Imagine escaping to a world of unparalleled luxury and serenity, where Hawaii’s natural beauty unfolds in breathtaking oceanfront vistas and tranquil tropical landscapes. From the iconic Diamond Head views of a Portlock estate to the vast, historic charm of a 293-acre ranch, these eight extraordinary properties—spanning Oahu to Maui—offer rare opportunities for exclusivity. Whether it’s a turnkey condo in a 5-star resort or a sprawling coastal retreat, each embodies the island’s resort lifestyle, promising private sanctuaries with world-class amenities and a deep connection to the Aloha spirit.
Exceptional Portlock Estate | $18,500,000


Listing agents: Keiko Soeda & Carol Ginoza

Listing agents: Keiko Soeda & Carol Ginoza
Set against the breathtaking backdrop of Oahu’s prestigious Portlock shoreline, this exceptional waterfront estate offers a rare slice of paradise. With iconic views of Diamond Head and mesmerizing sunsets, the property captures the essence of island living at its finest. A gated entry welcomes you into a private retreat, where a spacious, flowing floor plan seamlessly connects indoor elegance with outdoor splendor. The tropical landscaped yard, complete with a pool, waterfall, gas BBQ, and a pavilion, creates an idyllic setting for gatherings. Inside, the home boasts a generous primary bath and a striking covered entry, blending comfort with sophistication. Spanning two parcels—a 14,491 sq ft lot with a two-story, five-bedroom, five-and-a-half-bath residence and an adjacent 13,500 sq ft vacant lot—this estate offers endless possibilities. Here, tranquility and luxury converge along one of Oahu’s most coveted beaches.
- Price:
- $18,500,000
- Size:
- 7,021 sq ft
- Contact:
- Keiko Soeda & Carol Ginoza, Zen Properties Incorporated, 808.381.1530 , 808.754.7777
Incomparable 5267Acre Oceanfront | $8,000,000


Regan K. Matsumura

Regan K. Matsumura
Set against the stunning backdrop of the Kohala Coast, this extraordinary rural estate within the exclusive Ranch at Puakea offers a rare chance to embrace the timeless beauty of “old” Hawaii. Spanning two adjoining parcels with zoning approval for dual homes, the property boasts over 1,500 feet of breathtaking ocean frontage. Panoramic views stretch across the Pacific, with glimpses of Maui and vibrant year-round sunsets that transform the sky into a canvas of color. Nestled within a private, intimate community covering 293 acres, the estate promises a serene lifestyle surrounded by natural elegance. Underground utilities, including water, electricity, telephone, and cable, are thoughtfully installed for each parcel, ensuring seamless integration into this idyllic setting. Here, the tranquil rhythm of island life creates a sanctuary for generations to cherish, steeped in Hawaii’s exquisite charm.
Size: 52.67 acres
- Price:
- $8,000,000
- Contact:
- Regan K. Matsumura, Coldwell Banker Island Properties, 808.938.7558
Montage At Kapalua Bay | $4,250,000


Katy Foxwell

Katy Foxwell
Positioned along the serene waterfront of Kapalua Bay, this exquisite residence at the Montage Residences offers a rare glimpse into a luxe island lifestyle. Located in the secluded Building 6, known as the Molokai Wing, Unit 6302 boasts a private elevator and a coveted corner position. Large windows and sliding glass lanai doors frame breathtaking views of Molokai and Oneloa Bay, where seasonal whale watching becomes a cherished morning ritual from the comfort of your lanai. The tranquility of this space blends seamlessly with the elegance of the lush Kapalua Bay resort. Just steps away, explore hiking trails, a bird sanctuary, world-class golf courses, award-winning dining, and rejuvenating spa facilities. With proximity to Kapalua’s iconic Cliff House, tennis courts, and beloved Maui beaches, this furnished retreat embodies the essence of coastal sanctuary and refined living.
- Price:
- $4,250,000
- Size:
- 2,789 sq ft
- Contact:
- Katy Foxwell, Keller Williams Realty Maui-Ka, 808.385.0882
5461 Emi Rd | $2,599,900


Ted Kennedy

Ted Kennedy
Set against the stunning waterfront of Kaua’i’s sunny South Shore, this rare rural estate offers a glimpse into the timeless charm of “old Hawai’i.” Spanning nearly an acre, the property is in the final stages of a CPR process, soon to be divided into two distinct lots. The centerpiece is a beautifully updated 1920s-era home on a sprawling 25,977 sq ft lot, blending vintage island character with modern comforts through a new roof, refreshed floors, and updated windows. With three bedrooms and an open floor plan, it exudes warmth and space. A separate 11,048 sq ft parcel awaits your vision, enveloped by lush tropical greenery and mature avocado and mango trees. Just minutes from Historic Old Kōloa Town, The Shops at Kukui’ula, and the iconic Po’ipū Beach, this serene cul-de-sac retreat offers both privacy and proximity to vibrant island life.
- Price:
- $2,599,900
- Size:
- 1,389 sq ft
- Contact:
- Ted Kennedy, Reside Kauai, LLC, 808.652.9167
928831 Lanikai Drive | $800,000


Nancy Stafford

Nancy Stafford
Rising above the serene landscapes of Kula Kai View Estates, this executive-style home commands a nearly 3-acre parcel on a private dead-end road in a gated mountain community. Revel in breathtaking views of the ocean, Pohue Bay, Queen’s Bath, and South Point from the expansive covered lanai that stretches along much of the residence. Spanning over 3,600 square feet, the interior boasts polished concrete floors with an epoxy finish, granite countertops, a breakfast bar, and a spacious primary suite with lanai access, a jetted bathtub, and a walk-in shower. Modern comforts include split A/C units, motorized blinds, and updated appliances. A massive 1,300-square-foot garage doubles as a workshop with bonus rooms and a half bath—ideal for a home office. With abundant storage, a leased SunRun solar system, and reliable water delivery, this elevated retreat offers both seclusion and convenience.
- Price:
- $800,000
- Size:
- 3,604 sq ft
- Contact:
- Nancy Stafford, ZT Hawaii LLC, 808.937.9255
Ocean Tropical Paradise In Keeau | $349,000


Diana C Prentiss

Diana C Prentiss
Set against the breathtaking eastern shore of Hawaii Island, this waterfront haven in Hawaiian Paradise Park offers an unparalleled connection to the Pacific. Each morning, awaken to the gentle rhythm of waves and the delicate scent of sea air, as Samoan coconut palms sway in the tropical breeze. Unobstructed ocean views stretch endlessly, with sunrises painting the horizon in vibrant hues. Just steps from your door, a scenic cliffside path invites quiet strolls, meditative moments, or spontaneous picnics, all while showcasing dramatic wave scapes. Under the night sky, witness the full moon’s reflection on the water or lose yourself in unrivaled stargazing, free from bright lights or obstructions. This rare coastal retreat promises a lifestyle of serenity, where cool breezes and panoramic vistas become part of your everyday rhythm, blending nature’s beauty with tranquil living.
Size: 1.00 acres
- Price:
- $349,000
- Contact:
- Diana C Prentiss, Ka’u Realty LLC, 808.989.8777
363358 Kuwili Lani Pl | $325,000


Libby Gillis

Libby Gillis
Set against the serene backdrop of the Hamakua Coast, this 1.27-acre waterfront parcel in the exclusive Kuwili Lani community offers a rare fusion of privacy and natural splendor. With only 11 lots in this gated, fully fenced subdivision, residents enjoy an intimate, secure environment tailored for tranquil living. Wake each morning to unobstructed panoramic ocean views that transform the everyday into the extraordinary. The property is primed for development, complete with a geo-tech soil report, topographic survey, solar water heater variance, septic permit, and staked boundaries. Essential infrastructure, including a dedicated water meter, solar-ready capabilities, and fiber optic high-speed internet from Spectrum, ensures modern convenience. Fertile volcanic soil and agricultural tax incentives further enhance its appeal for those envisioning a sustainable lifestyle. This is a sanctuary where breathtaking vistas, security, and thoughtful planning converge seamlessly.
Size: 1.00 acres
- Price:
- $325,000
- Contact:
- Libby Gillis, Fathom Realty LLC, 808.284.5575
Hawaii’s Coveted Location | Contact for pricing


Listing agents: Cedric Choi & Julianna Garris

Listing agents: Cedric Choi & Julianna Garris
Set against the serene backdrop of Honolulu’s most prestigious beach, this rare waterfront estate lot offers an unparalleled opportunity to craft a bespoke retreat. Spanning an impressive 45,271 square feet across two combined parcels, the property boasts 126 linear feet of direct beach frontage, ensuring breathtaking ocean views and immediate access to pristine sands. Located just steps from a notable estate, this expansive lot is a canvas for creating a grand residence in one of Hawaii’s most coveted coastal enclaves. Imagine waking to the sound of gentle waves, enjoying leisurely strolls along the shoreline, or hosting intimate gatherings with the Pacific as your backdrop. With ample space for luxurious design and outdoor living, this property promises a lifestyle defined by tranquility, exclusivity, and the timeless allure of island living.
Size: 1.04 acres
Price: Contact for pricing
- Contact:
- Cedric Choi & Julianna Garris, Hawaii Life Real Est. Brokers, 808.285.2486 , 808.255.7143

















