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$55,000,000
11 Beds ⋅ 11 Baths ⋅ 202520629 MLS ⋅ FS - Fee Simple Tenure
Located on Diamond Head Road, Ho‘oluana Estate is one of Honolulu’s last remaining legacy estate-sized properties, spanning over two acres across two adjacent parcels. Zoned R-7.5 and encompassing nearly 89,120 square feet, the estate features two residences and an open lot, offering sweeping ocean views, beachfront access, and exceptional flexibility for development or preservation. Perfectly positioned between Kahala and Waikiki, this property combines luxury, tranquility, and proximity to world-class surfing, shopping, dining, golf, hiking, and more. Offered as a singular acquisition under TMKs 1-3-1-039-042-0000 and 1-3-1-039-005-0000, Ho‘oluana Estate presents a rare opportunity to establish a landmark estate in one of Honolulu’s most prestigious locations. Property details may not match tax records. Last four digits of the listing TMK do not exist, these are used only for MLS entry purposes.

3735 Diamond Head Road, Honolulu

Listing courtesy of Hawaii Life.

$50,000,000
12 Beds ⋅ 15 Baths ⋅ 202327941 MLS ⋅ FS - Fee Simple Tenure
Unparalleled, the Mele Komo Beachfront Estate located on the pristine shores of Kailua Beach, offers the most discerning connoisseur the ultimate in coastal living. With an impressive 12 beds and 13 baths, this 12,005 square-foot architectural marvel was meticulously designed prioritizing enjoyment with 9 ocean facing bedrooms and 11 private lanais. At 2.2-acres it's the largest residential lot on the Kailua Beachfront. The Primary Hale, boasting 6 beds and 6.5 baths within 5,835 sqft, and the Guest Hale, a companion masterpiece with 6 beds and 6.5 baths spanning 6,170 sqft, offer unparalleled living spaces designed with the perfect combination of luxury comforts and Hawaiian detail. Indulge in resort-style living with a 96,000 gallon pool showcasing a waterfall, slide, jacuzzi, and a private grotto. The 2,000 sqft Pool Cabana with a full kitchen, full bath, spacious loft, and laundry facilities adds an extra touch of convenience and comfort. Mele Komo provides the utmost in privacy and efficiency, featuring 94 photovoltaic panels, privately owned beach access, and stunning views of the famed Mokulua Islands. A unique opportunity to own a true jewel of the Hawaiian coastline.

508 N Kalaheo Avenue, Kailua

Listing courtesy of Compass.

$47,000,000
7 Beds ⋅ 11 Baths ⋅ 726471 MLS ⋅ ['Fee Simple'] Tenure
Kai Lani Cove. Set within Pauoa Beach at Mauna Lani, this oceanfront estate is offered for the first time. Spanning two contiguous lots totaling 2.8 acres with 650 feet of shoreline, the property unfolds laterally across the coast, with multiple structures oriented toward the water rather than positioned behind one another. The compound is composed of ten buildings, including four detached guest homes and a separate two-bedroom bunkhouse with its own living room, kitchen, and terrace overlooking the lawn. The primary suite occupies its own wing, complete with a private pool, spa, dual bathrooms, an office, massage room, and outdoor bathing areas set within lava rock. Living spaces are designed to open fully, removing separation between interior and exterior. Koa cabinetry, coral stone, and exposed timber define the interiors, while the layout prioritizes sightlines, airflow, and direct connection to the landscape. An ocean-facing library and office is positioned above a natural stream system that moves through a network of ponds. Movement across the property unfolds outdoors, between structures, along stone paths, and over water. The land itself remains intact, with anchialine ponds and preserved lava formations integrated into the experience. Pools and spas are set into the terrain, including a central pool with a recessed pavilion, complemented by surrounding lounge seating and a full bar. Outdoor dining areas, a barbecue and pizza oven station, three laundry rooms, a three-car garage, additional motor court parking, and dedicated golf cart and resort vehicles seamlessly support extended stays. At the shoreline, a naturally protected cove provides direct access to calm water for swimming, shaped by reef formations that soften the break. Pauoa Beach is a gated enclave within Mauna Lani, with access to a private beach club, fitness facilities, and resort amenities, offering a level of privacy and access that is not commonly found along this coastline.

68-1023 Pauoa Way, KAMUELA

Listing courtesy of Private Listings by Harold X Clarke.

$45,000,000
8 Beds ⋅ 8 Baths ⋅ 409860 MLS ⋅ Fee Simple Tenure
An exceptionally rare opportunity to acquire two side-by-side oceanfront properties that creates a private coastal compound in one of South Maui’s most coveted enclaves. Positioned approximately 40 feet above a pristine crescent-shaped white sand beach this offering delivers a setting that cannot be duplicated under current coastal regulations. Behind a gated entry, the combined estate offers unmatched scale, privacy, and flexibility ideal as a legacy family retreat, multi-generational compound, or secure oceanfront enclave. Expansive decks from 2 distinct residences project toward the horizon, capturing sweeping panoramic views from Makena to the West Maui Mountains, with year-round sunsets and an ever-changing Pacific backdrop. A gated footpath leads to a secluded stretch of sand known as “Secret Beach,” offering rare, near-private access just steps from your door. Opportunities of this magnitude—two contiguous oceanfront parcels with elevation, privacy, and direct beach access—are extraordinarily limited. Offered together, this is a chance to secure a one-of-one compound in a supply-constrained market where replacement is simply not possible. Minutes from Wailea’s world-class golf, dining, and shopping, yet worlds apart in privacy and setting. Legacy property. Irreplaceable location. Finite opportunity. **Disclosure, some images have been virtually staged**

4640 & 4650 Makena Rd, Kihei

Listing courtesy of Hawaii Life (W).

$43,000,000
5 Beds ⋅ 7 Baths ⋅ 202520630 MLS ⋅ FS - Fee Simple Tenure
Located on Diamond Head Road, Ho‘oluana Estate is one of Honolulu’s last remaining legacy estate-sized properties. Zoned R-7.5 and encompassing nearly 80,000 square feet, the estate features an expansive residences and several open lots, offering sweeping ocean views, private/deeded beachfront access, and exceptional flexibility for development or preservation. Perfectly positioned between Kahala and Waikiki, this property combines luxury, tranquility, and proximity to world-class surfing, shopping, dining, golf, hiking, and more. Neighboring property located at 3735 Diamond Head Road A, is also available for sale, presenting a rare opportunity to establish a landmark estate in one of Honolulu’s most prestigious locations. Property details may not match tax records.

3735- Diamond Head Road, Honolulu

Listing courtesy of Hawaii Life.

$37,500,000
5 Beds ⋅ 9 Baths ⋅ 202528159 MLS ⋅ FS - Fee Simple Tenure
The Hemmeter Estate is a rare, oceanfront estate located at the end of Kaikoo Place on Black Point. Featuring an extraordinary 339.45 linear feet of ocean frontage, this property offers one of the most expansive coastal settings in Hawaii, with exceptional frontage in the heart of Kaikoo. Blending Hawaiian natural elements with European Renaissance–inspired design, the residence showcases exceptional craftsmanship throughout. Set on 35,870 sq ft of land, the estate offers approximately 21,266 sq ft of interior living, complemented by extensive covered and open lanais ideal for entertaining. Highlights include cast-bronze entry doors, coffered Venetian-inspired ceilings, Italian perlato marble staircases and flooring, carved and finished on-site, a two-story oceanfront living room, and refined Art Deco bronze detailing. Amenities include a private theater, library, entertaining lounge, and grotto pool. The expansive primary suite spans nearly 5,000 sq ft and features dual dressing rooms, a fitness area, and sweeping coastline views. The Hemmeter Estate is an irreplaceable oceanfront estate distinguished by scale, privacy, and architectural significance.

4324 Kaikoo Place, Honolulu

Listing courtesy of Compass.

$35,000,000
2 Beds ⋅ 2 Baths ⋅ 408193 MLS ⋅ Fee Simple Tenure
Hana Ranch is the largest offering on Maui and one of the few remaining private holdings of this size in Hawai‘i. Established as a working cattle ranch in 1944, it remains an iconic agricultural land holding encompassing approximately 3,006 fee simple acres. The sale includes 26 separate parcels, allowing for the creation of a secluded estate with multiple homesites. The ranch features ocean and mountain views and is managed by a dedicated paniolo using sustainable, diversified agriculture and silviculture practices. Stewarded over its history by only a handful of owners, the current owner developed a land use plan based on regenerative agriculture and environmental stewardship. This includes rotational grazing, orchards of tropical fruit and ulu (breadfruit), and the restoration of forests and watersheds. A variety of vegetable crops have been grown and marketed on the land over the years, with potential for large-scale production. Included in the sale are a two-bedroom farm house with direct ocean views, equestrian facilities (including a rodeo arena), ranch and farm buildings and equipment, multiple wells and storage tanks, and fencing and gates for rotational grazing. Abundant water resources are managed by two operating water companies. Ranch roads and hiking or equestrian trails traverse rolling pastures and upland forests. Hana, Maui, located on the eastern slope of Haleakala, is a verdant coast that was one of the first areas settled by voyaging Polynesians and remains a thriving community proud of its heritage. Access the ranch via the historic Hana Highway, fly into Hana airport (10 minutes away), or utilize the helicopter landing site on the ranch. Rich in history and future possibilities, Hana Ranch presents the opportunity to create a legacy for generations to come.

5670 Hana Hwy, Hana

Listing courtesy of Hawaii Life (PR).

$34,000,000
6 Beds ⋅ 7 Baths ⋅ 726361 MLS ⋅ ['Fee Simple'] Tenure
Property owners are extended the opportunity to apply to the Kukio Golf & Beach Club: an oceanfront private club with world class amenities including Tom Fazio designed 18-hole Championship Golf Course and 10-hole short course, two clubhouses with private dining, sports complex, ocean pursuits center, and a comprehensive indoor and outdoor spa. Gatehouse entry with 24-hour manned security.

72-3177 Punaloa Pl, KAILUA KONA

Listing courtesy of Kukio Properties.

$33,000,000
5 Beds ⋅ 6 Baths ⋅ 731430 MLS ⋅ ['Fee Simple'] Tenure
Brand-new luxury residence on a spacious 1.02-acre homesite within the prestigious gated community of Kaupulehu. Offered fully furnished and move-in ready, this exceptional estate features 6,350 sq. ft. of interior living space and 1,635 sq. ft. of lanai space, with five ensuite bedrooms, five full baths, and one half bath, thoughtfully designed for seamless indoor-outdoor island living. Ownership includes privileged access to the Kaupulehu Beach Club, featuring a two-tiered swimming pool, hot tub, fitness center, expansive event lawn, bar and dining pavilion, and a pathway to a secluded black-sand beach, offering an unparalleled resort-style experience. Signature Details: • 6,350 sq. ft. of refined interior living space and 1,635 sq. ft. of resort-style lanai space • Five ensuite bedrooms, five full baths, and one half bath • Fully furnished and move-in ready for effortless Kaupulehu living • Designer kitchen featuring premium appliances • Expansive great room with pocketing doors that open to outdoor entertaining areas • Elegant primary suite offering a serene, retreat-style ambiance • Welcoming guest suites thoughtfully designed for comfort and privacy • Luxury craftsmanship, bespoke finishes, and sophisticated island-inspired design throughout • 964 sq. ft. three-car garage with ample room for vehicles, golf carts, and storage • Situated on a private 1.02-acre homesite offering exceptional privacy and tranquility • 24-hour access-controlled community • Panoramic ocean and mountain vistas overlooking a 214-acre cultural preserve rich in Hawaiian history More than a home, this is a statement of lifestyle, privacy, and elevated Hawaiian living. A newly built sanctuary where luxury meets the landscape, framed by breathtaking ocean and mountain vistas that create an extraordinary backdrop for everyday life. Additional professional photography is forthcoming.

72-1174 Kekahawaiole Dr, KAILUA KONA

Listing courtesy of Corcoran Pacific Properties.

$32,500,000
6 Beds ⋅ 8 Baths ⋅ 728630 MLS ⋅ ['Fee Simple'] Tenure ⋅ Kohola Point BLDG.
Set on 6.87 acres above Anini Reef on Kaua‘i’s North Shore, this bluff-top estate is defined by its rim lot position and scale. The site allows for a distribution of structures and separation not achievable on smaller parcels along this stretch of coastline. Contemporary architecture is set low against the land, oriented to capture light, trade winds, and views across ocean, reef, and mountains. From sunrise over Kīlauea Lighthouse and the shores of Secret Beach, to Kalihiwai Bay at sunset, the view shifts throughout the day. The reef below moves between turquoise and deep blue as light and clouds move across it. Dolphins are visible from the bluff, and in season, humpback whales often pass by with their calves. The residence is composed as a connected series of pavilions, linked by covered walkways and lanais that move through the landscape as a single home. Floor-to-ceiling glass walls and sliding doors open each space to the outdoors, while the surrounding grounds reinforce privacy and separation. The primary suite is set apart. Three guest suites anchor the main residence. Detached guest residence and gym are private and self-contained, each with independent entry and orientation. Reef and ocean views extend from nearly every room. Set within Anini Vista at the end of a gated cul-de-sac with no through traffic. Princeville is minutes away. Hanalei within easy reach. Property Highlights: 18,210 sq ft under roof 10,320 sq ft of interior living space Primary suite with its own structure Three additional guest suites Detached guest residence Gym Media room Office Lagoon-style saltwater pool with grotto, waterfalls, bridge, and spa Air conditioning throughout

4200 Anini Vista Dr Unit D, KILAUEA

Listing courtesy of Hawaii Life.

$32,500,000
3 Beds ⋅ 3 Baths ⋅ 728649 MLS ⋅ ['Fee Simple'] Tenure
A visionary hideaway originally crafted in Indonesia and painstakingly reassembled on the pristine shores of the Big Island offers a once-in-a-generation opportunity to own an architectural masterpiece. Where jagged lava fields meet the endless azure of the Pacific Ocean sits the crown jewel of the Kohala Coast. Far more than a residence, this compound is a testament to extraordinary personal vision and global craftsmanship. This is a magnificent Balinese estate transported across the sea to rest seamlessly upon Hawaiian shores. Kiholo Bay is a marvel of untouched nature, and this property respects that raw beauty. Designed in the traditional Balinese style, the estate is organized as a rhythmic series of independent pavilions. These structures are thoughtfully arranged in a compound layout woven together by a network of open-air decks and sheltered walkways. Originally built in Bali by 280 master craftsmen using Indonesian ironwood and teak, the structure was dismantled and shipped, then reassembled in Hawaii using traditional wooden pegs. Its most striking feature is a massive roof of over one million wooden shingles meticulously laid to resemble dragon skin. The interior serves as a living museum blending Southeast Asian history with the Hawaiian environment. Living spaces are adorned with intricate Indonesian carvings while sliding doors vanish to invite the Pacific breeze. The kitchen sits in its own circular pavilion, designed to promote natural airflow and effortless outdoor dining. The retreat includes an expansive direct ocean primary pavilion. From this vantage point, sliding walls reveal a breathtaking panorama where the deep blues of the Pacific transition into the rising silhouettes of the Kohala Mountains. Completely self-sustaining with its own water and solar systems, the estate is a resilient cultural masterpiece that harmonizes the spirit of Bali with the majesty of the Big Island.

71-1890 Queen Kaahumanu Highway, KAILUA KONA

Listing courtesy of COMPASS.

$31,900,000
5 Beds ⋅ 8 Baths ⋅ 727861 MLS ⋅ ['Fee Simple'] Tenure
Gracefully positioned in one of the most coveted communities on the Kohala Coast of the Big lsland of Hawaii, this oceanfront 7,844 -square-foot residence on 1.38 acres at the Cape at Mauna Lani offers five bedrooms, seven and a half baths, a spacious media room and a private office, designed by renowned Lucky Bennett to capture sweeping ocean, fairway, mountain and sunset views. A formal entry with waterfalls and ponds creates a dramatic reveal of the great room and the Pacific beyond. Inside, soaring ceilings, Brazilian cherry and flamed granite floors and architectural symmetry define the expansive living space. A striking fireplace wall framed by custom wood paneling and curated niches anchors the room, while disappearing pocket doors open completely to the oceanfront lanai, infinity-edge pools and spa that appear to merge seamlessly with the ocean. The warm chef inspired kitchen features rich, custom cabinetry, generous workspace and a seamless connection to the dining area, outdoor gathering area and ocean beyond. The primary suite is situated on the south corner in a private wing with fairway and ocean frontage and his and her spa-inspired baths. Guest bedroom suites are thoughtfully separated for privacy. The dedicated media room, overlooking the ponds and waterfalls provides an immersive retreat for film and entertainment, while the private office offers a quiet, light-filled workspace with inspiring coastal vistas. Manicured lawns, charming sculptures, lava rock walls, and curated tropical landscaping frame the infinity pool and spa. The property has rare dual frontage—dramatic ocean cliffs and emerald fairways on the other. This is a legacy residence, an architectural statement, dramatic and timeless.

68-1339 Kaniku Dr, KAMUELA

Listing courtesy of Corcoran Pacific Properties.

$31,000,000
9 Beds ⋅ 10 Baths ⋅ 202600075 MLS ⋅ FS - Fee Simple Tenure
The Mokulua Estate is a breathtaking oceanfront sanctuary set within the prestigious Lanikai neighborhood. This exceptional property offers unobstructed views of the Mokulua Islands from nearly every vantage point. With over 150 linear feet of ocean frontage and a private gated entrance, the estate provides an ideal blend of seclusion, security, and harmony with its natural surroundings. Encompassing more than 10,000 square feet of refined indoor/outdoor living space, this state-of-the-art residence, designed by award winning architect Jim Jennings showcases dramatic ocean and mountain vistas throughout. A guest house and caretaker’s quarters ensure ample accommodation for family and guests. Direct ocean access from the backyard invites an active island lifestyle, from swimming and snorkeling to kayaking, surfing, fishing, or simply relaxing by the pool in your own tropical paradise. This is a rare, Once-In-A-Lifetime offering you won’t want to miss!!

1240 Mokulua Drive, Kailua

Listing courtesy of List Sotheby's Int'l Realty.

$30,000,000
4 Beds ⋅ 4 Baths ⋅ 715459 MLS ⋅ ['Fee Simple'] Tenure
Behold! The most dramatic oceanfront setting and vista situated along the coastline in all of Poipu. Hale Moku (Ship House in Hawaiian) was originally built in 1936 and remodeled over the years, cleverly designed and constructed on a solid lava rock outcropping safely above the waterfront with semi-circular decks off the living room and master (primary) bedroom above, facing the ocean - all which give the strong sense of being on the bow of a ship piercing and advancing through the incoming rolling waves below. The subject property encompasses three contiguous parcels adding up to approximately 25,586 sf. The main living area consists of 4 bedrooms, 3.5 baths, and a separate attached fully self-contained caretakers' quarters. This property is located on the southwestern most point of the US offering unobstructed views of 50+ square miles of the South Pacific horizon with panoramic views from Makahuena, the Poipu coastline, Spouting Horn, and the Island of Niihau in the distance. As you relax and take in the views, you actually experience a feeling of totally immersing yourself within an invaluable living painting that is forever changing as the days pass with breathtaking sunrises and sunsets, incomparable to anywhere else on the planet. One also experiences watching innumerable turtles frolicking in the surf and gathering in Turtle Cove below and schools of Spinner dolphins cruising by as they meander down the coast. You may also enjoy watching Humpback Whales breaching nearby between November and April as they migrate from Alaska to the warm Hawaiian waters during the wintertime to give birth to their offspring. Poipu and Shipwrecks beaches are only a leisurely 10-minute walk away with several excellent restaurants within walking distance, as well. Your biggest challenge owning or having the privilege in staying at Hale Moku is ever leaving, once you are there... Listing includes two additional parcels, TMK 4-2-8-20-060 (Lot A) and TMK 4-2-5-20-061 (Lot C).

1711 Pee Rd, KOLOA

Listing courtesy of Coldwell Banker Island Properties - Kauai.

$29,900,000
5 Beds ⋅ 6 Baths ⋅ 407766 MLS ⋅ Fee Simple Tenure
Perched on one of Makena’s most coveted cliffside locations, this contemporary direct-oceanfront estate is perfectly situated along an intimate cove, offering breathtaking, unobstructed Pacific views from nearly every room. Set on over 22,190 sq. ft. of land, this two-story, five-bedroom, five-and-a-half–bath residence is a masterpiece of luxury and Hawaii’s signature indoor–outdoor living. Designed by world-renowned architect Guy Dreier, the home is a livable work of art, featuring soaring ceilings, dramatic architectural lines, and an innovative floor plan. Step through the entryway into an entertainer’s paradise. The expansive great room flows effortlessly through large pocket doors to the oceanfront deck, where a stunning infinity-edge pool appears to spill into the sea—ideal for sunset gatherings or peaceful mornings with coffee in hand. Multiple living and dining areas, along with a dedicated service area, create an unparalleled setting for both intimate dinners and large-scale celebrations. The exquisite primary suite and three guest suites each offer private ocean-view lanais, providing serene retreats with panoramic vistas. A beautifully appointed attached Ohana unit adds exceptional flexibility for guests, extended family, or a caretaker. Move-in ready and designed for effortless hospitality, this is more than a home—it’s a true Makena masterpiece blending modern coastal luxury with the timeless beauty of Maui’s south shore.

5050 Makena Rd, Kihei

Listing courtesy of Discovery Makena Realty LLC.

$26,500,000
6 Beds ⋅ 6 Baths ⋅ 409734 MLS ⋅ Fee Simple Tenure
THE ULTIMATE MAUI DREAM . .The most sophisticated are no longer asking where to live . .They are asking, “Where can we breathe?” Welcome to The Makena Generational Oceanside Retreat offering resort-style living with smart-home technology, unobstructed ocean & sunset views, Haleakala sunrise views situated on a professionally landscaped one-acre gated and walled tropical estate.The fully operational compound is ready for occupancy offering a vast combination of energy efficiency, self-sufficiency and refined comfort featuring the largest residential Tesla Solar Roof in the US installed in 2024. A unique opportunity to own a private Maui sanctuary of this stature where luxury, wellness and sustainability coexist in harmony. The indoor-outdoor lifestyle is designed for multigenerational living, executive retreats and legacy ownership. In a world moving faster than ever, it is intentionally crafted for life to slow down. Extensively upgraded under the current owner with substantial infrastructure, aesthetic and technology enhancements, the property is now offered well below current replacement cost. The Makena community remains one of Maui’s most coveted luxury destinations. The current property manager creates effortless luxury living with lock-and-leave convenience. The luxurious amenities are endless. The privately separated interior living areas offer exceptional craftsmanship, premium wood finishes, floor-to-ceiling bifold glass doors, elevator, gourmet kitchen, exercise area, massage room, sauna, and steam shower. The dramatic custom water features include a puka lava entry waterfall with pond and interior floor-to-ceiling water feature at the base of the floating staircase. The additional luxury oceanside pool home with its oversized heated pool includes its own gourmet kitchen, Italian brick pizza oven and rear projection entertainment system. Combined with many additional features, the estate offers a total of 8b-8b comfortably accommodating up to 16 guests. Parking is a breeze with a 4+car garage and generous additional parking areas.

7505 Makena Rd, Kihei

Listing courtesy of Compass-W.

$26,500,000
6 Beds ⋅ 5 Baths ⋅ 728631 MLS ⋅ ['Fee Simple'] Tenure ⋅ Silver Falls Estates BLDG.
Silverfarms Ranch is a North Shore sanctuary where water, mountains, and open pasture converge across more than 237 acres of remarkable Kaua‘i landscape. Set beneath the towering ridges of Mount Namahana, the property offers streams, waterfalls, swimming holes, and sweeping views that capture the essence of Kaua‘i’s natural beauty. With two existing residences, equestrian facilities, and future building potential, the ranch presents a rare opportunity to create a multi-generational estate just minutes from the charm of Kilauea and the world-class beaches of Hanalei and Princeville. Silverfarms ranch is comprised of three separate parcels totaling more than 237 acres. The largest parcel spans 137.69 acres and serves as the operational heart of the ranch. It includes two residences along with a variety of agricultural and equestrian facilities, including multiple horse stable areas, an office, and a covered riding arena making it ideally suited for equestrian operations or an expansive private ranch estate. The residences include: A 4-bedroom, 3.5-bathroom main residence spanning 3,509 sq ft A 2-bedroom, 1-bathroom residence totaling 1,080 sq ft The 92.18-acre parcel offers beautiful, undeveloped Kaua‘i land with a network of riding trails and a mix of open pasture and forested areas. Zoning allows for the development of a single-family residence. The property also enjoys separate private access via its own road and a custom bridge, offering both convenience and privacy. The smallest parcel at 7.92 acres also allows for the development of a dwelling. It currently serves as a grazing and tending area for horses associated with the ranch. Silverfarms Ranch invites you to imagine a life where adventure, exploration, and tranquility meet…

2818 Kamookoa Rd Unit 1, KILAUEA

Listing courtesy of Hawaii Life.

$26,500,000
5 Beds ⋅ 8 Baths ⋅ 202603726 MLS ⋅ FS - Fee Simple Tenure
Experience unmatched sophistication in this one-of-a-kind, award-winning home by Nicholson Companies, now available at an exceptional value—priced below the 2024 appraisal! This modern masterpiece, nestled in the prestigious Cove Area of Diamond Head, offers over 7,465 square feet of living space that seamlessly blends cutting-edge design with island inspiration. From the expansive living areas that capture breathtaking views to the advanced whole-house automation and security systems, this home is a true technological marvel. The chef's kitchen, featuring professional-grade appliances and a spacious butler’s pantry, is a culinary dream. Every corner reveals something extraordinary, from the exquisite interior finishes to the stunning outdoor oasis. This beachfront home represents the pinnacle of island living, now available at an exceptional price that underscores its unmatched quality and prestige. Seize the opportunity to own this extraordinary residence and make it your own private paradise.

213 Kaalawai Place, Honolulu

Listing courtesy of Coldwell Banker Realty.

$24,900,000
7 Beds ⋅ 9 Baths ⋅ 725915 MLS ⋅ ['Fee Simple'] Tenure
Kilohana sits on a 1.4-acre front-row site at the end of a private drive within the 49 Black Sand Beach neighborhood at Mauna Lani. Honoka’ope Bay, with its black sand beach and private community beach club, is less than a 90 second walk from the home. Overlooking the 7th hole of Mauna Lani’s south course, the property has over 275 feet of frontage on views of the ocean, waves crashing on the shoreline, Maui, and sunsets from four of the bedrooms and all living areas. The improvements are laid out as a small village retreat, with mature landscaping and stone pathways leading to the many private locations on the property, and include a solar field and putting green with a 45-yard pitch to the green. On the south side of the property, adjacent to the golf course buffer, sits the 1,750 square foot ocean view primary suite with a spacious two-station office, two full bathrooms, a large shower garden, and full laundry facilities. On the north side of the property are two detached 3 bedroom, 3 bath, 1,300 square foot guest hale, each with its own laundry facility and between the two hale, are an additional four outdoor shower gardens. The numerous pocket doors throughout beckon you to a 1,656 square foot lanai including a 600 square foot grand covered lanai with wet bar, dining area, sunken barbecue, with smoker and cooktop; almost 8,000 sf of indoor/outdoor living at its best! Large 3 car garage with private entrance, as well. The home was designed by Lucky Bennett and built by Clever Construction to exacting standards, which include mahogany pocket doors, windows, floors and trim, vaulted ceilings, a variety of custom stone and tile used throughout and a lengthy list of designer furnishings and art included in the sale. Meticulously designed and cared for by an owner who is in the real estate development business!

68-1115 Honokaope Pl Unit 1, KAMUELA

Listing courtesy of Hawaii Life.

$24,900,000
10 Beds ⋅ 9 Baths ⋅ 202525519 MLS ⋅ FS - Fee Simple Tenure
Live among Hawaii's natural wonders & unsurpassed beauty at this extraordinary Pahonu Beach estate. Spanning nearly 1 acre, this oceanfront property includes 152 linear feet along the Pacific Ocean. Nestled in a private, gated location, the 2 lot compound offers over 8600 sq ft of living area in its main house, guest house, cottage, and studio. Expansive lawns provide mesmerizing views across the ocean to Manama (Rabbit) Island and stunning vistas of the Koolau Mountains. The main house completed in 2022, sets a new standard of quality craftsmanship. Exceptional design, flawlessly executed using premium materials, creates a luxurious, beautiful, and comfortable home. Floor to ceiling sliding glass doors span the oceanfront side, providing spectacular views of the lush landscaping and ocean. The gourmet kitchen includes top of the line appliances, custom walnut cabinetry, and a disappearing pantry consistent with its sleek, modern design. Next door includes a 3BR oceanfront guest house, 2BR cottage and studio. This irreplaceable compound offers its next owner an opportunity to enjoy a spectacular lifestyle with family and friends in a magnificent oceanfront setting.

41-471 Kalanianaole Highway, Waimanalo

Listing courtesy of Caron B Realty.

$24,500,000
4 Beds ⋅ 6 Baths ⋅ 408751 MLS ⋅ Fee Simple Tenure
One-of-a-Kind Keawakapu Beachfront Estate in one of Maui’s most coveted oceanfront settings, offering an extraordinary blend of irreplaceable beach proximity, modern structural integrity, and timeless refined island design. The residence was completely rebuilt from the foundation up, completed in 2013—retaining only the original pool and foundation to preserve its rare, grandfathered beachfront setback. The result is a fully reimagined wood-framed home enhanced with structural steel beams, allowing for expansive open spans and a modern layout. The estate includes a spacious main residence, separate guest home, and three-car garage, creating a private compound ideal for multigenerational living or luxury hosting. Designed for unforgettable gatherings, multiple indoor and outdoor living spaces flow effortlessly to a spectacular resort-style pool with slide, hot tub, waterfalls, and dramatic rock grotto. A distinctive basement level serves as the ultimate retreat, featuring a game room with custom Koa wood bar, in-home gym, craft room, and additional guest suite with full bath. Lush tropical landscaping, sauna, and multiple outdoor showers enhance the resort-caliber experience. The chef’s kitchen and dining area showcases Sepalle wood detailing and striking Labradorite granite countertops, blending warmth with sophistication. The primary suite is a sanctuary, complete with a spa-inspired bath featuring a floating tub, private sundeck, and panoramic Haleakala views. Throughout the property, incredible details and textures create a custom, curated feel. Meticulously rebuilt in 2013 to combine modern structural capability with an irreplaceable oceanfront location, this legacy beachfront estate represents a rare and irreplaceable offering on Maui.

3060 S Kihei Rd, Kihei

Listing courtesy of Coldwell Banker Island Prop(S).

$24,500,000
5 Beds ⋅ 6 Baths ⋅ 408059 MLS ⋅ Fee Simple Tenure
Experience the pinnacle of oceanfront luxury in this stunning, 5 bedroom, 5 bath, plus 2 half bath, 7,244 sq. ft. home estate. This over a half-acre property is located within the ideal stretch of Keawakapu Beach, offering unparalleled access to Maui’s most coveted shoreline. This architectural triumph blends contemporary elegance and convenience with the island’s natural beauty, creating a private sanctuary of sophistication and rare serenity. This estate features 5 spacious en-suite bedrooms, multiple areas for relaxed socializing, and a seamless indoor-outdoor flow that embraces the home’s stunning pool courtyard and oceanfront experience. Every room gifts an extraordinary vantage point of paradise – between sweeping ocean views in three master suites or tranquil poolside perspectives from the guest suites. At the heart of the home, the expansive pool and courtyard form a striking focal point, linking the media room, main entry, and living areas in perfect harmony. A private poolside retreat ensures both security and discretion, ideal for intimate gatherings or large-scale entertaining. Landscaped gardens with numerous palm trees and second-level sundecks off the guest suites provide elevated spaces to soak in a front seat view of unforgettable sunsets. A spacious oceanfront lawn offers ultra-privacy, featuring a fire pit that creates an inviting ambiance, shielded from public view and accessible only through a discreet, gated beach entrance. Whether you seek a primary residence, a lavish vacation home, or an island retreat, this estate is designed for those who desire premium beachfront living with an ultimate feel of privacy. A rare opportunity to own the most memorable oceanfront lifestyle in Maui.

3254 S Kihei Rd, Kihei

Listing courtesy of Hawaii Life (W).

$23,000,000
8 Beds ⋅ 12 Baths ⋅ 731346 MLS ⋅ ['Fee Simple'] Tenure
A single oceanfront compound fronting Tunnels Beach, in Hāʻena on Kauaʻi’s north shore, joins two individually deeded parcels offered together as one. Nearly three acres run the full depth from Kūhiō Highway to the beach, with approximately 250 feet of beachfront. The principal residence stands at the water, circular in plan, its broad lānai and walls of glass open to the Pacific. Set back among the palms, the second is a wood plantation home beneath a terracotta-colored metal roof, offering four additional bedrooms with mountain, garden, and filtered ocean views. Open lawn runs unbroken to the beach, with mature gardens, a screened pavilion, and a tennis court. The oceanfront residence is fully renovated and in exceptional condition; both homes are fully air conditioned and carry solar and Tesla Powerwall battery storage. Together, the compound offers approximately 9,575 square feet and eight bedrooms in one of Hāʻena’s most significant oceanfront holdings. The Napali Coast, with its dramatic terrain and renowned hiking trails, is just a short drive to the “end of the road.” Hanalei’s charming town and crescent bay are approximately 15 minutes away, offering world-class dining and surf, while Princeville’s golf courses, shopping, and resort amenities are just beyond.

5-7534 Kuhio Hwy, HANALEI

Listing courtesy of Hawaii Life.

$23,000,000
3 Beds ⋅ 5 Baths ⋅ 724076 MLS ⋅ ['Fee Simple'] Tenure
LUXURY PROPERTY AUCTION: 13–25 August. Accepting starting bids through 12 August Earn an incentive by 12 August. Wahi Lani, meaning heavenly place in Hawaiian, captures the spirit of Hanalei Bay just steps from its white sand shoreline. Completed in 2022 by acclaimed architecture firm Walker Warner, this newly built residence pairs sleek, modern design with an unmistakable surfer's ease and direct access to some of Kauai's most celebrated waves. A central courtyard anchored by a Heath ceramic infinity pool draws the outdoors in, framed by dramatic Shou Sugi Ban walls, a traditional Japanese charring technique lending rich, textured depth throughout. Honey-toned cedar and oak siding complement a warm ipe wood deck, while an integrated indoor pizza oven brings culinary flair to the open-air lanai. Surfboard storage, outdoor showers, and a foot-washing station suit life spent between sand and sea, while wide gates foster easy connection with the neighborhood. Moments from Hanalei Town and close to Princeville, Wahi Lani offers privacy, style, and coastal immersion on Kauai's storied North Shore.

5515 Weke Rd, HANALEI

Listing courtesy of Hawaii Life.

$23,000,000
4 Beds ⋅ 5 Baths ⋅ 402062 MLS ⋅ Fee Simple Tenure
Nestled along the prestigious Makena coastline, 7595 Makena Road represents the pinnacle of contemporary Hawaiian luxury living. This extraordinary residence stands as a masterpiece where architectural innovation meets paradise. Perched on an expansive and private one-acre lot, this four-bedroom haven commands breathtaking views of the mesmerizing Ahihi Bay, where emerald and turquoise waters dance in eternal harmony. Each morning brings nature's theater to your doorstep, with the gentle lapping of waves providing the perfect soundtrack to your day. The dwelling is comprised of a total of 6643sf: 4778sf of living space, 995sf of covered lanai space to enhance the indoor/outdoor living, and an oversize, three-car garage of 870sf. The home's thoughtful design seamlessly integrates indoor and outdoor living spaces, featuring: - Four luxurious en-suite bedrooms, each offering a private sanctuary - Open-concept baths with spacious showers and captivating ocean views - State-of-the-art smart home technology throughout - Private elevator ensuring effortless accessibility - Custom finishes that reflect both modern luxury and island charm As one of Makena's newest luxury estates, this residence offers more than just a home – it's an invitation to experience Maui's most coveted lifestyle. The property's privileged location provides the perfect vantage point for witnessing the island's legendary sunsets and seasonal whale watching. Built in 2022, this contemporary masterpiece represents the perfect blend of modern amenities and timeless island elegance. Every detail has been carefully curated to create an environment where luxury isn't just a feature – it's a way of life. This rare offering stands as a testament to sophisticated island living, where every detail has been thoughtfully designed to create an unparalleled living experience in one of Maui's most sought-after locations. Don't let this unparalleled Makena estate slip away – seize the opportunity to be the first owner of this exceptional estate.

7595 Makena Rd, Kihei

Listing courtesy of Compass-W.

$22,500,000
7 Beds ⋅ 6 Baths ⋅ 731606 MLS ⋅ ['Fee Simple'] Tenure
Five standalone beach cottages on three legal parcels, totaling roughly 60,000 square feet and more than 200 linear feet of direct golden-sand frontage on Kauaʻi’s North Shore. Each cottage is a complete house, single-story and at grade, with its own deck, kitchen, living room, and private entrance. Three are one-bedroom units of approximately 700 square feet. Two are two-bedroom villas, the larger of which sits on its own adjacent parcel at 4414 Oneone Road with two full baths, a 400-square-foot covered lanai, and dedicated off-street parking. All five were fully renovated in 2025, with new systems, kitchens, baths, and finishes throughout, plus three new aerobic septic systems. Additionally, all five have transient vacation rental licenses allowing for short term rental use. The compound fronts Baby Beach, where the reef keeps the water calm and swimmable through most of the year. More than fifty mature coconut palms shade the open lawn connecting all five cottages. A detached laundry building includes two washers, two dryers, a commercial ice machine, and gear storage. Finally, the third adjacent parcel is vacant and can be improved with an additional home to complete your vision. The property can be operated as a hosted vacation rental or held entirely private. Hanalei is a short drive east. The road ends west of the property at the Nā Pali Coast.

4400 Oneone Rd, HANALEI

Listing courtesy of Hawaii Life.

$22,000,000
6 Beds ⋅ 10 Baths ⋅ 202606611 MLS ⋅ FS - Fee Simple Tenure
When a residence transcends architecture, it becomes a work of art. Set across 1.81 acres in the misted beauty of Nuuanu, LIHIWAI is one of Hawaii’s most iconic historic estates, a rare convergence of land, design, and legacy in a truly cinematic setting. Originally built between 1927 and 1929 for Territorial Governor George R. Carter and designed by Bertram Grosvenor Goodhue, the home has been completely restored and is offered following a meticulous renovation by Welch & Weeks, a museum-quality restoration for modern living. Gracious volumes, natural light, and a refined material palette, including ohia hardwood, old-growth redwood, plaster, bronze windows, and limestone, create spaces that feel both expansive yet intimate. The four-bedroom, seven-bathroom main residence is complemented by two guest homes. The grounds unfold as a private sanctuary with a natural auwai, flowing stream, dramatic waterfall, and heated saltwater pool and spa. Set within Nuuanu Valley, this is a composition of historic pedigree, quiet luxury, and natural beauty. A legacy estate, now coming to market.

51 Kepola Place, Honolulu

Listing courtesy of Hawaii Life.

$21,000,000
4 Beds ⋅ 6 Baths ⋅ 731952 MLS ⋅ ['Fee Simple'] Tenure
Experience the pinnacle of luxury living at 2838 Kapoli St in the exclusive Kealia Kai subdivision. This brand-new, nearly oceanfront estate showcases unmatched craftsmanship, custom designer furnishings, and meticulous attention to every detail. The main residence offers approx 6,000 sqft of interior living space complemented by over 2,400 sqft of covered lanais designed for seamless indoor-outdoor living. Floor-to-ceiling pocket glass doors frame unobstructed panoramic ocean views, with the sand of Donkey Beach in sight, along with breathtaking vistas of Wai‘ale‘ale and Makaleha mountain ranges. Enjoy beach access, endless views, and complete privacy on this nearly 7-acre estate. Inside, an expansive kitchen features Wolf appliances, a La Cornue French stove, a butler’s pantry, and an oversized island, ideal for entertaining and culinary pursuits. The primary suite is a private retreat, highlighted by an Alaskan king bed, luxurious finishes, and direct access to an ocean-view lanai. Each bedroom includes its own ensuite bath and private lanai, creating individual sanctuaries for family and guests. Custom designer furnishings enhance every room, while invisible speakers, integrated audio-visual systems, and hidden gutters elevate both form and function. Additional features include a 1-bedroom, 1-bathroom guest house (approx. 1,100 sqft with 650 sqft lanai), a 650 sqft gym, and two garages, each exceeding 550 sqft. Outdoor living is defined by a 25’x50’ pool and a 10’x10’ spa, set against the backdrop of Kaua‘i’s dramatic coastline and mountain ranges. From stamped lava rock impressions on the driveway to cutting-edge smart home integration, no detail has been overlooked. This is a rare opportunity to own one of Kaua‘i’s finest new builds. Ideally located walking distance to the coastal trail, beaches, shopping, restaurants and more! Pool construction and final landscaping is underway. Virtual renditions included in photos.

2838 Kapoli St, KEALIA

Listing courtesy of COMPASS.

$21,000,000
6 Beds ⋅ 7 Baths ⋅ 730631 MLS ⋅ ['Fee Simple'] Tenure
Perched majestically atop 1.62 acres of prime ocean-view land within The Bluffs exclusive gated community at Mauna Kea Resort. Mauna Kea Resort, is a premier destination offering world-class amenities and 1800 acres of breathtaking natural beauty. The resort features two renowned hotels, the Mauna Kea Beach Hotel, and The Westin Hapuna, sited on 2 of the best beaches in Hawaii along with two championship golf courses; including the newly imaged Robert Trent Jones course. Include oceanfront tennis courts and you understand the rarity of this offering. This 6,300-square-foot sanctuary offers six private bedrooms and six and a half baths, seamlessly blending Balinese, Chinese, and Hawaiian design elements into an architectural masterpiece. The separate 4 Bedroom Guest Villa ensures peaceful multigenerational living. Celebrated by Architectural Digest, this estate epitomizes refined island living. The property celebrates the Big Island’s indoor-outdoor lifestyle, with over 2,000 square feet of covered lanai spaces. Custom-designed outdoor showers enhance the tropical ambiance, while 200 degree panoramic ocean views, including Maui, elevate the estate's allure. An outdoor kitchen and dining pavilion, surrounded by tranquil Koi ponds, create an idyllic setting for entertaining or quiet reflection. The 80 ft infinity-edge pool connects the main hale to the primary suite and poolside pavilions. After the dramatic bridge entrance over koi ponds, you enter the Great Room with high ceilings and retractable pocket doors that open to meticulously landscaped gardens. The adjacent @4 acres of unbuildable common area adds to the absolute privacy of the estate. A complete solar array provides sustainable power, underscoring harmony with the environment. Discover Hawaiian elegance at Hale Kiekiena, between two white sand beaches—where luxury and natural beauty converge. Be sure to click on the camera and the Video icon at the top of the page...fabulous!

62-3680 Kiekiena Pl, KAMUELA

Listing courtesy of Aloha Sotheby's Intl Realty - Hawai'i.

$19,750,000
4 Beds ⋅ 5 Baths ⋅ 407563 MLS ⋅ Fee Simple Tenure
Basking in the breathtaking beauty of Maui, perched just 25 feet from the shoreline, 51 Hui Road E is more than an oceanfront estate – it is a living work of art. Built entirely in reinforced concrete and completed with precise craftsmanship, this timeless villa is as enduring as the island itself. Each pillar sinks deep into the volcanic foundation, giving this island masterpiece a quiet strength that mirrors the steady rhythm of the Pacific. Its proximity to the ocean can never be duplicated. The exotic architecture fuses Mediterranean grace with tropical ease. It celebrates both endurance and grace. It is a home designed, not merely to exist beside the ocean, but to belong to it – to draw strength from its power and beauty from its calm. Its most recognizable feature, a glowing orange palapa overlooking the ocean is perfect for casual outdoor living and dining. It offers surreal views of shimmering sunsets that stretch to the jewels of Lanai and Molokai as well as a serene vantage for watching whales in season. Steps away, the heated pool finished in mosaic tile mirroring the sea and an inset spa await. Garden pools, a koi pond, and lush, mature landscaping enhance the setting. Inside, the villa unfolds in layers of artistry and intimacy. The grand salon with its 17-foot vaulted ceilings, arched colonnades, Italian fountain, and romantic star shaped skylights set a tone of cultivated elegance. The chef’s kitchen discretely tucked away, honors traditional European service design – a private culinary domain outfitted with professional appliances, handcrafted cabinetry, and artisanal tile work. The primary suite is an ode to serenity. A four-poster bed faces an arched lanai framed in tropical vines opening to the sea beyond. Morning light spills across white stone floors while a hand-tiled fireplace and soft coastal hues evoke both romance and repose. In the adjoining bath, marble, crystal, and natural light converge. A soaking tub is framed by palms and ocean views. The library reveals the home’s most personal voice: coral-colored walls, a hand-painted ceiling, and imported carved wooden doors that open into a space of warmth. A place where art, books, and tropical light are in quiet harmony. A second wing includes guest accommodations, a magnificent wine storage area, and laundry facilities. Gates to the property open to a large motor court and garage with ocean views as well as custom work bench and additional storage. The immense substructure offers additional flexibility, not included in the living area square footage. Minutes from Kapalua Resort, yet entirely private, 51 Hui Road E stands as one of Maui’s most extraordinary oceanfront estates – where art, engineering, and the eternal rhythm of the Pacific meet in perfect harmony.

51 Hui Road E, Lahaina

Listing courtesy of Coldwell Banker Island Prop-KP.

Based on information from the Multiple Listing Service of Hicentral MLS, Ltd. Listings last updated on . Information is deemed reliable but not guaranteed. Copyright: 2026 by HiCentral MLS, Ltd. IDX information is provided exclusively for consumers' personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.