available to suit every budget. These units are typically single story homes that are either attached to a larger condo or in clusters of three. They are also equipped with a private pool and spa.

3. Kahala Beach House – The Billionaire’s Paradise

Billionaires and business moguls have long been drawn to Kahala, an upscale neighborhood of oceanfront mansions along the eastern coast of Oahu. The affluent community is known for its pristine beaches, coconut palms and exclusive beachfront properties.

There are also a number of parks in the area, which are often used for gatherings and sports. They’re a testament to the high demand for park space in the area and its residents’ desire for a place to unwind with their loved ones.

The neighborhood is home to a variety of restaurants, including a Michelin-starred Italian restaurant and an open-air, beachfront eatery that serves a modern spin on Hawaiian cuisine. There are also several shopping options and a number of excellent schools in the area.

4. Black Point – The Billionaire’s Paradise

Located in the tiny town of Prouts Neck, Black Point is the hotel of choice for those looking to take in some of the area's finest golf. The hotel is home to a fine collection of guest rooms and suites, a handful of restaurants, a full-service spa and wellness center and one of the area's best golf courses. This upscale property also happens to be the most expensive of its kind, which is why it's a good idea to book well in advance if you want to avoid the dreaded waitlist and other hassles that go along with waiting for the big day to arrive.

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