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$20,500,000
3 Beds 4 Baths 410482 MLS Fee Simple Tenure
Welcome to the quintessential Maui oceanfront estate, ideally situated on Keawakapu Beach—widely regarded as one of Maui’s most beautiful stretches of sand. This timeless Hawaiian residence embraces its unrivaled setting with approximately 2,500 square feet of covered outdoor living space, perfectly suited for beachfront lounging and entertaining. Designed with architectural integrity and island sensibility, the home features traditional Dickey rooflines topped with black glazed tiles imported from Japan. A electronic gate opens into a private, walled compound that includes the main residence, a detached two-bedroom guest cottage (Ohana), a two-car garage with workshop, and a beautifully landscaped courtyard with a pool and spa. The single level main home offers soaring 16 foot ceilings in the great room with a working fireplace serving as the centerpiece, complemented by an open-concept kitchen and expansive glass walls that frame breathtaking ocean views while preserving privacy. The main residence includes three bedrooms and four bathrooms, all designed with ease of access and comfort in mind. The detached two-bedroom, one-bath Ohana is finished to the same high standard, ideal for visiting family or guests. Set on 0.8 acres, the estate flows seamlessly from lush lawn to the beach, where a protective lava rock point cradles the property and collects soft white sand along this dramatic, crescent-shaped shoreline—one of the largest and most coveted on the island. A rare opportunity to own a true legacy property on Maui’s finest beachfront. **Disclosure** Some pictures have been Virtually Re-Staged and noted.

3146 S Kihei Rd, Kihei

Listing courtesy of Hawaii Life (W).

$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.

$19,750,000
7 Beds 9 Baths 406991 MLS Fee Simple Tenure
This magnificent oceanfront West Maui estate rests on approximately 1/2 acre of prime land in Kahana with over 250 feet of ocean frontage. Perfectly located between Kaanapali and Kapalua Resorts, this oceanfront property has no equal in the Hawaiian Islands. This nearly 10,000 square foot residence epitomizes Pacific Rim architecture. Glass pocket doors slide into rock walls bordering the spacious great room, which includes a grand living and dining area, as well as a fabulous open kitchen with separate enclosed butler's pantry. A floating mezzanine soars above the great room with a phenomenal sports bar and game tables. There are seven oceanfront suites, one being utilized as a media suite and one as a gym, each with a luxurious bath and most with a wet bar. Every suite is oceanfront with sweeping views of the neighboring island of Lanai and glimpses of Molokai. The large primary suite offers complete privacy and a fabulous outdoor lanai. The primary bathroom features an Italian custom two-person stone Jacuzzi tub, exquisite stonework, built-in wall speakers, and an expansive closet. An attached oceanfront one-bedroom Ohana can be utilized as a private office, for guests, or a caretaker. Extensive enhancements to the property include a new roof with 60KW photovoltaic solar system. Throughout the interior a selection of doors were replaced with new 10 ft. doors, freshly stained wood, new screens, and high-efficiency shades. A new Hydraulic elevator was installed, as well as new commercial-grade high efficiency air conditioning systems. Electronics have been significantly improved with a Control 4 System, a new Lutron system, top-of-the-line speakers throughout, as well as a state-of-the-art security camera system. A custom pool, complete with spa and waterfalls, is easily accessible from the great room. Moving outdoors, the oceanfront lanai and grilling area offer expansive coastal views. An outdoor landscape sound system has been integrated into the tropical gardens along with Tiki gas lamps and a fire pit from a local artist. The driveway was redesigned for convenience with the addition of a second entrance. Custom wood gates give the vehicular and pedestrian entrances a sophisticated natural appeal. Offered turnkey.

4809 Lower Honoapiilani Rd, Lahaina

Listing courtesy of Coldwell Banker Island Prop-KP.

$19,500,000
6 Beds 5 Baths 725480 MLS ['Fee Simple'] Tenure
Welcome to the breathtaking Hanalei Bay on the picturesque island of Kaua’i! This exceptional estate offers a truly unique and luxurious living experience. As you step onto the fully fenced and private grounds, you'll be greeted by two magnificent structures that define this remarkable property. The main residence, a stunning two-story masterpiece, commands awe-inspiring views of the ocean & mountains from its elevated perch. Boasting three bedrooms, an office, and generous living areas, this home exudes comfort and warmth. Unwind in the sumptuous soaking tub, a perfect retreat after a day of island adventures. Plus, with state-of-the-art solar hot water systems and photovoltaic panels, coupled with convenient switch panels, seamless transition from the grid to generators is effortlessly achieved. A highlight of this estate is its front-row seats to surf contests and the mesmerizing sight of paddlers gracefully gliding across the bay. The vibrant energy & beauty of the rare entire bay view are yours to savor right from your own doorstep. Convenience is paramount, with a back gate opening onto Pine Trees parking, adjacent to Waioli Beach Park & Pine Trees Beach. Easy access to the pristine sandy shores & verdant landscapes of the surrounding area. The second structure, positioned at the front of the property, features an elegant privacy gate opening onto the renowned Weke Rd. Delight in sweeping mountain views and meticulously manicured gardens from this vantage point. Offering two expansive stories & three additional bedrooms, and two outdoor showers, this structure ensures ample space to suit your lifestyle. For those cherished vehicles, rest assured, there's even a garage to shelter your prized automobile. A fusion of natural splendor, opulent living, & effortless access to the vibrant locale. Seize this rare opportunity to claim ownership of this extraordinary property and immerse yourself in the ultimate Hanalei Bay lifestyle.

5390 Weke Rd, PRINCEVILLE

Listing courtesy of Better Homes and Gardens Real Estate, Rainbow Island Properties.

$18,900,000
4 Beds 5 Baths 409020 MLS Fee Simple Tenure
Experience the best of South Maui living in this exclusive Makena Sunset residence, ideally located directly across from Maluaka Beach, Makena, Maui. Enter through a private gated entry to one of only four homes in this intimate and highly sought-after neighborhood. Enjoy the ultimate island lifestyle with the beach just steps away for snorkeling, swimming, and sunsets. This spacious home features 4 bedrooms and 4 full and 2 half baths, designed for comfortable indoor-outdoor living. The large open kitchen flows seamlessly into the main living area, perfect for entertaining family and friends. Outside, a private pool and spa create a relaxing retreat surrounded by the beauty and tranquility of Makena. Rarely available and exceptionally located, this property offers privacy, exclusivity, and effortless access to one of Maui’s most beloved beaches. This offering affords the new owner to apply for membership to Makena Golf and Beach Club. This offering is a standalone home within Makena Sunset, a Residential Condominium.

5417 Makena Rd Unit 2, Kihei

Listing courtesy of Discovery Makena Realty LLC.

$18,880,000
12 Beds 16 Baths 202520168 MLS FS - Fee Simple Tenure
Welcome to this exceptional Kailua beachfront estate. This gated resort-like retreat is situated on nearly an acre of land fronting one of the most beautiful beaches in the world. With over 14,000 sq ft of sophisticated living space, the main residence is a masterpiece of design featuring a luxurious, expansive primary suite with panoramic ocean views, and an additional 9 bedrooms-each boasting a private en-suite bathroom, a spacious gym/recreation room, 2 additional full bathrooms, and 2 powder rooms. Designed to entertain in style, this private tropical oasis is complete with an outdoor pavilion and full wet bar just steps away from a pristine pool, spa, and wading pool all set within beautifully manicured landscaping. A charming, detached 2-bedroom, 2-bathroom guest quarters and three-car garage further complement this magnificent property. Just beyond your backyard, a white sandy beach and the sparkling blue Pacific Ocean, ideal for swimming, ocean sports, or peaceful strolls. Embrace this once-in-a-lifetime opportunity to own this prime oceanfront property.

572C N Kalaheo Avenue, Kailua

Listing courtesy of REMAX Hawaii.

$17,950,000
4 Beds 5 Baths 404266 MLS Fee Simple Tenure
Nestled into a gated residential condominium community on Maui’s sun-drenched south shore, this 4-bedroom, 4.5-bath home provides over 4,300 sq.ft of interior space, beautifully renovated in 2024. This home offers stunning sunset views year-round. The updated kitchen has a substantial two-level island with Patagonia quartzite countertops and bar seating for six, with Leicht cabinetry, tile backsplash and amenities like a wine fridge and coolers. Two distinct living spaces and dining area open to the lanai, pool and spa creating an ideal setting for entertaining. In the winter months, enjoy whale watching with views of Molokini, Kahoolawe, Lanai, and Molokai. Enjoy snorkeling at one of the most premier snorkeling spots “Turtle Town”. On the ground floor there are two en suite bedrooms. Upstairs, the primary suite features a private ocean-view lanai, a wet bar and a bathroom with a soaking tub and large walk-in shower. The upper floor also contains the fourth bedroom and sitting area. Additional features include new 4-zone air conditioning, central vacuum system, recessed lighting, Jerusalem gold tile throughout, carpeted stairs and bedrooms, fresh paint inside and out, and wine cellar. New tile around the pool and spa. Just a short drive away you will find world-class dining, shopping and three exceptional golf courses.

4950 Makena Rd Unit 8, Kihei

Listing courtesy of Hawaii Life (W).

$17,500,000
5 Beds 7 Baths 730642 MLS ['Fee Simple'] Tenure
Set along a dramatic stretch of coastline within the prestigious Mauna Kea Resort, Hale 'O Ka La “House of the Sun” is not simply a home — it is a way of living that few places in the world can offer. Originally designed in 1992 and once featured in Architectural Digest, the property was thoughtfully reimagined in 2025 through an $8 million renovation led by Diane Bobek Designs, Taleah Smith Design, and Pono Hana Builders — preserving its architectural significance, while elevating every aspect of the experience. Arranged as a series of interconnected pavilions beneath a continuous roofline, the 5,358-square-foot Kauhale-style compound replaces traditional hallways with open-air breezeways that invite natural light, tropical gardens, and ocean air into everyday living. Every transition was intentionally designed to slow the pace. At the heart of the home, an open-air grand room anchors five bedrooms, five full baths, and two half baths — a layout where privacy and togetherness exist without compromise. Carefully preserved details — refinished dark wood accents, custom lighting crafted from salvaged copper roof fragments — speak to a renovation that understood what to keep as much as what to reimagine. Outside, the experience continues through layered tropical landscapes, sculpted pathways, and purposeful outdoor living areas designed to evoke satiation. A resort-style saltwater pool with waterslide and swim-up palapa bar serves as the estate's focal point, while a secluded waterfall grotto spa with integrated jacuzzi offers a more intimate escape among natural rockwork and shade. Surrounded by protected land, with no future development in front, and 355 acres preserved by the Queen Emma Land Trust to the north, the estate captures unobstructed Pacific and mountain views alongside rare, permanent privacy. A proven luxury short-term rental operation is in place and running. On the Kohala Coast, opportunities like this do not repeat themselves.

62-3916 Lanikeha Pl, KAMUELA

Listing courtesy of Hawaii Life.

$17,500,000
4 Beds 5 Baths 202609316 MLS FS - Fee Simple Tenure
Experience tranquil beachfront living in one of the most pristine areas along Kailua Beach, featuring stunning ocean views from the modern kitchen, spacious living room, and primary bedroom with a private oceanfront deck. Recent renovations include stylish baths that enhance the contemporary vibe. The custom kitchen flows into a welcoming dining area, ideal for gatherings and entertaining. A cozy cottage offers guest privacy, while ample parking and a three-car garage provide convenience. A dedicated office with courtyard access creates a peaceful workspace. Enjoy the lagoon pool and waterfall spa, with the beach just steps away for swimming, paddleboarding, or relaxing. Minutes from Kailua Beach Park, Mid-Pac Country Club, and Kailua Town, this home combines luxury and convenience. Your dream island lifestyle awaits!

200 S Kalaheo Avenue, Kailua

Listing courtesy of Coldwell Banker Realty.

$17,500,000
5 Beds 7 Baths 202609193 MLS FS - Fee Simple Tenure
This magnificent Diamond Head “Cove Area” beachfront masterpiece harmoniously fuses traditional Hawaiian architectural elements with an open modern lifestyle floorplan. Located on a quiet lane off Diamond Head Road, this home is truly a treasure to behold. The grand reception areas lead out to extensive wraparound lanai areas, a covered grill space, and a beachside seating area—perfect for enjoying sunsets and drinks while taking in the endless views of the Pacific Ocean. The upper level boasts a large primary ocean view bedroom, two additional en-suite bedrooms, elevator, gas generator and an unmatched office with ocean views that you’ll never want to leave. Refreshing pool, lush private landscaping, and unmatched location, style, comfort, and distinction define this Diamond Head gem.

218 Kaalawai Place, Honolulu

Listing courtesy of Coldwell Banker Realty.

$17,500,000
6 Beds 8 Baths 729749 MLS ['Fee Simple'] Tenure
Within the coveted enclave of the Mauna Lani Resort on the Kohala Coast, Hale Ohi‘a is regarded as one of Mauna Lani’s most architecturally significant private estates. Positioned along the 12th fairway where the ocean is seen, heard, and felt, the 0.66 acre property offers rare privacy and immediate coastal presence in a community where land of this scale is increasingly scarce. Built with more than 250 native Ohi‘a logs, now protected and no longer permitted for harvest, the residence represents craftsmanship that cannot be recreated under modern construction. The timbers rise through woven lauhala ceilings and expansive living spaces, anchoring the home in Hawai‘i’s landscape and tradition. Interiors reflect a refined approach to luxury with African mahogany cabinetry, onyx and tiger eye stone, Italian porcelain, kiawe hardwood floors, and custom Koa furnishings. Walls of glass open to the lanai where waterfalls, koi ponds, and a resort style pool and spa create seamless indoor outdoor living. The primary suite enjoys dual lanais and panoramic views across the Pacific toward Mauna Kea and Mauna Loa. Ownership includes access to the exclusive Mauna Lani Beach Club.

68-1028 Honokaope Pl, KAMUELA

Listing courtesy of Deep Blue HI.

$17,000,000
7 Beds 9 Baths 404095 MLS Fee Simple Tenure
Meticulously selected by the Islands' owner at the time for his personal home, The Lanai Estate was built to sit atop the most premier viewpoint and amongst the epitome of Hawaii's natural tropical beauty. This exclusive estate offers luxury living, modern elegance, and classic charm. Every architectural detail has been thoughtfully designed with craftsmanship and quality to integrate seamlessly with the surrounding landscape. Situated on a coveted private drive, this remarkable home serves as your harmonious doorway to the many enchanting experiences that the island of Lanai has to offer. Enjoy direct access to vibrant hiking trails, the equestrian community, a world-class golf course, hidden beaches, incredible dining such as Nobu and Nancy Silverton's Mozza, and the local Island club for easy access to two of the world-renowned Four Seasons amenities and wellness center. This property is more than just a home; it is a treasured legacy—a place where you can forge lasting memories against the backdrop of captivating beauty, ready to be passed down through generations. Embrace the opportunity to leave your mark on this paradise.

121 Kapihaa Pl, Lanai City

Listing courtesy of Deep Blue HI.

$16,995,000
5 Beds 7 Baths 202614590 MLS FS - Fee Simple Tenure
THIS IS NOT A.I.! This is one of Hawaii's rarest offerings, an estate that cannot be replicated & must be experienced to be believed! Prominently situated against the Ko'olau Mountains, this extraordinary 23+ acre legacy property offers an unparalleled opportunity to own a truly one-of-a-kind retreat. Hidden behind private gates & elevated above the coastline, this custom-designed smart home spans over 5,500 sq ft with 5 bedrooms, 5 full baths & 2 half baths. Designed for seamless indoor-outdoor living, expansive glass doors open to stunning lanais, a resort-style infinity-edge pool, sundeck & outdoor kitchen/BBQ pavilion - perfect for entertaining or quiet reflection. This self-sustaining haven features a spring-fed water system, 120-panel PV system & 6 Tesla Powerwalls. Additional highlights include Miele appliances, elevator, theater room with wet bar, central AC, fire sprinklers, 3-car garage with parking courtyard & more. The possibilities are endless across this expansive parcel of highly coveted land. A unicorn estate & once-in-a-generation opportunity...only ONE fortunate buyer will become the next steward of this magical treasure! *Sale Pending Final Public Report

47-958 Kamakoi Road, Kaneohe

Listing courtesy of Coldwell Banker Realty.

$16,950,000
5 Beds 6 Baths 410130 MLS Fee Simple Tenure
Perched on Maui’s coveted west side, this extraordinary 8-bedroom private estate offers a level of luxury, privacy, and craftsmanship rarely seen in Hawai'i. More than a home, this is a legacy estate, an irreplaceable Maui sanctuary designed for those who accept nothing less than extraordinary. Located in the coveted Plantation Estates at Kapalua community on the incredible 16th hole of the world-class Plantation Course, the property commands unmatched sweeping panoramic views across the Pailolo Channel framed by the stunning views of the outer islands of Lana'i and Moloka'i. Designed without compromise, the 2-acre estate encompasses more than 8,200 square feet across two separate residences, creating a private retreat unlike any other. Resort-caliber amenities include an infinity-edge pool and dual spas, private office, theater and fitness center. The 7,200 square foot 5-bedroom 5.5 bath main residence seamlessly blends indoor and outdoor living through expansive custom pocket sliding doors that open to reveal breathtaking ocean vistas and unforgettable sunsets. Rich natural materials, custom African Mahogany millwork, exotic stone, and world-class finishes define every space, from the chef’s kitchen and grand great room to the spectacular primary suite. A fully appointed three-bedroom guest cottage with its own pool, fire-pit and Palapa set over a koi pond provides exceptional accommodations for family, guests, or staff while maintaining complete privacy. Aside from world-class golf, the Kapalua resort offer the utmost in amenities including award-winning spa, tennis and pickleball, exquisite dining options and some of the finest beaches: Fleming Beach, Oneloa Bay and Kapalua Bay, which was rated as the Best Beach in America by Conde Nast Travel Magazine.

706 Mokuleia Pl Unit 6, Lahaina

Listing courtesy of Keller Williams Realty Maui-L.

$16,500,000
6 Beds 8 Baths 202611158 MLS FS - Fee Simple Tenure
Sophisticated, Modern, Unlimited Ocean Views...Designed to relish in the beauty of magnificent indoor spaces coupled w/ a seamless integration to expansive outdoor living this stunning ultra-luxury residence designed by renowned HI Architect Jim McPeak offers uninterrupted Diamond HD, ocean & coastline views, and the best direct sunset vistas on the island. Situated on Oahu’s Southeastern shoreline overlooking Maunalua Bay this breathtaking 6-BD, 7.5-BA residence offers exceptional appointments & a true private luxury resort experience. The Great Rm welcomes you w/its awe-inspiring panoramic landscapes, soaring custom wood inlaid ceilings, pocketing walls of glass & assortment of natural stone textures. The chef’s kitchen w/prof appliances provides a wonderful connection to both the dining alcove & lounge areas. The Primary Suite w/ secluded sitting nook, seaside lanai and dream spa like bath is stunning, Each BD suite provides a sensory experience & soothing sounds of the ocean waves. This modern-day masterpiece is complete w/ a gated, dual access driveway providing ample onsite parking + garage parking for 3-cars. For those in search of a stunning island villa, welcome home.

176 Hanapepe Loop, Honolulu

Listing courtesy of Coldwell Banker Realty.

$16,500,000
5 Beds 6 Baths 731721 MLS ['Fee Simple'] Tenure
Embrace Kauai oceanfront living at its finest within the premier 10-lot enclave of Makahuena Estates. This newly constructed 1-acre and five-bedroom shoreline estate defines the epitome of island living. The two-story coastal contemporary residence rests on a bluff along the Poipu Beach coastline, offering uninterrupted views of the beach, ocean, sunrise, and sunset. With an open floor plan, clean lines, high wooden beam ceilings, floor-to-ceiling windows, and expansive glass doors that open to lanai areas, the home's design intrigues. Inside, warm wood tones and serene thoughtfully layered textures create a natural harmony with the awe-inspiring coastal environment. Entertaining is easily accommodated by way of the fully equipped kitchen, butler’s pantry and accompanying covered barbeque lanai. Serve up anything from an organically sourced Kauai meal for 2 people to an elaborate Pacific Rim celebratory feast for the crowd knowing that you have the space, storage and equipment to handle everything. To cap it off, serene and graciously proportioned bedroom suites await, each featuring elegant en-suite baths with lanai spaces that convey a barefoot elegance. And, before retiring, take a dip in the oceanfront infinity pool and spa – a perfect day in paradise. HOME FEATURES Land Area: 1.001 Acres Design: 2-Story Coastal Contemporary Residence Square Footage: Interior SF: 4,080 + Lanai SF: 2,472 + Garage: 870 Bedrooms & Baths: 5 Bed | 5.5 Baths Use: Long Term or Vacation Rental Use Neighborhood Amenities: Private Clubhouse - fitness, sauna, indoor & outdoor showers, lounge and putting green Entry: Gated Etc: Coastal Path, Lighthouse, Coastline

2177 Maka Pl, KOLOA

Listing courtesy of COMPASS.

$16,000,000
4 Beds 5 Baths 403334 MLS Fee Simple Tenure
BRAND NEW HOME NEVER OCCUPIED MOVE IN READY. An exceptional residence where uncompromising attention to detail and a harmonious fusion of comfort and nature creates a testament to unparalleled quality and sophistication. Where every day is an opportunity to savor the beauty and tranquility that defines the essence of Hawaii. Located within the exclusive Mahana Estates, a gated enclave in the world-renowned Kapalua Resort on Maui. A flagship smart home with the latest in Lutron, Elan and Tesla home technology and energy with incomparable conveniences promises a care free lifestyle. Miele appliances in a modern kitchen design, four bedrooms and four and one-half baths, a three-car garage and extensive storage cater to the practical needs of its residents, whether it be a primary home or an exquisite vacation retreat. Boasting views that include the beautful Kapalua Bay, the majestic West Maui mountains, and the island of Molokai. Floor-to-ceiling windows bathe the oversized rooms with natural sunlight, while expansive ceilings invite gentle ocean breezes, creating an atmosphere of serenity and openness. An infinity pool, spa and an outdoor fireplace sets the mood for intimate gatherings. While an outdoor kitchen provides a space for culinary delights with the backdrop of the Pacific Ocean. Whether entertaining guests or unwinding in solitude, the outdoor areas offer a perfect balance of comfort and style.

210 Naio Pl, Lahaina

Listing courtesy of Island Sotheby's International Realty(L).

$15,950,000
5 Beds 7 Baths 202615041 MLS FS - Fee Simple Tenure
Set on one of Hawaii Loa Ridge's most coveted lots, this five bedroom, six and one half bath residence delivers uninterrupted views of Diamond Head, the Pacific Ocean, and Honolulu's coastline from nearly every room, with complete privacy from neighbors and the street. Award-winning architect Jeff Long paired steel-and-concrete construction with interiors built by artisans whose past work spans ultra-luxury yachts and the ateliers of Chanel, Cartier, and Hermes. Book-matched travertine and marble carry through the home, alongside Spinneybeck and Holly Hunt Italian leather walls and Molteni closet systems. A pneumatic glass elevator connects the levels, and a private theater and wine cellar round out the entertaining spaces. The Pininfarina-designed kitchen centers on a Taj Mahal quartzite island, Snaidero cabinetry, dual Sub-Zero refrigerators, and Gaggenau appliances. Outside, a saltwater infinity pool and spa sit within a landscaped lanai framed by the same sweeping views. German-engineered shutters, a full security system, and 24-hour gated access make this a genuine lock-and-go estate.

360 Puuikena Drive, Honolulu

Listing courtesy of Compass.

$15,750,000
5 Beds 6 Baths 731293 MLS ['Fee Simple'] Tenure
Exceptional ocean, sunset, and Keʻolu Golf Course views define this custom residence in Hualālai Resort's Hokuloa Estates. Designed to embrace Hawaiʻi's renowned indoor-outdoor lifestyle, the expansive great room opens through handcrafted pocket and louvered doors to an enlarged lanai and exceptional outdoor living spaces. A private gated courtyard entry welcomes you to this thoughtfully designed home featuring four bedrooms, an office with ensuite bath currently utilized as a fifth bedroom, and a spacious media room. Interior finishes include travertine flooring, granite countertops, and numerous quality upgrades throughout. Outdoor amenities include an infinity-edge pool and spa, expansive lawn, gas tiki torches, fire bowls, and a fully equipped outdoor kitchen with barbecue, refrigerator, sink, generous counter space, and bar seating—ideal for entertaining while enjoying the stunning ocean and golf course views. Beautifully maintained tropical landscaping enhances the property's appeal, while recent improvements include updated HVAC systems, refinished exterior trim, and an updated roof. An oversized garage currently used for four golf carts and one vehicle. Ideally located on one of Hualālai Resort's premier view streets, this exceptional home enjoys a coveted lower resort location and is just a short golf cart ride from the Resort's world-class amenities, including championship golf, beaches, dining, spa facilities, fitness center, and club services.

72-118 Hokuloa St, KAILUA KONA

Listing courtesy of COMPASS.

$15,500,000
3 Beds 3 Baths 406314 MLS Fee Simple Tenure
Hawaiiana meets contemporary design with this exceptional estate on the pristine shores of Keawakapu Beach. The property has been approved for a renovation expanding the home to a 5-bedroom, 5-bath home. Construction to commence early 2026. Beyond the gated entrance lies a world of relaxation and rejuvenation, where quality adjoins an unrivaled location. Upon entering the property, you're surrounded by lush tropical landscaping and the soothing sound of waves crashing against the shoreline. The grand entrance opens into a sprawling foyer where warm tones and gentle breezes are abundant. The open and airy interior seamlessly blend indoor and outdoor living spaces to capitalize on Maui's year-round sunshine and uninterrupted ocean views. The first level features an expansive kitchen with butlers pantry, sprawling great room, and the primary guest room with en suite. Outside the multiple sets of dramatic pocket sliders, is a large courtyard area and pool, just steps away from the sand. Below the pool area is an additional large yard, perfect for entertaining and an outdoor shower for rising off after a day at the beach. Retreat upstairs to the massive primary suite, where there are panoramic views of the Pacific Ocean and Keawakapu Beach. Complete with a luxurious en suite bathroom and private balcony. Additional highlights of this exceptional property include a spacious 1,000 square foot garage, providing ample space for your vehicles, water toys, and outdoor gear. Perhaps the best feature of this home are the unparalleled views of three neighboring islands – Molokini, Kaho'olawe, and Lana'i – from just about every room in the house. Experience the Maui lifestyle in this exquisite beachfront retreat, where every day feels like a vacation and paradise is truly found at home.

3002 S Kihei Rd, Kihei

Listing courtesy of Hawaii Life (W).

$15,000,000
3 Beds 4 Baths 410537 MLS Fee Simple Tenure
Experience the relaxed beauty of the Hawaiian lifestyle in this special West Maui oceanfront estate. Set on two acres of lush, naturally landscaped grounds within a small gated oceanfront community, this tropical paradise offers a rare combination of space, comfort, privacy, and authentic indoor-outdoor island living. The 3-bedroom, 3.5-bath main home is warm, open, and designed to embrace Maui’s natural surroundings. Cathedral ceilings, polished concrete floors, and open living spaces invite the ocean breeze indoors. The gourmet kitchen features high-end appliances and flows naturally to the covered lanai, creating an inviting setting for morning coffee, sunset dinners, & gatherings with family and friends. Each bedroom offers its own en-suite bathroom and private enclosed outdoor shower—a quintessential Hawaiian touch that brings you closer to nature. Outside, the resort-style pool with cascading waterfall creates a peaceful retreat, while the Pacific Ocean provides a beautiful backdrop. A separate 2-bedroom, 1-bath ohana offers comfortable space for visiting family & friends. Features include a gated entry, photovoltaic solar system with Tesla battery storage, 3-car garage, additional storage for kayaks, surfboards, and other ocean gear. A true Maui home where ocean, nature, family, and the laid-back Hawaiian lifestyle come together.

49 Kuahulu Pl Unit Lot 4-C, Lahaina

Listing courtesy of Coldwell Banker Island Prop-KP.

$15,000,000
2 Beds 2 Baths 402660 MLS Fee Simple Tenure
This 54+ acre estate is one of a kind---a secluded and private retreat. With careful attention paid to every detail, it provides a rare opportunity for those seeking privacy, seclusion, and a peaceful lifestyle in one of the most desirable areas on Maui. The main house is situated on a high promontory, with commanding ocean views that extend across Alenuihaha Channel to the island of Hawaii (the “Big Island”). The finely detailed home is open and spacious, featuring a vaulted ceiling, a wrap-around deck/lanai, and, on the view side of the living area, a floor to ceiling glass wall. The property is comprised of two adjoining parcels totaling 54+ acres. The main parcel is bordered on one side by a seasonal stream and on the other side by a running stream featuring several waterfalls and pools. In addition to the two bedroom/two bath main residence this immaculately maintained property includes a massive private well and water system, a state of the art photo-voltaic system with battery and generator back-up, a six bay garage with an attached office, a four bay agricultural workshop, and separate ocean view 2 bedroom living quarters. This distinctive estate incorporates all of the features that define island living. Offered fully furnished.

40723 Hana Hwy, Hana

Listing courtesy of Island Sotheby's International Realty(M).

$14,900,000
6 Beds 7 Baths 725879 MLS ['Fee Simple'] Tenure
Artevilla is a luxury, two story, six bedroom, ocean view residence situated just above the beach at Mauna Lani Resort. Typically Hawaiian in style, the house is designed to blend seamlessly with its lush tropical and romantic surroundings and provides the perfect environment for an ultimate and memorable Hawaiian vacation experience. Situated in one of the most exclusive gated communities in the state, this villa simultaneously offers the peacefulness of a protected environment, the charm of a fantastic ocean view, gorgeous sunsets and the exclusive services of high-end Resort. Walk in three minutes to your private beach club and experience the convenience of nearby golf, tennis, spa, shops, restaurants and more. Artevilla was conceived to be the perfect combination between the art of Hawaiian well-being and contemporary style. Environmentally current, the home runs efficiently on solar energy. This spectacular and unique property offers a spacious great room with a vaulted, twenty foot ceiling surrounded by large sliding glass pocket doors. Listing is sold unfurnished. Please consider Title Guaranty Escrow, Rae-Ann Ontiveros

68-1056 Pauoa Way, KAMUELA

Listing courtesy of Anne Rediske REALTOR.

$14,750,000
6 Beds 7 Baths 730105 MLS ['Fee Simple'] Tenure
All year round sunset views! Hapuna Estates at Mauna Kea Resort Lot 12 offers expansive Pacific Ocean views, Hualalai view to the south, Maui to the north and the 8th green and fairway views of the Hapuna Arnold Palmer Golf Course! Designed and developed by the trusted team of Paul Bleck and Brown Development, this estate residence features 6BR 6.5BATH, pool & spa, spacious great room and a gourmet kitchen, totaling approximately 5,957 sf of livable area on 1.33 acres in the prestigious Hapuna Estates subdivision inside of the Hapuna Resort gate. The home is offered furnished, perfect for both personal enjoyment and as a short-term vacation rental. With a Club at Mauna Kea membership, you will gain access to the resort’s world-class amenities in both Mauna Kea Beach Hotel and Westin Hapuna Beach, including two golf courses, tennis courts, pristine beaches, fitness centers, gourmet restaurants, and more. Enjoy the convenience of charging privileges and take advantage of discounts on various services. Mauna Kea Beach Hotel is currently going under $180-million renovation. Additionally, the Hapuna Estates Association membership grants you access to the private amenity center, featuring a half-Olympic-sized pool, a 130-foot water slide, BBQ areas, a gym, and an orchard and garden. Some of the features include, but not limited to: * All year round sunset views * Pool & spa overlooking a golf hole and the Pacific Ocean and mountain views * Taj Majal Quartzite for the kitchen island, vanity and backsplashes * Luxury Wolf, Subzero and Bosch appliances in the kitchen * Wolf Outdoor BBQ Grill * Under-counter refrigerator and a sink in the guest room for your guest's convenience * Maytag front-load washer & dryer * Beautiful built-in mahogany cabinets * 3 outdoor showers * STVR allowed and more... The home will be completed in Summer 2026!

62-4402 Amaui Nani Pl, KAMUELA

Listing courtesy of BD Properties Hawaii LLC.

$14,750,000
4 Beds 5 Baths 405257 MLS Fee Simple Tenure
Step into a world of refined elegance and beachfront luxury in Maluhia at Wailea—a sanctuary within Wailea’s most exclusive beachfront enclave. Tucked behind the gates of this community of just 14 bespoke estates, this 4,800+ sq. ft. home is a fusion of contemporary sophistication and the raw, natural beauty of Hawaii. There are four exquisite bedrooms, including a lavish primary suite on the second level and additional primary suite on the first level, perfect for multi-generational living or hosting in style. The four full bathrooms can be viewed as curated sanctuaries, adorned with spa-inspired finishes and an ambiance of serenity. The home is being sold furnished and is move-in ready. Beyond its high quality interiors, the home unveils an expansive outdoor haven, with a resort-style pool, private spa retreat, and a lounge area that invites you to indulge in the backdrop of Maui’s legendary sunsets. With direct access to the beach, the crystal-clear waters of Wailea’s shoreline are just steps away, offering a connection to the island’s natural splendor. As a resident of Maluhia at Wailea, you’ll enjoy the private Maluhia Beach Club with a resident manager who lives at the beach club, an oceanfront escape featuring a catering kitchen, wet bar, and private storage for your beach and water activities. Located just moments from golf courses, five-star dining, and high-end designer boutiques and shops, this property embodies a balance of tranquility and quality.

19 Malukai Ln Unit 4, Kihei

Listing courtesy of Hawaii Life (W).

$14,500,000
5 Beds 6 Baths 202615821 MLS FS - Fee Simple Tenure
Exceptional Portlock Estate. This oasis is along one of Oahu's most prestigious beaches. Iconic Diamond Head & Sunset Views. Rare Adjacent Vacant Lot. The property features a gated entry, leading to a fabulous private retreat. Inside, you'll find a spacious, flowing floor plan that extends to a beautifully tropical landscaped yard. The home includes a spacious primary bath and a large covered entry. The expansive yard is complete with a pool, waterfall, gas BBQ, and a pavilion, perfect for entertaining. This offering includes 2 separate parcels. A 14,491 sq ft lot with a 2 story 5 bedroom, 5.5 bath home (TMK 1-3-9-3-8) and an adjacent 13,500 sq ft vacant lot (TMK 1-3-9-3-11). To be sold "As Is".

Honolulu

Listing courtesy of Zen Properties Incorporated.

$14,250,000
6 Beds 8 Baths 202604666 MLS FS - Fee Simple Tenure
Spectacular beachfront estate ..two separate parcels seamlessly combined.Stroll through immaculately landscaped grounds with soothing waterfalls throughout and a separate guest studio.Fully walled for privacy.Step into this architectural masterpiece designed by well known architect Jeff Long with grand foyer directly looking out to breathtaking beach, ocean, and Diamond Head Views!! Three primary suite-sized bedrooms..one suite on the main level...all enjoying Diamond Head and ocean views. Two other primary suites on the upper level with "Romeo and Juliet" balconies looking down to the foyer.Open floor plan with soaring ceilings ... finished with the finest materials..hardwood floors,wood trim in bedroom ceilings,etched glass touches,floor to ceiling sliding glass doors..close to island themed restaurants by the marina, shopping, Hanauma Bay, Sandy Beach..Your own Private Hawaiian Paradise..Simply STUNNING!! Both TMK's are being sold together for a total purchase price of $14,250,000. This spectacular dream retreat is also a Celebrity Home ... having been featured in multiple episodes of Hawaii Five-O. Your chance to own a piece of Hollywood and paradise all in one !!

255 & 257 Portlock Road, Honolulu

Listing courtesy of Coldwell Banker Realty.

$14,200,000
4 Beds 6 Baths 726476 MLS ['Fee Simple'] Tenure
A Coastal Masterpiece of Timeless Elegance Commanding a premier view homesite, this estate within Kukui'ula captures the essence of Kauai’s historic charm fused with modern sophistication. From lush, intimate gardens to the endless ocean horizon and glowing sunsets, every perspective is a work of art. Inside, craftsmanship reigns supreme—Ipe hardwood floors, soaring coffered ceilings, custom millwork, and natural stone accents frame sweeping 180-degree ocean, coastal, and mountain views. The chef’s kitchen is a culinary sanctuary, featuring honed marble countertops, bespoke cabinetry, and elite appliances by Sub-Zero, Wolf, Fisher & Paykel, and Thermador. A butler’s pantry and custom Koa banquette seating complete this gourmet haven designed for both artistry and gathering. The primary suite wing offers a serene retreat with an ocean-view lanai, private outdoor shower garden, and dual private wardrobes. On the opposite wing, a secondary suite welcomes guests with panoramic views, custom built-ins, and an alfresco shower experience. Upstairs, discover a media and game room where vistas stretch “as far as the eye can see,” complemented by a cozy twin room with built-ins. For additional flexibility—whether for an art studio, office, or home gym—the detached guest house provides a 4th sleeping room, bath, living area, wet bar, and lanai. Outdoors, indulge in an infinity-edge pool, spa, and firepit, serene courtyard with koi pond, terraced gardens, and fruit trees—all set against commanding ocean vistas. For shaded relaxation, the luxuriously appointed lanai room with wet bar overlooks it all. This is more than a home—it’s a statement of elegance, privacy, and coastal living at its finest. View the Video (copy/paste into browser): https://player.vimeo.com/video/1146713224

5741 Ka Hookui Pl, KOLOA

Listing courtesy of COMPASS.

$14,000,000
4 Beds 4 Baths 410153 MLS Fee Simple Tenure
Set on beautifully curated grounds in Spreckelsville on Maui's North Shore, this extraordinary oceanfront estate embodies the timeless character of Old Hawaii, while offering a lifestyle centered around ocean, wellness, and understated luxury. Framed by sweeping views of the Pacific and peaceful bays stretching in both directions, the gated estate occupies one of the most breathtaking settings in Hawaii. A private pathway provides effortless access to a pristine white sandy beach lies just moments away. The compound features two tastefully renovated residences that honor their original plantation-era architecture while incorporating modern comforts and craftsmanship. The main home's four en suite bedrooms, inviting gathering spaces, and beautifully appointed chef's kitchen were designed to bring family and friends together, creating an atmosphere that is both sophisticated and welcoming. There's also a detached ohana perfect for guests or a caretaker. Life here revolves around connection—to nature, community, and the sea. World-class wingfoiling, kitesurfing, surfing, paddling, cycling, and beach walks await just beyond the property. The nearby Maui Country Club with golf, tennis and pickelball have further elevated Spreckelsville as one of Hawaii's most desirable coastal communities for those who embrace an active and healthy lifestyle.

477 Laulea Pl, Paia

Listing courtesy of Hawaii Life (W).

$13,999,000
409243 MLS Fee Simple Tenure
Exceptional 58-acre agricultural estate comprised of eight separate TMKs, featuring a unique combination of high-quality improvements, established income, and long-term flexibility. The property includes four substantial ag buildings, two fully automated commercial greenhouses, and extensive infrastructure throughout. Improvements include a 1,300 sq ft Ag Office/Studio (2023) with slab-on-grade construction, 2x6 framing, Marvin windows, hardwood floors, split-pitch roof, R-19/R-30 insulation, Lutron automated lighting and shades, and Sonos audio. A 4,200 sq ft Ag Shop/Storage/Office offers 12’ walls, a 12/12 standing-seam metal roof, loft with hardwood flooring, and a Solark/Discovery off-grid PV system with 74kW storage. A 5,000 sq ft bolt-together Curvco galvanized corrugated metal ag shop with (2) 11' x 11' roll-up doors provides additional covered workspace and storage. A 2,400 sq ft Ag Warehouse with 12’ walls and standing-seam metal roof is also supported by the same off-grid solar system. Two 3,600 sq ft Agri-Tech Solar-Lite greenhouses, both fully automated and have supported a proven agricultural operation. Existing leases generate substantial income. Significant site work has been completed, including approximately 4,000 linear feet of 12-foot-wide asphalt drive providing secondary ingress/egress, an additional 800 linear feet of asphalt and concrete, four 12’ x 100’ concrete swales, and approximately 8,000 linear feet of perimeter game fencing. Roughly 40 acres have been cleared of old-growth wattle. This is a solid opportunity to acquire a large-scale, income-producing agricultural property with new infrastructure, multiple revenue streams, and long-term value.

7700 Kula Hwy, Kula

Listing courtesy of Hawaii Life (W).

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.