Hawaii’s Ultra-Modern Luxury Homes Offer Stylish, Sophisticated, Sustainable Living

Distinctive Dickey rooflines and broad, sloping eves covering gracious lanais have long defined Hawaii’s architectural design. And while these classic elements endure today, sleek modern design, smart home technology, and green living components are trending throughout our island chain.

A handful of the most contemporary luxury estates, situated in some of the most pristine and prestigious locations on Oahu, Maui, Kauai, and Hawaii Island, are showcased below. I’m pleased to share these unique properties with you here, and I look forward to introducing you to many more modern marvels when you begin your search for a home in paradise.

Anekona, Waimea, Hawaii Island

2.62 acres | 2,600 approx. sq. ft. Living | 3BR / 3BA + 2 Half Bath

Designed by San Francisco-based Anderson Anderson Architecture, this contemporary stunner is perched on the desert highlands of north Hawaii Island, just minutes from the charming upcountry town of Waimea.

Sited on a hillside with a south facing aspect, the precise, carefully considered positioning captures sweeping views of majestic mountain peaks, and vast lava fields flowing down to the island shoreline below and the Pacific Ocean beyond. A picturesque stream cascades through desert rocks when rain falls on the cliffs towering above the house to the north.

The house is comprised of a series of identical pavilions aligned in a row beneath a broad, overarching shade roof that serves double-duty as a heavy duty wind deflector and rain collector. The pavilions are enclosed by sliding barn doors on all sides, providing great flexibility in spatial configuration, allowing fine-tuning of shared community space vs. privacy, enclosure vs. expansiveness between pavilions, and between interior and exterior living areas. A row of heavy concrete bunkers create a highly contrasting mass compared to the light and airy pavilions and provide privacy and security for some living and storage functions. The roof wing extends down into the sloping ground, shielding the pavilions from strong trade winds sometimes impacting the area. Nestled among the bunkers and sliding-door pavilions are a series of shaded and open outdoor courtyard spaces

Only the rawest materials were used to construct this unique, environmentally friendly home, including site cast concrete, local hardwoods, pre-fabricated galvanized steel, pre-fabricated weathering sheet steel, lava rock and blue stone gravel, glass, and translucent polycarbonate. All power for the house provided by its rooftop PV array. Energy use, and light and sound intrusion are minimized with all LED lighting, natural ventilation, and cooling.

Founded in 1984, Anderson Anderson Architecture is an internationally respected architecture and urban design firm best known for original, finely crafted modern buildings uniquely developed for individual sites and clients, and for artist collaborations and speculative design innovation.

Haena, North Shore, Kauai

0.54 acres Land | 1,285 sq. ft. Living | 2BR / 1.5BA | Permitted Vacation Rental 

This quintessential, thoroughly modern beach house situated on Kauai’s dramatic north shore was completely renovated in June 2019. Located in Haena with more than a ½ acre of white sand beachfront, Pacific Ocean views are enjoyed from throughout the home. Custom finishes and unique details create a chic but casual vibe. Added benefit: the property has a permitted vacation rental license that transfers with the sale.

Fantastic snorkeling is found just a few hundred feet down the beach, and Haena State Park, Ke’ e Beach and the Kalalau Trail of Napali Coast fame are just minutes away by car with restaurants and shopping found in Hanalei – a short drive in the opposite direction.

The Maui Clifftop House, Kahakuloa, Maui

2.8 Acres | 2,175 sq.ft. Living | 3BR / 3BA + Office 

Featured on the cover of Dwell Magazine and designed by the internationally acclaimed Dekleva Gregoric Architects of Slovenia, Maui’s iconic Clifftop House is a clear example of architecture as living, functional art. Set on 2.8 acres of agricultural land in the island’s Kahakuloa district, the home enjoys a perfect year-round climate and offers ultimate privacy, while just minutes from all amenities, services, and recreational and cultural activities. Its modern design reflects truly organic architecture and clean, healthful environment with all natural elemental surfaces and no paint used anywhere in or on the exterior of the home.

Set high on top of a grassy plateau overlooking dramatic cliffs plunging into the Pacific Ocean below, Clifftop House is perfect for entertaining family and guests and hosting social events. Its design consists of several “houses” under a common roof with each of them possessing a U-shape to bring as much of the spectacular outdoors in – warm sunshine, panoramic views, and refreshing trades.

Since its completion in 2012, the Clifftop house has received massive international attention and garnered several prestigious awards for the architectural firm that was established in 2003.

Beach Road, Diamond Head, Oahu

0.135 acre | 3,996 sqft Living + 198 sq. ft. Lanai + 684 sq. ft. Additional Area | 682 sqft Garage | 4BR / 4BA + 1 Half BA 

Sitting at the base of one of the world’s most recognizable and beloved landmarks – Diamond Head – this premier oceanfront property boasts 122 linear feet of sandy beach frontage. This luxurious, uber-modern three-story beauty was the long-time home of famed fashion designer Geoffrey Beene. The refined, clean lines of the steel and concrete construction reflect Beene’s design aesthetic together with the fine custom details and highest quality materials found throughout the home. Walls of glass provide panoramic ocean, sunrise, and sunset views, even capturing views of the iconic Diamond Head Lighthouse.

An extensive $3 million renovation was completed in 2016 and includes the addition of Smart Home technology, central sound system, ocean-side spa, central A/C, electronic blinds, Photovoltaic System, a multi-car garage and an elevator providing easy access to all 3 levels.

Design details include imported limestone for inside flooring, stainless steel doors, custom glass windows and doors from Fleetwood, and tension cable rails on the lanais, minimizing obstruction of views.

Combining the best of both worlds, this stunning home is blissfully private yet just minutes from Waikiki. Property listed by The CHOI Group with Hawaii Life.

More Information

For information on real estate opportunities on Hawaii Island or the neighboring islands, please contact Jake Chancer, (R), (808) 937-6958 or

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