The Most Expensive Homes for Sale in Hawaii

Boasting what is probably the highest concentration of breathtaking vistas in the Union, not to mention gorgeous weather and a laid-back lifestyle, Hawaii is a top destination not only for tourism, but for some pretty swanky real estate as well, with the top end of Hawaii’s real estate market featuring some of the most dreamy – and pricey – real estate in the country.

The overall residential buying market in the Aloha State is experiencing very healthy growth numbers at the moment, with the Oahu single-family median sale price hitting a near-record $755,000 in February – just a breath short of the record $760,000 set in June of last year. Condo prices have inched higher too, especially as sales figures saw double-digit increases due to extremely tight inventory in the single-family market, per the Honolulu Board of REALTORS. And it’s not just the densely-populated capital area that’s tearing it up right now – Maui hit the highest median sale price for condos since February 2009 early this year.

Although the luxury section of Hawaii real estate remains a buyer’s market due to overabundance of inventory – with some submarkets sporting up to 17 months of inventory – this is part of an overall nationwide trend reflected in many mainland states such as Florida and Colorado.

Ranging in price from just short of $25 million to a whopping $45 million, the most expensive homes for sale in Hawaii are all about that sweet island life: tropical landscaping, thousands of square feet of laid-back indoor-outdoor living, infinity pools with endless ocean vistas and whale watching from the comfort of your living room – these fabulous pads are all about being on a perpetual paradise getaway.

As for the most expensive home for sale in Hawaii right now, it is an artfully renovated and expanded home that’s an ode to Hawaiiana, with bespoke décor and artwork, ocean and mountain views, four separate residences – oh and a 1,875-square-foot pool!


210 Kalaheo Avenue, Kailua

Asking price:$24,980,000

Touted as “one of Oahu’s most significant beachfront estates,” this 1.5-acre tropical paradise on Kailua Beach has a bit of a celebrity status, having hosted numerous VIPs and Hollywood types in recent years. In fact, the property itself is a celebrity, having been featured on Hawaii Five-0’s Ho’opa’i episode – yes, the one with P.Diddy. Comprising a 5-bed main residence complete with waterfall pool and a 3-bed guest house, the property totals 17,333 square feet of covered living area with lanais abounding.


4000 Wailea Alanui Drive #102, Kihei

Asking price:$25,000,000

Located 40 feet above the water on Maui’s famed Wailea Beach, this 2-bed, 3,850-square-foot Wailea Point condo boasts some of the most fabulous views on the island – you can actually do some whale watching from the comfort of your own home! With almost 30 acres of landscaped grounds, including edible landscaping, and a host of amenities such as pools, entertainment pavilions and tennis courts, residents at the golf-cart-friendly community enjoy a pretty laid-back lifestyle.


69-2012 Nani Paniau Place, Puako

Asking price:$27,500,000

One of the largest privately owned oceanfront compounds on the Kohala Coast, the 7.45-acre park-like estate boasts a swoon-inducing 1,000 feet of ocean frontage, high levels of privacy and easy access to the area’s resorts and retail. The estate consists of 10 parcels, with the largest one holding the 10,000-square-foot, 7-bed residence designed by Lucky Bennett.


3244 S Kihei, Kihei

Asking price:$28,000,000

Located on the southern end of the famed Keawakapu Beach in South Maui, this 9-bed home boasts direct beachfront access while maintaining utter privacy from beachgoers. Totaling 13,422 square feet, the home includes 3 ocean view master suites, penthouse level sundecks, fitness center, pool and garden.


7505 Makena Road, Makena

Asking price:$29,000,000

For those who love outdoor cinemas, this might just be the ultimate dream home with its swanky outdoor theater that rises from the pool deck. Nestled on a 1-acre parcel, the 8-bed residence also offers 10,000 square-feet of indoor-outdoor Hawaiian living with infinite Pacific Ocean views, lush landscaping, water features, close to 4,000 square feet of deck and outdoor furniture, as well as a 6-car garage. But honestly, we’re still stuck on that outdoor theater.


2590 Kauapea Road, Kilauea

Asking price:$29,500,000

Overlooking Kauai’s North Shore – and beyond – from its position above Secret Beach, this 28-acre, four-parcel estate awaits new owners to take its swankiness to the next level. Currently the property holds a 3-bed home with 2,715 square feet of indoor-outdoor living space with a screened-in lanai and 55-foot custom pool with an adjoining hot tub. The estate also features an organic orchard of tropical fruit trees and is convenient for Princeville Airport.


2620-A Kaupea Road, Kilauea

Asking price:$30,000,000

Featuring fantastic views from its vantage point atop a Secret Beach bluff, this 1.45-acre, 4-bed gated property comes with a main home and a guest home, a deeded trail to the beach and a 5-acre perpetual use easement on an adjacent property. On the market furnished, the property features a pool, spa and “one of the largest continuous glass windows in the State of Hawaii” to better enjoy the property’s spectacular whale and dolphin watching possibilities.


4200 Anini Vista Drive, Kalihiwai

Asking price:$31,000,000

Designed by Stephen Devery & Gary Tobey, this 6-bed stunner seamlessly fuses contemporary island design with traditional Hawaiian styles to create one of the most iconic properties on Kauai – and possibly Hawaii. Located on the promontory of Kauai’s north shore, the 18,210-square-foot home boasts some of the most enviable views anywhere, with ocean, mountain and reef vistas easily enjoyed thanks to the use of oversized windows and glass walls in the home’s design. With a 50,000-gallon salt water pool, temperature-controlled wine cellar, 1-bed guest cottage, executive home office, 1,085-square-foot gym and 10,640-watt solar array just a few of this pad’s swanky amenities, it’s no wonder it’s one of Hawaii’s most expensive homes for sale right now.


1118 Ala Moana Boulevard #GPH 35, Honolulu

Asking price:$35,000,000

One of only two grand penthouses at the ultra-luxurious Waiea development, this 8,532-square-foot condo is perched on the 35th floor, offering highly coveted 360-degree views of Waikiki, Diamond Head, the Pacific Ocean and mountains. The 6-bed home boasts a fabulous 2,000-square-foot lanai with ocean-facing infinity pool and comes with a design credit for home customization. Owners will enjoy access to Waiea’s exclusive amenities such as the landscaped 7th floor amenity deck complete with dog park.


1118 Ala Moana Boulevard #GPH 36, Honolulu

Asking price:$36,000,000

The second grand penthouse at Waiea, this 5-bed condo is the epitome of Hawaii high-rise luxury living with its private rooftop infinity pool, sky lanai with outdoor kitchen, 360-degree views of Waikiki, Diamond Head, the Pacific Ocean and mountains, and 4-car garage. Waiea is the flagship building of the 60-acre Ward Village, the only LEED Platinum-certified neighborhood in Hawaii and the largest one in the U.S.


5418 Weke Road, Hanalei

Asking price:$45,000,000

Oozing old Hawaii charm, this 2.5-acre compound on surfers’ paradise Hanalei Beach is a unique 9-bed, multi-property estate totaling 14,720 square feet of fully restored living space enriched with bespoke furniture and décor as well as carefully curated artwork. The family compound includes a 5-bed main residence boasting both ocean and mountain views, a 2-bed beachfront home and 1-bed studio available for purchase separately for a cool $35 million. In addition, you can get a 2-bedroom pool cottage  with a 1,875-square-foot pool and 2,387 square feet of decking for those who’d rather go big and own the entire $45 million estate.

This article was updated on 04/10/2017 to include the listing for 4200 Anini Vista Drive.

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Eliza Theiss

Eliza Theiss

Eliza Theiss is a senior writer reporting real estate trends in the US. Her work has been cited by CBS News, Curbed, The Los Angeles Times, and Forbes among others. With an academic background in journalism, Eliza has been covering real estate since 2012. Before joining PropertyShark, Eliza was an associate editor at Multi-Housing News and Commercial Property Executive. Eliza writes for both PropertyShark and CommercialEdge. Reach her at [email protected]

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