Oahu's Top 10 Most Expensive Homes

Oahu boasts some of the world's finest homes--and some of the world's heftiest home prices. We've rounded up the top 10 most expensive homes currently for sale in Honolulu so you can see how the ultra-rich and famous live. Hey, it doesn't hurt to dream, right?

NUMBER ONE

1118 Ala Moana Boulevard, GPH 36, Honolulu | MLS #:201612214

$36,000,000

• 5 bedrooms 
• 5 full baths 
• 1 half baths 
• 10,076 sqft 

The most expensive home currently for sale on Oahu sits atop 36-floor luxury high-rise condo building, Waiea ("water of life") in the booming Kakaako neighborhood. This 10,000-sqft grand penthouse is the ultimate in luxury living. Designed by award-winning architect James K.M. Cheng & WCIT Architecture, along with internationally acclaimed interior designer Tony Ingrao, this home rivals the great penthouses across the globe. Waiea represents a new level of luxury in Hawaii and is the flagship building of Honolulu’s most distinguished urban neighborhood, Ward Village in Kakaako. This home features a private elevator, unsurpassed 360-degree views, a private rooftop infinity pool, sky lanai with outdoor kitchen and pool house, and 4-car garage. On top of its whopping $36 million-dollar price tag, buyers should be prepared to shell out $11,100 a month in maintenance fees. 

Property listed by Hawaii Life Real Est. Brokers.

NUMBER TWO

1118 Ala Moana Boulevard, GPH 35, Honolulu | MLS #:201629077

$35,000,000

• 6 bedrooms 
• 6 full baths 
• 1 half baths 
• 8,485 sqft 

The second-most expensive home on the market is also a penthouse in the Waiea building. Located on the 35th floor and only slightly smaller than the building's grand penthouse, this $35 million dollar home comes with a design credit for the new owners to fully customize the home with their choice of interior design finishes. The home also includes a 2,000-sqft rooftop lanai with private ocean-facing infinity pool and perpetual 360-degree views of the Pacific Ocean, Diamond Head, mountains and Waikiki.

Property listed by List Sotheby'S Int'L Realty.

NUMBER THREE

51 Kaikea Place, Kailua 96734 | MLS #:201715306

$26,000,000

• 7 bedrooms 
• 5 full baths 
• 2 half baths 
• 7,851 sqft 
• Land Area: 89,923 sqft

The most expensive single-family home currently for sale on Oahu sits on 2 acres of enviable oceanfront land fronting Kailua Bay in the Beachside neighborhood. This resort-like property includes a caretaker's cottage and is fully furnished.

Property listed by Aska Estate Hawaii Inc.

NUMBER FOUR

72 Kalaheo Avenue, Kailua 96734 | MLS #:201714646

$22,800,000

• 7 bedrooms 
• 8 full baths 
• 2 half baths 
• 8,348 sqft 
• Land Area: 36,995 sqft

The second most expensive single-family home on our list is also located in the Beachside neighborhood of Kailua and runs from the avenue to the ocean. Dubbed Hale Palekaiko - House of Paradise - this recently completed contemporary tropical estate is designed by award-winning architect Peter Vincent. In addition to the main 4-bedroom, 4.5-bathroom residence, the property also includes a 3-bedroom, 3.5-bathroom guest residence and outdoor entertainment pavilion with poolside bar, kitchen and spa bathroom.

Property listed by Coldwell Banker Pacific Prop.

NUMBER FIVE

202 Kaikuono Place, Honolulu 96816 | MLS #:201714663

$22,00,000

• 4 bedrooms 
• 4 full baths 
• 1 half baths 
• 4,829 sqft 
• Land Area: 8,414 sqft

This elegant multi-level contemporary oceanfront home located near Doris Duke's famed Shangri La Estate boasts some of Honolulu's finest views of an azure cove, coconut-lined white sand beaches, surf, sunsets and, of course, Diamond Head. Featured in Forbes Magazine and Architectural Digest, this intimate home includes private deeded beach access to one of Diamond Head's finest beaches and is close to the shopping and dining of the Waikiki and Kahala nieghborhoods.

Property listed by Hawaii Life Real Est. Brokers.

NUMBER SIX (TIED)

5403 Kalanianaole Highway, Honolulu | MLS #:201628812

$20,00,000

• 8 bedrooms 
• 8 full baths 
• 1 half baths 
• 11,940 sqft 
• Land Area: 62,334 sqft

This modern 1.43-acre oceanfront estate claims 185 linear feet of beach frontage and includes a tennis court, pool and Jacuzzi lush set among lush tropical landscaping. The main home features 7 bedrooms, 3 of which are master suites. The property also includes a seperate caretaker's suite with kitchen. If you love to entertain, this home's expansive, seaside lanais can't be beat!

Property listed by Coldwell Banker Pacific Prop.

NUMBER SIX (TIED)

1133 Ikena Circle, Honolulu | MLS #:201612012

$20,00,000

• 4 bedrooms 
• 5 full baths 
• 2 half baths 
• 9,570 sqft 
• Land Area: 30,855 sqft

Mentioned among Forbes' list of "Incredible Mansions," Hi'ilani ("In the Arms of Heaven") is a one-of-a-kind, 19th-century French-inspired estate designed to capture jaw-dropping ocean and sunset views.

Property listed by Sachi Hi Pacific Century Prop.

NUMBER SEVEN

2332 Makiki Heights Drive Honolulu | MLS #:201627051

$18,000,000

• 8 bedrooms 
• 9 full baths 
• 1 half baths 
• 7,691 sqft 
• Land Area: 112,627 sqft

With two homes sitting atop 2.5 acres in the prestigious Makiki Heights neighborhood, this property offers the largest land area on our list. With a resort-sized infinity pool, spa, sweeping views and close proximity to Downtown and Waikiki, you could make this home your own mini-resort or add additional homes to the site for a palatial family compound or corporate retreat. 

Property listed by Choi International.

NUMBER EIGHT

280 Poipu Drive, Honolulu | MLS #:201622633

$17,750,000

• 6 bedrooms 
• 5 full baths 
• 2 half baths 
• 6,502 sqft 
• Land Area: 21,539 sqft

This Hawaii Kai home, situated in the Triangle neighborhood (adjacent to prestigous Portlock), offers many special touches, including sandstone wall relief features, professional-grade home theater with reclining leather seating for eight, a seperate ohana cottage, water features and many home automation features (including lighting, doors and fans).

Property listed by Oahure.com.

NUMBER NINE

3215 Diamond Head Road, Honolulu | MLS #:201709585

$17,250,000

• 5 bedrooms 
• 5 full baths 
• 1 half baths 
• 4,988 sqft 
• Land Area: 14,248 sqft

One of only 19 homes along this treasured section of Diamond Head Road, this beachfront residence offers nearly 100 feet of linear ocean frontage and is within walking distance to Waikiki. Extensively renovated in 2017, the home includes soaring 20-foot ceilings in the living room and disappearing glass doors that open to the pool, yard and ocean. It also has private stairs to the beach, gated entry, two oceanfront master suites with private lanais, a media room, spa and lush tropical landscaping.

Coldwell Banker Pacific Prop.

NUMBER TEN

5949 Kalanianaole Highway, D, Honolulu | MLS #:201623396

$16,500,000

• 5 bedrooms 
• 6 full baths 
• 7,995 sqft 
• Land Area: 47,737 sqft

Rounding out of top ten most expensive Honolulu homes for sale is this secluded waterfront Paiko Lagood home. With Kanewai Spring on one side and Paiko Lagoon and wildlife sanctuary on the other, this home claims 700 feet of water frontage--the most on our list. Designed in 1964 by renowned Hawaii archtect Vladimir Ossipoff the home is reminiscent of old Hawaii but upgraded with modern amenities, including an open floor plan and pool.

Property listed by Locations.

*List excludes vacant land for sale.