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3647 Diamond Head Road, Honolulu
$6,888,000
6 Beds ⋅ 7 Baths ⋅ 202603331 MLS ⋅ FS - Fee Simple Tenure
BREATHTAKING OCEAN VIEWS take center stage from the moment you step through the front doors of this elevated Spanish-style retreat at the base of world-renowned Diamond Head. Perched above neighboring homes, the property offers rare privacy, open sightlines, and the feeling of a private villa. Inside, graceful arched doorways, soaring ceilings, rich ohia wood floors, and beautiful carpentry reflect the home's timeless character. The layout features multiple living areas, a commercial-style kitchen with stainless steel counters, and three ocean-view bedroom suites with vintage bathrooms, and cedar-lined closets- offering a wonderful opportunity to update and personalize while honoring the home's original charm. Originally built by the Magoon family as a gathering space, the lower level includes two one-bedroom units and a studio, each with separate entrances and access to a shared laundry area. These spaces open to a lush, enclosed garden with fruiting trees and greenery, adding flexibility, income potential, a serene outdoor setting in one of Honolulu's most iconic locations.

3647 Diamond Head Road, Honolulu

Listing courtesy of Marcus Realty.

67 Wili Okai Way, Lahaina
$6,850,000
4 Beds ⋅ 4 Baths ⋅ 411404 MLS ⋅ Fee Simple Tenure
Nestled on what may be the finest parcel in all of West Maui, this expansive five-acre-plus sanctuary claims the premier position within Puunoa Estates. Thoughtfully designed landscaping combines with the property's naturally secluded setting to deliver complete seclusion. Within the exclusive, gated enclave of Puunoa only 24 estate properties exist, each spanning a minimum of five acres. The discerning owners who call Puunoa home have the means to reside anywhere globally, yet they've deliberately chosen this remarkable community. What draws them? An enviable lifestyle where perpetual summer weather meets effortless beach access, all framed by breathtaking vistas of the Pacific, neighboring islands, the West Maui Mountains, spectacular sunsets, and seasonal whale migrations. 67 Wili Okai Way stands apart with distinctive features rarely found among West Maui's current luxury offerings. The private entry drive makes a stunning first impression—majestic royal palms line the approach, framing spectacular mountain and ocean panoramas. An elegant water feature accented by tiki torches creates a welcoming threshold to this sophisticated single-story residence. The entire five-acre grounds showcase meticulous care, with indigenous flora, tropical plantings, and pristine emerald lawns throughout. The property's infrastructure allows for future expansion, including an ideal site for an Ohana cottage and a detached barn structure—both positioned to preserve the main residence's sweeping, uninterrupted views.

67 Wili Okai Way, Lahaina

Listing courtesy of Coldwell Banker Island Prop-KP.

4753 Aukai Avenue, Honolulu
$6,850,000
6 Beds ⋅ 6 Baths ⋅ 202618144 MLS ⋅ FS - Fee Simple Tenure
Offering a large property, situated in a cul-de-sac on coveted Aukai Avenue in Kahala. This is a rare opportunity to own this 13,500 sq.ft. lot with a 6,600+ sq.ft. interior home. A dramatic entry with soaring ceilings welcomes you into expansive interiors filled with natural light.Thoughtfully designed for gracious, entertaining and comfortable everyday living. The residence features warm natural wood accents, generous living spaces, a large gourmet kitchen, a desirable separate ground-floor suite, and recreation room. Outside, lush tropical landscaping, an expansive pool and spa create a serene setting for relaxation and gracious entertaining area complete with wet-bar and built-in BBQ. Enjoy the privacy, elegance, and appeal of one of the most desirable residential neighborhoods. A truly special island home offering privacy, scale and an extraordinary lifestyle two blocks from the ocean in Kahala. All just a few minutes away from The Kahala Hotel, Waiale Country Club, beach activities, dining and shopping.

4753 Aukai Avenue, Honolulu

Listing courtesy of Hawaii Modern Realty.

73-4476 Lemi Pl Unit 39, KAILUA KONA
$6,850,000
4 Beds ⋅ 5 Baths ⋅ 729531 MLS ⋅ ['Fee Simple'] Tenure ⋅ Hale Alani BLDG.
Hale ʻAlani 39 is a 4-bedroom, 4.5-bath residence with a detached guest house, sweeping views of the ocean, golf course, Hualālai Mountain, and Mauna Loa Mountain. Curated furniture package by award-winning designer Nicole Hollis, creates a cohesive and sophisticated interior aesthetic with expansive outdoor spaces. Inside, vaulted ceilings and rich, natural finishes create a warm yet contemporary ambiance. Basalt flooring anchors the main living areas, while the gourmet kitchen is appointed with a walk-in pantry, premium appliances, and a built-in Miele espresso machine. A dedicated wine room further elevates the home’s capacity for entertaining. The great room opens to the outdoors, where a distinctive layout positions the spa along the ocean-facing side and the pool to the north, creating separate yet equally inviting areas for relaxation. Just beyond the kitchen window, a tranquil water feature with lounge seating adds a serene focal point. An outdoor ENO gas grill and oven, anchors the alfresco dining experience, while tiki torches placed throughout the property lend a warm glow to evening gatherings. A detached guest ʻohana provides additional privacy and flexibility, complete with its own side yard, while a detached two-car garage with built-in cabinetry adds convenience. Sustainability and efficiency are supported by 40 solar panels and two Tesla Powerwall batteries. Hale ʻAlani 39 presents a rare opportunity to experience elevated island living, where thoughtful design, comfort, and natural beauty come together effortlessly. Kohanaiki is an exclusive private club and residential community along the Kona coast of Hawaii's Big Island, spanning 450 acres with a 1½-mile shoreline.

73-4476 Lemi Pl Unit 39, KAILUA KONA

Listing courtesy of Kohanaiki Realty LLC.

81-7870 Alii Dr, KEALAKEKUA
$6,830,000
2 Beds ⋅ 3 Baths ⋅ 730873 MLS ⋅ ['Fee Simple'] Tenure
ANALEA RANCH – A Rare Kona Coast Retreat Nestled along Hawaiʻi’s breathtaking Kona Coast, Analea Ranch is a 25-acre off-grid sanctuary offering privacy, sustainability, and panoramic ocean views. Rich in history and surrounded by natural beauty, this unique property blends modern self-sufficiency with the timeless charm of old Hawaiʻi. Property Highlights: * 25-acre private estate * Custom 2-bedroom cottage with wraparound lanai and ocean views * Fully off-grid with solar power, battery storage, backup generator, and a 30,000 gallon triple filteration water catchment system * Historic features including restored historic stone structures and traditional dry stack rock walls * Mature fruit and shade trees throughout the property * Detached garage, agricultural barn, multiple gazebos, and pickleball court * Ag-5 zoning with subdivision potential * Close to shopping, dining, medical facilities, and world-class ocean activities * Contiguous with Hokulia * Full set of architectural plans included * An Archaeological Inventory Survey * This property stands among the most unique offering on the Hawai'i Island A truly exceptional opportunity to own a private family retreat, agricultural estate, or legacy property for generations to come.

81-7870 Alii Dr, KEALAKEKUA

Listing courtesy of Corcoran Pacific Properties.

2661 Halalu St Unit A, KOLOA
$6,790,000
8 Beds ⋅ 11 Baths ⋅ 730152 MLS ⋅ ['Fee Simple'] Tenure
Exceptional Income-Producing Opportunity in Poʻipū Beach Estates. Located in the highly sought-after Poʻipū Beach Estates community, presents a rare opportunity to acquire a high-performing vacation rental property on approximately 1.09 acres in the heart of Kaua‘i’s South Shore. Currently generating about $750,000 per year in gross vacation rental bookings, this property offers strong existing cash flow and exceptional investment potential. The property features four separate structures designed to maximize occupancy and flexibility: One 4-bedroom, 4.5-bath Balinese style home with four primary bedrooms each with its attached bathroom and private lanai. Fully air-conditioned home also includes full kitchen, dining and living areas, patio with grill and washer/dryer. One 4-bedroom, 4-bath brand new home with four primary bedrooms with attached bathrooms and one large lanai for family gathering. Fully air-conditioned home also includes full kitchen, dining and living areas, patio with grill and washer/dryer. Two detached 2-car garage structures that can be used as additional non-rentable storage space, each including a loft, bathroom, sun deck, AC and washer/dryer. The versatile layout accommodates a variety of living and rental configurations, making it ideal for large groups, multi-generational travelers, or extended stays. The expansive grounds and beautiful, lush landscaping provide privacy and separation between structures while maintaining a cohesive estate-style setting. This estate has a total of 8595 sf of useable space, 5405 sf of interior air-conditioned space, 3985 sf living space, and 2033 sf lanai space. Positioned minutes from Poʻipū’s beach, golf courses, shopping, restaurants, this property is in one of Kauai's most desirable communities.

2661 Halalu St Unit A, KOLOA

Listing courtesy of Coldwell Banker Island Properties - Kauai.

75-101 Lolo Ln, HOLUALOA
$6,750,000
7 Beds ⋅ 9 Baths ⋅ 733932 MLS ⋅ ['Fee Simple'] Tenure
AWE-INSPIRING LUXURY RESORT STYLE ESTATE OUTSIDE OF RESORTS! BREATHTAKING AND DISTINCTIVE! AN EXCEPTIONAL 6 ACRE ESTATE WITH A 1/1 GUEST HOUSE, POOL/SPA , AND SENSATIONAL OCEAN VIEWS! A STUNNING PARK - LIKE SETTING! LUXURY LIVING COMPLETELY REDEFINED! An extraordinary 6 bed/6.5 bath residence awaits, as you enter the beautifully custom gated driveway, long and sleek, lined with commanding Royal Palms. Enter this luxury estate of amazing beauty with custom finish and architecture in every direction, as you are embraced by the magnificent Ocean and Kailua Bay views just in front of you! The rooms are big and bold with the richness of deep mahogany, high ceilings and stunning beams. The impeccably designed gourmet kitchen is rich in cabinetry, leather type granite countertops, and luxury appliances, a chef's dream! The primary suite is breathtaking, in addition all 5 bedrooms are en suites. All bathrooms are beautifully appointed. Powerful yet gracious, warm and welcoming, this estate blends with the natural beauty of the island, plenty of space and a feeling of exclusivity throughout! This beautiful estate property includes an infinity pool with a spa, stunning fountain features, a wine room, enormous lanai's covered in rich Ironwood, lush and well maintained landscaping in every direction, a wonderful variety of flowers, fruit trees, coffee and so much more. A charming 1/1 separate guest home with its own gated entrance and a 2 car garage, is a great place to offer to extended guests and family. This lovely 6 acre estate surrounded with paved walking/golf cart paths for your pleasure, encompasses a true Hawaiiana feeling with a richness and warmth that gives you a feeling that you have arrived! Approximately 12 minutes to Kona town, an ideal location tucked away in tropical privacy. Great elevation. Come and own this luxury estate dream property, a piece of Hawaiian paradise!

75-101 Lolo Ln, HOLUALOA

Listing courtesy of Premier Island Properties LLC.

4821-L Koloa Rd, KOLOA
$6,750,000
4 Beds ⋅ 5 Baths ⋅ 734132 MLS ⋅ ['Fee Simple'] Tenure ⋅ Omao Ranch Lands BLDG.
Welcome to Iron Gate Ranch, an unrivaled equestrian estate where ultimate privacy, refined luxury, and modern sustainability converge on Kauai’s coveted South Shore. Encompassed behind a gated entrance on over 11 sprawling acres of prime agricultural land, this secluded compound offers a rare blend of tranquil island seclusion and incredible convenience, situated just five-minutes from the world-class beaches and resort amenities of Poipu Beach. At the heart of the estate sits an expansive, 4,200+-square-foot single-story residence designed to embody effortless indoor-outdoor living. The home offers four ensuite bedrooms—each with its own walk-in closet and direct exterior access. An impressive great room and an adjacent indoor/outdoor/wellness space, (including sauna and cold plunge) both open gracefully to a resort-style pool, spa and fire pit, creating an ideal backdrop for relaxation or entertaining. Designed for effortless living, the estate seamlessly blends cutting-edge technology with sustainable luxury. Energy independence is powered by a 38-panel photovoltaic solar array paired with a Tesla Powerwall battery backup system. Complete home control is provided through a state-of-the-art Savant automation system with an integrated Sonos sound system, while a six-zone central climate control system delivers year-round indoor comfort. Beyond the main residence, the estate includes dedicated equestrian facilities, multiple fruit trees, and plenty of space for agricultural pursuits. The property also offers the ability to construct an additional 1,000-square-foot secondary dwelling along with supplementary agricultural buildings. Whether envisioned as an active equestrian compound, a self-sustaining private sanctuary, or an expandable multi-generational estate, this landmark property offers an extraordinary lifestyle on Kauai.

4821-L Koloa Rd, KOLOA

Listing courtesy of COMPASS.

68-222 Olohio Street, Waialua
$6,750,000
3 Beds ⋅ 3 Baths ⋅ 202615832 MLS ⋅ FS - Fee Simple Tenure
Situated on over 2 acres of beautifully landscaped grounds, this 3-bed, 3-bath home offers exceptional privacy, expansive living and family rooms, and an oversized primary suite complete with an ensuite bath, walk-in closet, and dedicated office. A newly tiled pool with jacuzzi invites you to fully embrace the island lifestyle. The front yard orchard boasts avocado, mango, Tahitian lime, Meyer lemon, grapefruit, oranges, dragon fruit, and more, while the backyard showcases a striking ponytail palm, stately monkeypod trees, and a variety of well-established shade trees. Additional highlights include a 4-car epoxy-coated garage, ample guest parking, and expansive open areas ideal for entertaining. Perfectly positioned near secluded beaches offering year-round surfing, fishing, and diving, the property is also close to Dillingham Airfield (private planes), seasonal polo matches, and Haleiwa Harbor (boat storage). Bonus: Dual Zoning - Agricultural and Residential - keeps water bills around $46/month and property taxes near $9,000/year. This rare North Shore retreat offers the perfect blend of space and serenity.

68-222 Olohio Street, Waialua

Listing courtesy of Engel & Volkers Honolulu.

3275 Kalihiwai Rd Unit B, KILAUEA
$6,749,000
4 Beds ⋅ 4 Baths ⋅ 733840 MLS ⋅ ['Fee Simple'] Tenure ⋅ Mele O Ke Kai Condo BLDG.
Mele O Ke Kai – “Song of the Sea” | North Shore, Kauai Perched above the Kalihiwai River Valley with sweeping views of Bali Hai, Mount Waialeale, and the Namahana Mountains, this private, gated Unit B residence blends contemporary island living with timeless craftsmanship. Set within the two-unit Mele O Ke Kai CPR, the approximately 2.5-acre offering provides a peaceful North Shore retreat. The main residence features expansive lanais for seamless indoor–outdoor living, custom wood cabinetry, quartz counters, and Cumaru hardwood floors. A new roof and a 40-panel solar system with four backup batteries complement the home's thoughtful improvements. A private guest suite below offers flexibility for visitors or extended family, while two laundry rooms—one upstairs and one downstairs—add everyday convenience. A custom copper gate welcomes you to lush tropical landscaping accented by a mango tree and citrus trees. Enjoy easy access to Anini Beach, the Kalihiwai River, nearby dining, golf, and the natural beauty of Kauai's North Shore. This offering includes Unit B only, TMK 4-5-3-003-052-0002.

3275 Kalihiwai Rd Unit B, KILAUEA

Listing courtesy of Coldwell Banker Island Properties.

344 Lama Place, Kailua
$6,650,000
4 Beds ⋅ 4 Baths ⋅ 202612902 MLS ⋅ FS - Fee Simple Tenure
Experience breathtaking Mokulua Islands views from every corner of this Lanikai hillside home. The home offers head-on, unobstructed views of the Mokes, with the sea & coral shifting colors from sunrise to sunset, while the elevated lanai frames a front-row seat to the ocean's daily rhythm—paddlers, sailboats, and passing whales in winter. Tucked away on a quiet, dead-end street, the home is a true oasis that is away from the busy loop and above the tsunami evacuation zone, while being only a few minutes walk to the beach. A fully fenced yard and separate entrances into the home make the property ideal for any lifestyle—entertaining, children, pets, or multi-generational living. The floor plan offers several options for a quiet home office away from other living areas, providing flexibility. Fruit-bearing trees surrounds the home, butter avocado, mango, coconut, fig, tangerine and lemon. Beyond its beauty, there may be opportunity for upside: sitting below the current building height limit and with a generously sized lot, options abound. A rare blend of privacy, panoramic head-on Mokes views, an extra-large lot, and future flexibility awaits in this Lanikai hillside sanctuary.

344 Lama Place, Kailua

Listing courtesy of OahuRE.com.

235 Portlock Road, Honolulu
$6,500,000
7 Beds ⋅ 6 Baths ⋅ 202528543 MLS ⋅ FS - Fee Simple Tenure
Tucked behind a gate in prestigious Portlock, this extensively remodeled home offers rare privacy and peace, just a two-minute walk from the beach. Thirty-foot sliding glass doors span the full width of the house and open to a large covered lanai and backyard with a 50-foot saltwater pool and spa. Mature palms along the property line keep the yard secluded. Step through the front door into expansive living spaces with soaring ceilings. The layout includes seven bedrooms, with two large primary suites that each have a private lanai and a luxurious marble bath. A spacious first-floor bedroom-studio with a private entrance, sauna, and kitchenette adds flexibility for guests, a home office, or separate living space. It all sits on a 13,000+ sq ft lot with ¼ shared ownership in a beach access walkway. Costco and two large Hawaii Kai shopping centers, with plenty of restaurants and shops, are a four-minute drive away. Close to the beach, close to everything, in one of the island's most established coastal neighborhoods. Owner financing available.

235 Portlock Road, Honolulu

Listing courtesy of Keller Williams Honolulu.

81 Iliahi Way Unit A, Lahaina
$6,495,000
5 Beds ⋅ 5 Baths ⋅ 411069 MLS ⋅ Fee Simple Tenure
Located nearly 1,000 feet above the Pacific at the top of tranquil Launiupoko, 81 Iliahi is a West Maui landmark that has been thoroughly cared for and updated in recent years. This secluded 35.7-acre estate delivers a rare combination of scale, privacy, and 180-degree ocean views, with Lanai and Molokai stretching across the horizon. The four-bedroom main residence and separate cabana bedroom offer 4,670 sq. ft. of living space and five bathrooms. Warm wood finishes, natural stone, and wide openings frame the landscape, while generous covered lanais open to the gardens, infinity-edge pool, and hot tub. Living spaces face the ocean, sunsets, and the outer islands, and the elevation creates a gentle, cooler microclimate. The estate has been refreshed inside and out. Big-ticket items include a new standing seam metal roof on every building, fresh exterior paint on the house, cabana, and garage, and new glass and screens in every sliding door. Comfort upgrades include new A/C in the main living area, cabana, and office, new laminate flooring in three bedrooms, and replaced patio ceiling fans. The water systems have been extensively renewed, with new potable and agricultural tank liners, new pumps and motors, and upgraded irrigation controls. A monitored security system, remote cameras, and Wi-Fi gate controls can all be managed by voice or phone. The pool has a passive solar heater, new filter, and low-voltage landscape lighting, and the fruit orchard has been freshly cleared and mulched. The pool cabana, with a wet bar, beverage fridge, separate bathroom, and outdoor shower, adds convenience and flexibility to this one-of-a-kind estate. Launiupoko Beach Park and West Maui’s shops, dining, and amenities are just minutes away. 81 Iliahi is one of Maui’s most distinctive hillside estates: private, well-maintained, and defined by its views. The property features a detached second structure reflected in County records as approximately 444 square feet with 0 bedrooms and 1 bathroom. This listing is a Residential CPR.

81 Iliahi Way Unit A, Lahaina

Listing courtesy of Welcome Hawaii Properties.

2999 Kaohe Rd, KILAUEA
$6,495,000
4 Beds ⋅ 3 Baths ⋅ 731147 MLS ⋅ ['Fee Simple'] Tenure
Some properties are only experienced, once you're here, you may never want to leave. I can confidently say that no photograph can possibly capture the extraordinary feeling of sitting beneath the gazebo, perched on the bluff, overlooking your own private world. It is a place that engages every sense. You have arrived. Listen to the rhythmic symphony of the surf as waves crash against the rocks across Kalihiwai Bay. Breathe the fresh ocean air carried by the trade winds. Watch the ever-changing sky, shifting light, and endless shades of blue stretching across the bay and coastline. The experience is nothing short of mesmerizing. From this remarkable vantage point, you'll enjoy sweeping views of Kalihiwai Bay, the dramatic coastline, the open Pacific, and, after sunset, the soft twinkle of lights from homes across the bay. It's a setting that invites you to slow down, unwind, and simply take it all in. . The meticulously maintained four-bedroom cottage complements its spectacular setting with timeless island character, warmth, and charm. Rather than competing with the natural beauty, it embraces it, creating a home where the views, the sounds, and the serenity become part of everyday life. This is more than a home—it's one of those rare places that reminds you why people dream of Kauai.

2999 Kaohe Rd, KILAUEA

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

59-355 Ke Nui Road, Haleiwa
$6,350,000
5 Beds ⋅ 4 Baths ⋅ 202604789 MLS ⋅ FS - Fee Simple Tenure
Experience the ultimate beachfront lifestyle at the world-renowned Banzai Pipeline, where surf history and stunning natural beauty collide. This architect-designed home captures the essence of seamless indoor–outdoor living, with airy, open-concept interiors flowing effortlessly onto expansive lanais. Upstairs, three serene bedrooms and two baths provide a front-row seat to Pipeline’s barreling surf, white-sand beach, and glowing sunsets. The versatile lower level offers two additional bedrooms, two baths, a full kitchen, and spacious living and dining areas perfect for hosting loved ones or accommodating multi-generational living. With over 50 feet of private beachfront, a lush, manicured yard, and a covered lanai, this property is an entertainer’s paradise, made even more convenient with a motorized gate and parking for up to eight vehicles. Nestled in the heart of the North Shore’s most coveted neighborhood, this home isn’t just a residence—it’s a rare retreat where every day begins with the soothing sound of the surf and ends with unforgettable sunsets. Opportunities like this are scarce—claim your place on one of Hawaii’s most iconic stretches of coastline.

59-355 Ke Nui Road, Haleiwa

Listing courtesy of Compass.

69-1648 Puako Beach Dr, KAMUELA
$6,315,000
3 Beds ⋅ 3 Baths ⋅ 729949 MLS ⋅ ['Fee Simple'] Tenure
An excellent value in an Island location everyone dreams about! Currently an active vacation rental, this inviting Puako oceanfront home is located within steps of a small sandy beach and easy access to the ocean and reef! Outstanding expansive ocean, coastline, Maui and sunset views! This resort quality ,well designed home offers the comfort and beauty of oceanfront and beach living. 2 master suites with ensuite baths and private lanai's offer privacy. The spacious living area flows into a covered lanai creating additional living space open to the beach access. The design works very well as a vacation rental(STVR permit is active and transferable) and can easily adapt itself to be a primary residence or perfect second home. This beautiful, turnkey home is found in a prime location within this well known residential oceanfront community. Puako is its own wonderful oasis on the Gold Coast of the Big Island between world -class resorts and all they have to offer.

69-1648 Puako Beach Dr, KAMUELA

Listing courtesy of Hapuna Realty.

4871 Lower Honoapiilani Rd, Lahaina
$6,300,000
6 Beds ⋅ 7 Baths ⋅ 411320 MLS ⋅ Fee Simple Tenure
AUCTION: Bidder registration deadline: 1 December. Starting bids expected between $2.5M–$3.5M. Set along the Kahana coastline, this oceanfront estate pairs sweeping Pacific views with a gracious two-story layout, enhanced by six-figure cosmetic updates completed in 2026. Dual primary suites on the upper and lower levels offer comfort and privacy, while an elevator rises to a media and game room beside the upper primary suite. Private caretaker’s quarters add welcome flexibility for staff or guests. Outdoors, an in-ground pool and hot tub frame the ocean panorama, complemented by a workshop and three-car garage. Kapalua’s championship Plantation and Bay golf courses, celebrated surf breaks, pristine beaches, and acclaimed dining are all just minutes away, completing an effortless West Maui lifestyle. Offered unfurnished and excluding artwork.

4871 Lower Honoapiilani Rd, Lahaina

Listing courtesy of Coldwell Banker Island Prop-KP.

3330 Tantalus Drive, Honolulu
$6,300,000
3 Beds ⋅ 2 Baths ⋅ 202605681 MLS ⋅ FS - Fee Simple Tenure
A rare opportunity to acquire an incredible Honolulu estate. Built in 1908 by Alfred Castle, this remarkable 13+ acre Tantalus property has been held by just four distinguished families, Castle, McCandless-Marks, Dillingham lineages, and the estate of Juan Hamilton—renowned artist and protégé of Georgia O’Keeffe. A stately drive welcomes you with eucalyptus trees where expansive lawns evoke the elegance of a bygone era and invite grand outdoor gatherings. Panoramic views from Diamond Head to Haleiwa showcase striking sunsets over the Pacific. Fragrant puakenikeni, jasmine and white ginger bloom amid a landscape of moss rock walls, brick pathways, and wooded trails. The buildings are rich with historic details and distinctive architectural finishes. A 60,000-gallon water catchment system underscores the estate’s blend of heritage and stewardship. More than a residence, this is a landmark property awaiting its next chapter—a chance to reimagine one of Honolulu’s great estates. For those drawn to the intersection of history, nature and place, this extraordinary offering represents far more than real estate. It is a legacy to inherit, shape, and preserve for generations to come.

3330 Tantalus Drive, Honolulu

Listing courtesy of Compass.

948 Kai Hele Ku St Unit Unit A, Lahaina
$6,300,000
5 Beds ⋅ 6 Baths ⋅ 409968 MLS ⋅ Fee Simple Tenure
Set on over 2 acres in Launiupoko, one of West Maui's most prestigious hillside communities, this stunning single-story estate offers 5 bedrooms (4 bedrooms + 1 bedroom pool cabana), 5.5 bathrooms, and 4,291 square feet of refined Hawaiian contemporary living. Perched on a breathtaking West Maui hillside in prestigious Launiupoko, this luxury residence boasts some of the most dramatic sunset and outer island views on the island, a resort-style pool and spa, and the kind of indoor-outdoor flow that makes every day feel like a vacation.  Arriving through a grand hardwood entry door framed by lush tropical landscaping, the foyer sets a tone of relaxed sophistication, with clean lines, Imperial plaster walls, and wide-plank Pasha Wood Lite tile underfoot. The great room opens dramatically, with walls of glass pocket doors that retract fully to merge the interior living space with the covered lanai beyond. Ocean views pour in from every angle. The seamless indoor-outdoor flow is not an afterthought here; it is the central design ethos. The gourmet kitchen is a showpiece in its own right. Custom cabinetry pairs with granite countertops and a generous center island with bar seating. A stainless range with a statement hood anchors the space, while pendant lighting and a picture window framing the Pacific and the silhouette of Lanai on the horizon make this a kitchen where cooking becomes an event. The open dining area flows naturally off the kitchen, ideal for entertaining at any scale. The primary suite is a sanctuary. Sliding glass doors open directly onto the pool deck, and ocean views greet you from bed each morning. Rich oak millwork, ceiling fans, and thoughtful finishes are found throughout all four bedrooms. Step outside and the property reveals its full ambition. A resort-style lap pool stretches across the rear of the home, glowing blue against the warm Maui sky at dusk. An elevated spa sits alongside, with travertine decking, manicured tropical lawn, and swaying palms completing the scene. The private pool cabana adds a layer of luxury rarely found at this price point, offering a full bath and outdoor shower for seamless poolside living.  A built-in outdoor kitchen and covered lanai dining area make alfresco entertaining effortless, with front-row sunset views over the ocean and the outer islands of Lanai and Molokai as the backdrop. Owned photovoltaic solar, solar water heating, central air, and a 3-car garage round out an estate that performs as beautifully as it looks. This is Launiupoko living at its absolute finest! This listing is a Residential CPR.

948 Kai Hele Ku St Unit Unit A, Lahaina

Listing courtesy of Welcome Hawaii Properties.

3210 Diamond Head Road Unit 4, Honolulu
$6,295,000
4 Beds ⋅ 4 Baths ⋅ 202619936 MLS ⋅ FS - Fee Simple Tenure ⋅ Leahi Estates BLDG.
Welcome to one of Diamond Head's most unique and architecturally distinctive homes. Designed by award-winning architect Norman Lacayo and perfectly positioned on the ocean-facing slopes of Diamond Head, this incredible residence offers breathtaking ocean views, spectacular sunsets, and exceptional privacy. Featuring over 3,200 square feet of interior living space, expansive covered lanais, soaring ceilings, and beautiful custom woodwork, the home was designed to take full advantage of its remarkable surroundings. The thoughtfully designed multi-level layout seamlessly connects indoor and outdoor living, while the private pool area, surrounded by lush tropical landscaping and a beautiful waterfall, feels like a magical retreat of its own. Check the surf right from your home, walk over to Leahi Park for morning yoga, or simply relax and enjoy the incredible surroundings. Just minutes from Waikiki, Kapiolani Park, and some of Oahu's most iconic beaches, this is a truly one-of-a-kind property. MLS and tax records may vary. Buyers to do their own due dilligence.

3210 Diamond Head Road Unit 4, Honolulu

Listing courtesy of Real Broker.

68-118 Pukaua Pl, KAMUELA
$6,250,000
4 Beds ⋅ 5 Baths ⋅ 724360 MLS ⋅ ['Fee Simple'] Tenure
Newly Completed Luxury Residence. County and HOA final approvals received 8.20.26 Welcome to 68-118 East Pukaua Place, an exquisite luxury estate nestled within the exclusive Champion Ridge community of Mauna Lani Resort on the Big Island. This gated enclave comprises 35 half-acre lots, offering unparalleled privacy and prestige. This newly constructed four-bedroom, five-bathroom home boasts over 3,200 square feet of seamless indoor-outdoor living, embodying the ultimate resort-style experience. Enjoy breathtaking panoramic views of Hualalai, Mauna Kea, Mauna Loa and the Kohala Mountain ranges, complemented by stunning ocean and sunset views framed by the distant backdrop of Haleakala. Designed with meticulous attention to detail, the estate features dual primary suites on each level, complete with spa-like en-suite bathrooms. Two additional private guest bedrooms ensure ideal comfort and privacy for visitors or rental guests. Open-concept living and dining areas flow effortlessly onto expansive lanais through pocket doors, creating perfect outdoor entertainment spaces unique to island living. The gourmet chef's kitchen is a culinary dream, equipped with high-end appliances and custom cabinetry. Soaring vaulted ceilings, thoughtfully designed interior finishes, and meticulous craftsmanship elevate the home's luxurious appeal. Located within the gated Champion Ridge community, this residence provides access to Mauna Lani’s world-class amenities. Indulge in championship golf courses, the exclusive Mauna Lani Beach Club with its private beach and oceanfront dining, and the upscale Shops at Mauna Lani offering fine dining, shopping, and a gourmet market. With its short-term vacation rental (STVR) permit, this property offers exceptional flexibility, serving as a primary residence, a luxurious second home, or a lucrative investment opportunity. *Seller is also considering the option of a 25% co-ownership interest sale for $1,715,000

68-118 Pukaua Pl, KAMUELA

Listing courtesy of eXp Realty.

3307-A Pohaiula Pl, LIHUE
$6,200,000
4 Beds ⋅ 6 Baths ⋅ 732249 MLS ⋅ ['Fee Simple'] Tenure
Nestled in Lihue’s exclusive Hokuala resort community, this brand-new 5,160 sq ft bespoke residence sits on a nearly ¾-acre lot and offers nearly 2,000 sq ft of outdoor living plus a private pool - ideal for relaxed island gatherings and elevated everyday living, with the convenience of an in-town location. Thoughtful details and timeless materials create understated luxury throughout. A striking fireplace anchors the main living area beneath the soaring two-story ceiling, complemented by a custom glass staircase. Large-format tile floors flow seamlessly indoors and out, while natural wood flooring warms the bedrooms. The gourmet primary kitchen, butler’s pantry, and robust outdoor kitchen feature quartzite counter and a full-suite of Thermador appliances, including a range, secondary cooktop, built-in refrigeration, wine storage, steam oven, speed microwave, dishwashers, ice maker, and built-in coffee system. Designed for comfort and privacy, the home offers four generously appointed en-suite bedroom suites. The upstairs living room and lanais capture the mountain and ocean views, and the poolside flex room with wet bar adapts as a gym, wellness space, cabana, or guest suite. Fully furnished and move-in ready with refined furnishings and decor, this coastal sanctuary feels polished, distinctly Kauai, and ready for enjoyment as a primary residence, second home, or vacation rental property. Located in the Visitor Destination Area (VDA), nightly short-term rentals are allowed. As part of the Pakela Ike neighborhood in the 450-acre Hokuala community, Hokuala Club Membership privileges ownership include access to the 18-hole Ocean Course, pickleball and tennis courts, 16-acre organic farm, lagoons, 13+ miles of trails, adventure gear, preferred pricing at Hualani’s Restaurant and Nanea Spa, wildlife sanctuary, and owner events - all just minutes from everything that Kalapaki Bay and Lihue has to offer. Video: https://tinyurl.com/3307Pohaiula

3307-A Pohaiula Pl, LIHUE

Listing courtesy of Hawaii Life.

72-4067 Ke Ana Wai St, KAILUA KONA
$6,000,000
4 Beds ⋅ 5 Baths ⋅ 728026 MLS ⋅ ['Fee Simple'] Tenure
Modern Luxury Awaits at Makalei Estates/ Under construction Unrivaled Customization Meets Island Elegance Seize the rare opportunity to own a masterfully designed contemporary estate in the prestigious Phase II of Makalei Estates. Currently under construction, this 5,800 sq. ft. sanctuary offers a sophisticated floor plan blending architectural boldness with the beauty of the Kona Coast. By securing this residence now, the buyer is invited to collaborate on the selection of final finishes, ensuring the home is a bespoke reflection of their personal style. Sophisticated Living Spaces: Grand Interior: Boasting 4 expansive bedrooms and 4.5 spa-inspired baths, the home is divided into a magnificent Main House and a private Guest Wing. Entertainment Hub: Transition from a day in the sun to an evening in your professional-grade Theater Room, designed for ultimate cinematic immersion. Culinary Excellence: A chef’s kitchen featuring a massive island and high-end cabinetry flows seamlessly into the Great Room. The Ultimate Outdoor Oasis: Infinity Living: Step outside to a world-class infinity-edge pool and spa, meticulously positioned to offer unobstructed, panoramic ocean views. Expansive Lanais: Enjoy 2,500 sq. ft. of covered lanai space, including dedicated dining and lounging zones perfect for Kona’s famous sunsets. Masterful Landscaping: The property is anchored by extensive, hand-crafted lava rock retaining walls and an expansive, level yard that maximizes the 3.3-acre lot. Premium Infrastructure Spacious Storage: An oversized 3-car garage provides ample room for vehicles and island toys. Artful Engineering: From the gated entry to the detailed masonry, every inch of this Lot 20 estate reflects the highest standards of modern engineering and design. Don't just buy a home—design your lifestyle. Contact us today to review the permit plans and begin selecting the finishes for your North Kona dream estate.

72-4067 Ke Ana Wai St, KAILUA KONA

Listing courtesy of Coldwell Banker Island Properties - Kona.

671 Kahiau Loop, Honolulu
$5,999,999
5 Beds ⋅ 5 Baths ⋅ 202616928 MLS ⋅ FS - Fee Simple Tenure
We invite you to discover a home built for legacy—where family stories flourish and generations thrive. Perched within gated Hawaii Loa Ridge on a double rim lot, this Mediterranean-inspired estate commands sweeping, unobstructed views of the ocean, Diamond Head, and the coastline. Sunsets here are nothing short of breathtaking. This 5-bedroom, 4.5-bath residence showcases premium materials imported from Greece and Germany, offering timeless elegance and understated sophistication. Soaring ceilings and abundant windows bathe every room in natural light, with views from nearly every major space.The primary suite is a private retreat, featuring a 400 sq ft lanai, jacuzzi tub, and walk-in closets. The gourmet kitchen, with German cabinetry, opens to a breakfast nook overlooking the sparkling pool and spa. Outside, the pool deck is ideal for entertaining, while the manicured tropical backyard includes an 880 sq ft sport court. Parking for 3+ cars and 24-hour security complete the offering.We would be honored to host your private showing. May this residence become the heart of your family's enduring legacy—warmth, prosperity, and grace, for generations to come. All offers are welcome!

671 Kahiau Loop, Honolulu

Listing courtesy of Five Star Realty, Inc..

2211-A Pane Rd, KOLOA
$5,999,999
4 Beds ⋅ 3 Baths ⋅ 731848 MLS ⋅ ['Fee Simple'] Tenure
$500k IN DOCUMENTED HISTORICAL ANNUAL GROSS RENTAL REVENUE available upon request. NO HOA! The LOCATION right across the street from Brennecke's Beach does not get any better. It's not just the amazing location, the spectacular ocean views and the income, it’s the rarity of finding a large R-4 corner lot inside the Visitor Destination Area with potential for a future ADU expansion, an already installed second water meter and a home built with craftsmanship, the highest quality materials and attention to detail.   A home thoughtfully created to enjoy one of Kauai's most treasured locations where the South Shore lifestyle comes alive in a way that is difficult to replicate and impossible to forget.   Imagine beginning each morning with your beverage of choice on the spacious screened lanai overlooking the Pacific Ocean as the envigorating trade winds flow through. The day unfolds relaxed with a swim in crystal-clear water, breakfast at home or Brunch at the Grand Hyatt two miles away at the end of the Greenbelt that starts right in front of your home and the afternoon on the golf course. By sunset, everyone has found their way back home, gathering by the all-tile heated pool, sharing memories beneath the ever-changing multicolor Hawaiian sky.   A rare opportunity to own a home with provenance, the personal residence of accomplished architect Leslie Stone known in California for his advocacy for open spaces. A home with expansive windows framing 180 degrees of ocean views, skylights filling the interiors with natural light, and windows throughout blurring the line between indoors and out. Built without compromise with enhanced roof framing, carefully selected materials and designed specifically for this exceptional coastal setting. Many of these details remain unseen, yet they speak to the care and intention invested in every detail at every stage of construction. ~Walk through (cut & paste): https://my.matterport.com/show/?m=YWT6mEKx2tf&

2211-A Pane Rd, KOLOA

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

530 Mahana Ridge St, Lahaina
$5,995,000
4 Beds ⋅ 4 Baths ⋅ 411367 MLS ⋅ Fee Simple Tenure
Located within Mahana Estates in Kapalua, 530 Mahana Ridge Street is a brand-new luxury residence awaiting its first lucky owners. Set on 1.8 glorious acres, the single-level residence features 4 bedrooms, 4 bathrooms, and 3,243 square feet of interior living space, complemented by 938 square feet of covered lanai and 452 square feet of uncovered outdoor living areas The estate is a meditation in fine living, combining seclusion, generous living spaces, and sweeping views across the Pacific Ocean to the emerald cliffs of Moloka?i. An in-ground swimming pool and spa create a private outdoor retreat framed by dramatic ocean and island views. Additional features include an 872-square-foot, three-car garage, owned photovoltaic system, and central air conditioning. With its brand-new construction, the residence presents a rare opportunity to be the first to call this beautiful Kapalua property home. Beyond the residence, Kapalua offers one of Maui’s most celebrated resort lifestyles. Mahana Estates residents benefit from an access easement through the Ritz-Carlton property connecting to D.T. Fleming Beach and nearby golf amenities. The renowned Plantation Course, championship golf, coastal trails, and luxurious Spa Montage contribute to the appeal of this exceptional community. Optional membership in the Kapalua Club provides opportunities for additional resort privileges, including spa and beach club access and preferred golf benefits, subject to membership terms. With its expansive homesite, panoramic ocean and island views, brand-new luxury construction, and access to Kapalua’s beaches, golf, dining, and resort amenities, 530 Mahana Ridge Street is ready to welcome its first owners to an extraordinary Maui lifestyle.

530 Mahana Ridge St, Lahaina

Listing courtesy of Welcome Hawaii Properties.

4240 Kaikoo Place, Honolulu
$5,995,000
5 Beds ⋅ 6 Baths ⋅ 202618082 MLS ⋅ FS - Fee Simple Tenure
SHORT SALE…. A rare opportunity to own one of Diamond Head's most captivating oceanfront estates at amazing price; truly the best value Diamond Head. This Balinese-inspired masterpiece blends timeless island elegance with modern sophistication. Designed to embrace Hawaii's indoor-outdoor lifestyle, the residence opens seamlessly to panoramic ocean vistas and the rhythmic sound of the waves. This five-bedroom sanctuary showcases bespoke finishes, natural textures, and an architectural flow that evokes both serenity and grandeur. The primary suite offers breathtaking ocean views and a spa-like en-suite retreat, while a private guest apartment-complete with its own entrance-provides stunning views of Diamond Head and total privacy for family or guests. Outdoors, a private tropical oasis awaits. Surrounded by lush landscaping, the grounds feature a resort-style pool, elevated spa, fire pit, and tranquil koi pond, creating an atmosphere of peaceful indulgence. Gated and secure, yet minutes from Waikiki Beach and Diamond Head State Monument, this rare offering perfectly balances luxury, seclusion and convenience. it is the premier value in Diamond Head's pristine oceanfront enclave.

4240 Kaikoo Place, Honolulu

Listing courtesy of RE/MAX Honolulu.

68-1002 Hoe Uli Way, KAMUELA
$5,950,000
6 Beds ⋅ 6 Baths ⋅ 734377 MLS ⋅ ['Fee Simple'] Tenure
A modern tropical residence set within the Mauna Lani resort community, designed for unhurried resort living on Hawaii Island. A rare opportunity to own a six-bedroom, six-bath residence with verified short-term vacation rental eligibility, offering exceptional flexibility and income potential. Approximately 3,401 square feet of living space on a generous 17,174-square-foot lot. Walnut custom cabinetry, natural quartzite countertops, and wood-beam ceiling details. New designer furnishings! Hawaii's indoor-outdoor lifestyle, featuring private bedroom wings surrounding a tropical courtyard, with expansive glass doors connecting the great room, dining area, and kitchen to the spacious poolside lanai. A private swimming pool and spa, outdoor kitchen, natural stone accents, and lush tropical landscaping. Energy-saving solar photovoltaic panels, battery storage, and a car charger. Nohea residents enjoy their own beautifully landscaped, on-site private amenity center featuring a free-form swimming pool, heated spa, fitness hale, gathering clubhouse with full kitchen, and two poolside BBQ pavilions. The renowned Mauna Lani Resort offers an extraordinary collection of amenities, including access to the Mauna Lani Private Beach Club with white sand, calm waters ideal for snorkeling and paddleboarding, beachfront lounging, and oceanfront dining at Napua Restaurant. Enjoy two championship golf courses, scenic coastal trails, historic Hawaiian fishponds, The Shops at Mauna Lani, and exceptional dining and spa experiences at the Mauna Lani Auberge and Fairmont Orchid resorts. An outstanding opportunity to own a brand-new luxury residence in one of the Kohala Coast's most desirable resort communities with views of the Mauna Lani golf course. Estimated completion: December 2026, subject to construction schedule. Artist's renderings illustrate the proposed design; finishes and landscaping are subject to change. Ideal vacation rental setup.

68-1002 Hoe Uli Way, KAMUELA

Listing courtesy of Better Homes and Gardens Real Estate Island Lifestyle.

44-375 Kaneohe Bay Drive, Kaneohe
$5,950,000
3 Beds ⋅ 2 Baths ⋅ 202606682 MLS ⋅ FS - Fee Simple Tenure
A rare opportunity to create a legacy waterfront estate on one of Kaneohe Bay’s most exceptional parcels. Stretching just shy of a full acre from Kaneohe Bay Drive to the ocean, this property offers a gentle, park-like slope framed by breathtaking views of the Ko’olau Mountains and iconic Coconut Island, with no view of the Marine Corps Base to interrupt the natural beauty. A winding driveway leads through a canopy of mature trees, creating a private and enchanting arrival experience. The expansive grounds provide a canvas for a world-class custom residence, resort-style pool, guest accommodations, and outdoor entertaining spaces designed to capture Hawaii’s indoor-outdoor lifestyle. An existing home provides rental income or a place to reside while planning and permitting your dream estate. Just moments away, the Kaneohe Bay Yacht Club offers a vibrant waterfront lifestyle with sailing, tennis, pickleball, live music, family events, and the renowned Thursday evening regattas that can be enjoyed from the property itself. Equally appealing, the world-famous Kailua Beach is only a short drive away. Properties of this size, setting, and potential rarely become available.

44-375 Kaneohe Bay Drive, Kaneohe

Listing courtesy of eXp Realty.

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.

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