Imagine waking up to the sound of waves crashing against the shore, surrounded by the unparalleled beauty of Hawaii’s coastline. Nestled in the islands’ most coveted locations, from Diamond Head to Wailea, five extraordinary oceanfront estates redefine luxury living. Priced between $2.65M and $12M, these homes blend bespoke design—think Swarovski chandeliers and custom glass staircases—with seamless indoor-outdoor spaces, private piers, and tropical gardens. Each property is a masterpiece, offering not just a residence, but a sanctuary of prestige, privacy, and connection to nature’s splendor.
Welcome To Diamond House | $12,000,000


Mie Tajima

Mie Tajima
Rising majestically at the base of iconic Diamond Head, this extraordinary estate offers a rare blend of luxury and serenity across over 16,000 square feet of architectural splendor. Soaring ceilings, sweeping staircases, and expansive open spaces bathed in natural Hawaiian light create an atmosphere of timeless elegance. With meticulous details like Swarovski chandeliers and a 3,000+ bottle wine cellar, every corner reflects refined sophistication. Wake to breathtaking ocean views, wander through tropical gardens alive with butterflies, or unwind by the half-moon fountain pool with its cascading waterfall. Perfect for multi-generational living or intimate retreats, this 1.096-acre gated haven ensures privacy. Entertain effortlessly in the gourmet kitchen, host gatherings on the rooftop terrace overlooking Waikiki’s glittering skyline, or savor quiet moments under plumeria trees. Just moments from pristine beaches, Kapiolani Park, and Honolulu’s finest dining and shopping, this mountain retreat redefines elevated living.
- Price:
- $12,000,000
- Size:
- 16,268 sq ft
- Contact:
- Mie Tajima, Real Broker, LLC, 808.224.5339
Unrivaled Oceanfront Maui Luxury | $11,500,000


Ken Smith

Ken Smith
Set against the stunning backdrop of Maui’s coastline, Wailea Point 1404 offers an unparalleled waterfront lifestyle within one of Hawaii’s most prestigious gated communities, nestled between the iconic Wailea Beach and Polo Beach. This reimagined 3-bedroom, 3-bath residence captures the essence of oceanfront living with sweeping views and direct beach access, creating a seamless connection to the Pacific. Inside, a custom glass staircase and bespoke lighting inspired by the starry skies of the Canadian Rockies elevate the space into a true work of art. Thoughtfully curated artwork and designer furnishings enhance the ambiance, blending texture and timeless elegance. Every detail, from the meticulous design to the rare front-row positioning, reflects a commitment to luxury. Ideal for those seeking a serene retreat or a cherished family escape, this home embodies the spirit of island living at its finest.
- Price:
- $11,500,000
- Size:
- 2,430 sq ft
- Contact:
- Ken Smith, Coldwell Banker Island Prop(S), 808.280.4115
A Tropical Modern Masterpiece | $9,369,000


Drew Read

Drew Read
Perched atop an elevated mountain setting, this tropical modern masterpiece offers a rare fusion of luxury and nature with over 120 linear feet of ocean frontage and stunning 180-degree views spanning from Koko Head to Diamond Head. Designed for seamless indoor-outdoor living, the home features a chef’s kitchen equipped with premium appliances like a Wolf gas range, Sub-Zero fridge, and Bosch dishwasher, alongside a butler’s pantry for added convenience. Exquisite details, including custom Sapele Mahogany doors, intricate ceiling designs, and elegant lighting by Fortuny and Fontana Arte, elevate every space. Smart-home technology, air conditioning, and Florim porcelain tile flooring ensure comfort throughout. Outside, a tiled pool, spa, koi pond, and cascading waterfall form a serene oasis, while a private pier with direct ocean access beckons for swimming, snorkeling, or surfing. This is island living redefined.
- Price:
- $9,369,000
- Size:
- 4,302 sq ft
- Contact:
- Drew Read, List Sotheby’s Int’l Realty, 808.782.3636
1009 Kapiolani Blvd Apt 4802 | $3,250,000


Frances Sagun

Frances Sagun
Positioned along the captivating waterfront, the Pacifica Honolulu Penthouse redefines luxury living with its unparalleled design and breathtaking surroundings. This corner unit, boasting 4 bedrooms and 4 bathrooms, offers sweeping vistas of Diamond Head, the Honolulu skyline, and the endless ocean horizon. Inside, elegance unfolds with two primary en-suites, central air conditioning, sleek marble countertops, and rich hardwood floors. A versatile den, in-unit laundry, and generous storage complement the space, while furnishings and appliances ensure immediate occupancy. Residents enjoy exclusive access to a 5th-floor oasis featuring a pool, jacuzzi, gym, and private theaters. With 4 dedicated parking spots, convenience is paramount. Steps away from pristine beaches, upscale shopping, and lively neighborhoods, this penthouse effortlessly blends sophistication with the vibrant pulse of island life, creating a sanctuary where comfort and style harmonize.
- Price:
- $3,250,000
- Size:
- 2,558 sq ft
- Contact:
- Frances Sagun, Royal Realty LLC, 808.368.1964
Panoramic Island Luxury | $2,650,000


Christopher A. Prendergast

Christopher A. Prendergast
Set against the serene backdrop of the ocean, this waterfront executive home in Napali Haweo captivates with sweeping views of the sea and iconic Diamond Head. Designed for luxury and versatility, the residence suits multi-generational living or offers potential for a separate rental unit. The top floor boasts an open-concept design, anchored by a striking marble island and a spacious walk-in pantry, seamlessly connecting to indoor-outdoor entertaining areas. On the middle level, three en suite bedrooms, a family room, and a convenient laundry space await. A lower level with a private entrance features a one-bedroom, one-bath suite, perfect for guests or ohana. Unwind by the private pool or on expansive lanais, where ocean vistas soothe the soul. With 24-hour security, a three-car garage, ample driveway parking, and an energy-efficient 32-panel PV system, this home offers both tranquility and practicality near shopping, dining, and pristine beaches.
- Price:
- $2,650,000
- Size:
- 4,196 sq ft
- Contact:
- Christopher A. Prendergast, 20 Degrees North Real Estate, 808.388.5555




















