Jude Augustine Featured Properties

8 Beds ⋅ 8 Baths ⋅ 409860 MLS ⋅ Fee Simple Tenure

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

4640 & 4650 Makena Rd, Kihei

Listing courtesy of Hawaii Life (W).

$35,000,000

2 Beds ⋅ 2 Baths ⋅ 408193 MLS ⋅ Fee Simple Tenure

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

5670 Hana Hwy, Hana

Listing courtesy of Hawaii Life (PR).

$29,900,000

5 Beds ⋅ 6 Baths ⋅ 407766 MLS ⋅ Fee Simple Tenure

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

5050 Makena Rd, Kihei

Listing courtesy of Discovery Makena Realty LLC.

$26,500,000

6 Beds ⋅ 6 Baths ⋅ 409734 MLS ⋅ Fee Simple Tenure

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

7505 Makena Rd, Kihei

Listing courtesy of Compass-W.

$24,500,000

4 Beds ⋅ 6 Baths ⋅ 408751 MLS ⋅ Fee Simple Tenure

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

3060 S Kihei Rd, Kihei

Listing courtesy of Coldwell Banker Island Prop(S).

$24,500,000

5 Beds ⋅ 6 Baths ⋅ 408059 MLS ⋅ Fee Simple Tenure

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

3254 S Kihei Rd, Kihei

Listing courtesy of Hawaii Life (W).

$23,000,000

4 Beds ⋅ 5 Baths ⋅ 402062 MLS ⋅ Fee Simple Tenure

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

7595 Makena Rd, Kihei

Listing courtesy of Compass-W.

$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.

$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.

$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).

$17,000,000

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.

$16,950,000

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.

$16,800,000

4 Beds ⋅ 6 Baths ⋅ 407851 MLS ⋅ Fee Simple Tenure

WHERE THE SEA WHISPERS . . A Contemporary Expression of Timeless Oceanfront Living. Happy to accept backup Offers!! Pending in escrow and also Happy to show!! Closer to the ocean than almost any home on Maui -impossible to duplicate under today’s building regulations - direct-oceanfront estate delivers a level of proximity, craftsmanship, and design that defines rare. Set just 25' from the Pacific - 75' linear frontage - elevated 12' feet - this masterpiece captures panoramic year-round sunsets. As the evening unfolds, tap your mobile phone and watch your tiki torches glow while you relax at the ocean’s edge - a signature lifestyle moment. The state-of-the-art Lutron smart home controls four ocean-inspired ensuite bedrooms - five-and-one-half baths - glass-roof pool lounge with jacuzzi & waterfall - five-zoned a/c - 84 owned PV solar panels - two-car garage a/c - separate two-bedroom guest house. Walled and gated for complete privacy, security and serenity. Very rare oceanfront offering - an architectural achievement and a lifestyle unmatched. Completed in 2013 with wood-and-steel beam construction engineered for up to 150+mph wind loads - Custom IB roofing system 25 year warranty - fully permitted sea wall - exceptional materials and architectural precision throughout. Hand-selected marble, granite, and sandstone imported from Greece - Automatic 9’6” Fleetwood sliding glass doors & screens open at the touch of a button - or from your smartphone. Sculptural Sapele wood ceilings soar 10' to 20' illuminated by modern 3” recessed square LED lighting. The breathtaking custom blonde-walnut and stainless-steel floating staircase serves as the home’s contemporary centerpiece. The dramatic 12-foot floating double-glass "wave" kitchen bar - artistically lit for evening ambiance - the floating gold-inlaid automatic book matched cabinetry - the additional butler’s pantry - the in & out upstairs glass showers - stand as some of the home’s most memorable design features. As one of South Maui’s hidden oceanfront gems - where wellness and community combine to become part of your daily living - where morning walks, sunset jogs, oceanfront cycling, and easy access to ocean swimming are part of everyday life - a charming, low-traffic neighborhood where residents enjoy an authentic, active, and family-friendly island lifestyle with a nearby kid-friendly park. Looking for Buyers with the commitment to love, respect, and maintain this exquisite property.

1750 Halama St, Kihei

Listing courtesy of Compass-W.

$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).

$15,500,000

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

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).

$14,750,000

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).

$14,400,000

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).

$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

4 Beds ⋅ 5 Baths ⋅ 408866 MLS ⋅ Fee Simple Tenure

Perched high above the coastline within the private gated enclave of Honolua Ridge, this extraordinary single-level estate captures a vantage point so rare it feels as though the Pacific, Moloka‘i, and the Pailolo Channel were reserved exclusively for you. Set on more than six pristine acres in Kapalua Resort, the panoramic views are expansive, intimate, and ever-changing — a daily masterpiece of blue water, outer island silhouettes, and golden sunsets. This is one of those homes where you pause… and just take it all in. Designed and constructed as the personal residence of one of West Maui’s most respected builders, the home is a statement of intentional design and uncompromising craftsmanship. Every finish, every material, every line was curated with longevity, beauty, and a deep respect for the setting. The grand great room opens seamlessly to an expansive lanai where a resort-style pool and spa are framed by flickering tiki torches, creating an atmosphere that transitions effortlessly from sun-drenched afternoons to refined evenings under the stars. It’s easy to imagine quiet mornings with coffee overlooking Moloka‘i, or gathering with friends as the sky melts into color over the blue expanse. Throughout the residence, extraordinary details abound. Modern infrastructure matches the timeless aesthetic, including , dual laundry rooms, a double septic grid system, a dedicated media room with full surround sound, custom primary closet and a three-car garage with oversized bays. Eagle concrete roof tiles and genuine stucco construction further reflect the enduring quality of this estate. The lower portion of the acreage offers a prime homesite for a future ohana residence — ideal for extended family or guests seeking privacy within the estate’s expansive grounds. A rare spring-fed pond adds yet another layer of serenity to this already remarkable property. Opportunities like this are few and far between on Maui — especially in Kapalua’s most private ridge setting. This is more than a home. It’s a legacy estate where craftsmanship, space, and sweeping ocean views converge in unforgettable fashion.

222 Ke'oawa St, Lahaina

Listing courtesy of Hawaii Life (W).

$12,900,000

5 Beds ⋅ 8 Baths ⋅ 409428 MLS ⋅ Fee Simple Tenure

Nestled withing the prestigious enclave to Kapalua Place, this extraordinary oceanview estate on over 1 landscaped acre offers an unparalleled blend of luxury, privacy, and island elegance. Encompassing over 10,000 square feet of living space, the magnificent five bedroom, 7.5 bath residence is designed to capture the essence of refined Hawaiian living. Thoughtfully crafted with an expansive open floor plan, the home flows seamlessly from grand interior living spaces to breathtaking outdoor spaces perfect for effortless entertaining and relaxed island living. Walls of glass frame panoramic ocean vistas while inviting natural light and gentle trade winds throughout the residence. The open chef's kitchen with gorgeous granite countertops anchors the main living area and opens to generous living and dining areas for hosting both intimate dinners and large celebrations. Each of the 5 bedroom suites offers exceptional comfort and privacy creating a serene retreat for family and guests alike. Complete with an elevator. The resort style outdoor living spaces create a tropical sanctuary designed for both relaxation and entertaining. At the heart of the grounds is a spectacular swimming pool accented by a cascading waterfall evoking the ambiance of a five star luxury living in the Kapalua resort. There is a separate private spa. Set within Maui's most coveted enclaves, this remarkable property provides both exclusivity and proximity to the world-class amenities of Kapalua, including championship golf, pristine beaches, fine dining, and luxury resort experiences. A rare offering where timeless architecture, breathtaking ocean views, famous sunsets and the west maui mountains frame the views and the spirit of aloha come together in perfect harmony. Private gated enterance to the white sand beach at Oneloa Bay with views up the coastline to Honolua Bay.

8 Kapalua Pl, Lahaina

Listing courtesy of Keller Williams Realty Maui-L.

$12,900,000

8 Beds ⋅ 13 Baths ⋅ 408480 MLS ⋅ Fee Simple Tenure

Located in gorgeous Napili, Maui, 5385 Lower Honoapi'ilani Road, also known as the Napili Beach House, is a uniquely spacious Maui home boasting stunning views of Napili Bay, the enchanting island of Moloka'i, and incredible features throughout. Amenities include a gated entrance, a heated rooftop ocean-view swimming pool with spa, an outdoor rooftop kitchen with a built-in barbecue, an elevator, two dining areas, two Great Rooms, two dens, and twelve Smart TVs. The home's expansive rooftop deck features a magnificent swimming pool and jetted spa, surrounded by panoramic ocean views and a majestic mountain backdrop. Imagine taking a dip in the pool or luxuriating in the jetted spa as you soak in the breathtaking sunset every evening. During winter, you can watch majestic humpback whales frolicking just offshore from the comfort of your home's private perch! The rooftop also includes an outdoor kitchen, barbecue, dishwasher, and refrigerator, allowing you to prepare meals in a stunning setting. You can enjoy breathtaking views from the second floor, which features two magnificent Great Rooms and four exquisite bedrooms, transforming it into the vibrant heart of this extraordinary home. The second floor is accessible via a private elevator or two staircases, making the home mobility-friendly. On one side, you'll discover a culinary haven with a gourmet kitchen, dining area, and a spacious Great Room. On the other side, indulge in the ultimate entertainment experience at the sleek wet bar, accompanied by a wine fridge, a second dining area, and an equally impressive second Great Room! Large sliding glass doors seamlessly connect two distinct lanai areas. The gourmet kitchen is well-appointed, with everything a home chef may need. There is a 5-burner range, double refrigerator, dishwasher, and microwave. A full-size freezer and a separate commercial ice maker are just off the kitchen. Eight bedrooms provide ample space for family and friends. All bedrooms have en-suite baths and are lavishly outfitted with California King beds. Each first-floor bedroom opens onto a quiet lanai in the backyard, sheltered from street view, while the four second-floor bedrooms offer stunning ocean views. The first floor also features two offices and two private dens equipped with large Smart TVs in a media-room setting. Central air conditioning with individual climate controls and ceiling fans ensures personalized comfort in every room. You are also within walking distance of gorgeous Napili Bay and a short drive from award-winning Kapalua Bay Beach and the world-class PGA Plantation Course. This unique home offers a rare opportunity for someone seeking a large Maui residence close to the ocean, services, and entertainment. The property must be seen!

5385 Lower Honoapi'ilani Rd, Lahaina

Listing courtesy of Welcome Hawaii Properties.

$12,900,000

4 Beds ⋅ 4 Baths ⋅ 406606 MLS ⋅ Fee Simple Tenure

Perched on a sweeping green slope with panoramic ocean and mountain views, this award-winning Haiku retreat blends modern architecture with the serene elegance of a high-end sanctuary. Designed by renowned firm SEE Architecture, the home draws inspiration from iconic museums like the Getty and Venice Guggenheim, mid-century modern design, and the quiet refinement of luxury retreat spaces. Behind a minimalist facade, the experience unfolds—floor-to-ceiling glass reveals unobstructed vistas, blurring the line between indoors and out. Natural materials—including vein-cut silver travertine, western red cedar, and walnut crafted by local artisans—anchor the home to its surroundings. The structure itself is a precision steel BONE system, designed for longevity and environmental harmony. Inside, the interiors are curated with intention: Florim Italian porcelain tile throughout, custom millwork by Henrybuilt in the kitchen, baths, and beyond, handmade Heath Ceramics tile details, bronzed Honduran mahogany pivot door entry, Forbes & Lorax light switches, Phillip Jeffries woven wall coverings, and Waterworks fixtures and finishes. The open-plan layout flows effortlessly from artful entry to the main living spaces, with every room oriented toward the lush, private acreage and distant blue horizon. Beyond the glass, the landscape includes sculptural elements like Chinese scholar’s rocks, a sleek modern swimming pool, and rolling pastures where horses roam. A separate guest cottage provides additional space for visitors, work, or creative pursuits, all while maintaining the retreat’s sense of privacy. The arrival experience is equally compelling—lush, mature landscaping lines the private drive, a verdant gateway cultivated over the past 20 years with care and intention. Several acres of established orchard also grace the property, producing a bounty of citrus, avocado, mango, banana, starfruit, and more—a testament to the land’s abundance and stewardship. A thoughtfully built 1,152 sq ft barn sits tucked near a private eucalyptus forest—an elegant, utilitarian complement offering exceptional potential for future use. This is more than a residence—it’s a living gallery of design, detail, and tranquility.

1642 W Kuiaha Rd, Haiku

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

$12,400,000

5 Beds ⋅ 6 Baths ⋅ 409793 MLS ⋅ Fee Simple Tenure

In 2015, a family from Idaho built this home for one purpose: to bring everyone together on the ocean in Maui. A place where children and grandchildren could land, spread out, and stay awhile. A decade later, it is offered for the first time. Fee simple, sandy beachfront on the quiet end of Halama Street, built by Smith Builders Maui with materials chosen to outlast the people who chose them. Inside, the craftsmanship is deliberate and quiet. Douglas fir wainscoting, artisan wallpaper, Rocky Mountain hardware. Five ensuite bedrooms, so everyone has their own space and no one is underfoot. The primary suite claims the entire upper level: dual closets, a dedicated office, its own laundry, and an oversized covered lanai exclusive to the upper floor. Ocean views to the front, mountain and garden views beyond. Whoever owns this home can host the whole family and still have somewhere to breathe. The kitchen, dining, and living spaces open directly to the coast. Pool, lawn, palms, then sandy beach, then ocean. The Pacific is not a backdrop here. It is the reason for all of it. The 3-car garage includes an upstairs ohana, ready for an onsite caretaker or extended family overflow. Monier tile roof, Hardie siding, copper gutters: a home that locks, leaves, and waits without complaint. Quiet enough to feel removed. Close enough to Kihei’s dining and conveniences that proximity is never a question. This is what multigenerational ownership looks like on Maui.

1536 Halama St, Kihei

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

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