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$3,985,000
4 Beds ⋅ 3 Baths ⋅ 410782 MLS ⋅ Fee Simple Tenure
5 STRUCTURE OCEANFRONT COMPOUND | OFFERED AT $ 3,985,000. An exceptional opportunity to own a private oceanfront estate overlooking breathtaking Waipio Bay in beautiful Huelo. Set behind electronic gates and surrounded by a protective hedge on 2 acres, this fully permitted sanctuary offers the rare combination of privacy, expansive ocean views, multiple living spaces, lush tropical grounds and a remarkable degree of self-sufficiency. The main residence features 4 bedrooms/3 baths, beautiful teak flooring and a Primary Suite spa inspired bathroom with a private entrance to the pool. The Primary Suite entry doors and bed are custom made from Koa Wood, adding to the tropical elegance. A large gazebo next to the main house has a private ocean view deck, shower and spa as your guests will enjoy yoga, stargazing, whale watching or cocktails at sunset with the outdoor lifestyle Maui is known for. A beautifully renovated 2 bedroom/1 bath ohana provides a private retreat for guests, extended family or tenants, with its own patio and spa and expansive ocean views. A 4-car garage includes a 1 bedroom/1 bath apartment with a deck up above. A separate Garden Cottage with a kitchen adds yet another peaceful area for naps, personal seclusion or the perfect artist’s studio. You’ll find an abundance of fruit trees, tropical flowers and a large organic garden with a nearby equipment shed to support the property’s practical side. The grounds are a true delight with a pool and waterfall feature surrounded by mature tropical, low maintenance landscaping. Designed with 2 large capacity water catchment tanks and pump house, propane for hot water and cooking, security system and established hardscape walkways, while only 30 minutes to the airport and Costco. A property of this scale, privacy, oceanfront setting and versatility is rarely offered at this price point. Come experience it in person by appointment through your favorite Realtor.

311 Door Of Faith Rd, Haiku

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

$2,690,000
4 Beds ⋅ 3 Baths ⋅ 410015 MLS ⋅ Fee Simple Tenure
Exceptional Ocean Vistas amidst your tropical paradise estate on Maui's famed North Shore.  Affectionately coined, "Hale O Peahi" this expansive custom crafted estate offers unlimited potential on a seamless level on an open facing lanai that flows out to the like-new saline pool and spa. Nestled in the highly desirable and exclusive Peahi Hui Land Subdivision on Maui's breathtaking North Shore. This expansive single-family residence offers a tranquil, elevated retreat on a generous 2-acre estate blessed with stunning ocean and mountain views from this exceptional gated estate.Hale O Peahi offers sophisticated single-level living with exceptional privacy and views. Boasting 3,576 sq ft of living space, the home features 4 bedrooms, 2.5 baths, and “pod” style architecture interconnected by covered breezeways and an expansive covered 1576 sq ft lanai. The center pod includes the open-concept gourmet kitchen, dining, and living areas — all flowing seamlessly to the outside lanai.  Plus a versatile room ideal for an office, gym, theater room, or guest suite. The master suite is elegantly tucked into its own wing, offering sweeping ocean and mountain views  The luxurious spa-style bathroom has a vibroacoustic therapy deep soaking spa tub, and just outside is a luxurious tropical shower.  The bathroom is a generous open area featuring a large walk in closet, perfectly situated near the laundry room.  The guest wing features two generous guest suites, each with expansive walk-in closets, and a well-appointed spacious bathroom.  The guest wing provides comfort and privacy, with open lanai views to the ocean and the pool. Designed for effortless living, the home features 50+ smart lightbulbs and Alexa hubs, giving you full voice-activated control of the lighting in every room.   Step outside to your own private oasis, featuring a heated salt-water lap pool with motorized cover, a jetted spa, and a bubbling fountain—perfect for relaxation or entertaining. The fully fenced grounds showcase lush Zoysia lawns, a raised-bed garden, mature tropical fruit trees, and prolific apple bananas, offering the delight of fresh-picked fruit anytime.  A quarter-acre of pasture with two charming resident goats, this property captures the essence of country living. Enjoy prime potential for a 1,500 sq. ft. second dwelling, or envision an AG barn with a second story to create expansive, flexible living or storage space. Practical amenities include a workshop/garage, storage space, a grid-tied solar PV system with Tesla battery backup, and a Solar-plus-storage setup for energy efficiency. With its carefully curated finishes, open layout, and thoughtful integration of indoor-outdoor living, this North Shore Maui hideaway captures timeless elegance, modern sustainability, and private island charm.  Don't miss these Stunning Triple Blue Views! Drop in and experience your special piece of paradise.

10 Leleaka Pl, Haiku

Listing courtesy of Century 21 Island Homes.

$3,333,000
7 Beds ⋅ 5 Baths ⋅ 409514 MLS ⋅ Fee Simple Tenure
THE MAUI SANCTUARY. Three structures. Five separate living spaces. Ocean views. Resort-style pool. Two acres of lush tropical grounds. One extraordinary Maui estate. Welcome to 1073 Nanihoku Place, a rare Hawaiian-style property in Haiku offering privacy, flexibility and luxurious resort-style living that is distinctly Maui. The property is well suited for a private family retreat, extended family and guests, creative or wellness pursuits, investment potential, or simply enjoying your own world in the heart of Maui's North Shore. The main residence features warm wood, natural light, multiple gathering areas and an abundance of indoor-outdoor living. It is thoughtfully configured into a two-bedroom plus den home, a separate two-bedroom, one-bath wing, and a ground-floor apartment with three bedrooms. A beautiful two-bedroom ohana sits at the top of the property with its own hot tub and gated entry, and is currently operated as an Airbnb. Just behind the main residence is a private 280-square-foot loft space, creating a total of five distinct living environments for family, guests and extended stays. This private tropical retreat is a must see with its amenities and endless possibilities.

1073 Nanihoku Pl, Haiku

Listing courtesy of eXp Realty.

$1,250,000
3 Beds ⋅ 3 Baths ⋅ 409390 MLS ⋅ Fee Simple Tenure
Tucked away on 1.47 lush agricultural acres in Haiku, this private property offers a rare blend of flexibility, privacy, and island charm. Public records reflect a 2-bedroom, 2-bath home, while the adaptable layout allows for multiple living options, including a potential attached studio or separate-entry unit—ideal for extended family, guests, or rental income. The home features a spacious, open feel with seamless indoor-outdoor living. Mature landscaping includes a variety of fruit trees—lime, Hawaiian lemon, coconut, banana, and sugar cane—along with puakenikeni, heliconia, and gardenia and other tropical flowers. A peaceful bamboo grove adds to the sense of serenity, tucked within the uncultivated portion of the acreage. Additional highlights include a detached structure with an Endless Pool spa and storage, extra outbuildings, and two fenced areas suited for gardening, pets, or agriculture. Set back from Holokai Road behind a gated entry, the property offers exceptional privacy in a peaceful Haiku setting. Within a 15 minute drive, are stores, schools, post office and beaches. Some images include virtual staging. Survey Completed 05/06/2026

145 S Holokai Rd, Haiku

Listing courtesy of REMAX Hawaii Maui.

$3,999,000
5 Beds ⋅ 6 Baths ⋅ 409285 MLS ⋅ Fee Simple Tenure
Situated on two privately fenced and gated acres in Haiku, Holokai Hale is a North Shore estate designed for indoor-outdoor living. More than 1,600 square feet of covered space includes lanais, walkways, and multiple areas to relax. Plumeria and puakenikeni line the grounds, with partial ocean views through the canopy. The home offers five bedrooms, six bathrooms, and over 5,000 square feet. The main residence centers on a chef’s kitchen with a large island, butler’s pantry, and direct access to covered lanais for dining and entertaining. Interior and exterior spaces connect seamlessly. The grounds include a saline pool and spa, sauna, cold plunge, and established landscaping with raised garden beds, papaya trees, banana and ginger groves, citrus, lei flowers, and a mature soursop tree. You will find vaulted ceilings and Brazilian Tiger wood floors and each bedroom includes an en-suite bathroom with the primary bedrooms Italian White Carrara Marble bathroom and extra large dressing suite. A separate guest suite provides privacy for extended stays. Additional structures include a detached workshop, an air-conditioned studio with its own sink, and a bonus room above the garage which also has a dumbwaiter. The property is supported by a 52-panel photovoltaic system, solar hot water, split air conditioning, and a whole-home backup generator. Holokai Hale is a flexible property suited for a primary residence, extended family living, or a private retreat.

65 N Holokai Rd, Haiku

Listing courtesy of Keller Williams Realty Maui-Ki.

$2,995,000
5 Beds ⋅ 3 Baths ⋅ 408773 MLS ⋅ Fee Simple Tenure
Set across 16 fully fenced and gated acres in Ha'iku, this expansive Maui estate offers privacy, substantial infrastructure, multiple structures, and considerable flexibility. The property is served by a County of Maui 5/8-inch water meter and a high-capacity well nearing completion, and is potentially subdividable subject to applicable County approvals. More than 20 varieties of mature exotic fruit trees and flowering plants are established throughout the grounds, with walking paths connecting the residences and amenities. At the center of the property is a 5,000+ square-foot main residence with five bedrooms, three bathrooms (two are large/bathhouse style), and a spacious commercial-type kitchen. The primary suite is surrounded by walls of glass overlooking the tropical landscape. The living room features a fireplace and concealed projection screen, while a large screened lanai provides additional space for dining and entertaining. A landscaped courtyard with a cascading waterfall and koi pond leads to trails winding throughout the property. A separate commercial-grade kitchen, adjoining screened gathering area, and dedicated men's and women's bathhouses reflect the property's history as a retreat destination and provide additional flexibility for larger gatherings. Additional structures include a two-room cottage currently used as an office, an upper guest cottage with a private outdoor shower house, and a separate two-story building tucked toward the rear of the acreage. These spaces provide options for guests, offices, studios, workshops, storage, or other uses. Outdoor amenities include a resort-style swimming pool with a waterfall and slide, pool house, massage pavilion, and extensive landscaped grounds. The estate is offered fully furnished, including more than $150,000 in furnishings, artwork, and antiques, with appraisals available. With 16 acres, multiple structures, established infrastructure, extensive landscaping, and potential subdivision opportunities, this Ha'iku property offers a range of possibilities as a private estate, multigenerational compound, creative retreat, or long-term Maui investment.

1055 Kaupakalua Rd, Haiku

Listing courtesy of Hawaii Life (W).

$7,450,000
3 Beds ⋅ 2 Baths ⋅ 408161 MLS ⋅ Fee Simple Tenure
Seller is now offering FULL ownership in this truly irreplaceable North Shore Maui oasis. Set amid panoramic ocean, coastline, and waterfall views, this sanctuary offers rare natural resources and privacy. Enter through hand-crafted 24-foot custom gates into a double-fenced private estate featuring 6 permitted structures thoughtfully designed with a blend of Japanese, Hawaiian, and Balinese architectural influences. Improvements include a dedicated ag center, office/garage, infrared sauna, custom loft, and multiple living spaces that harmonize seamlessly with the surrounding landscape. A stone walking path encircles the property, guiding you through a stunning rainbow eucalyptus forest, paperbark tree grove, and a variety of producing trees including cherry, papaya, banana and more. A wrap-around driveway with parking for 20+ vehicles makes the estate ideal for hosting gatherings and entertaining family/friends. This self-sustaining retreat features a 280-foot private well with county water rights, nutrient-rich soil ideal for agriculture, and owned solar with commercial-grade infrastructure. Enjoy ocean and waterfall access from the property! An opportunity to fully own one of Maui’s most inspiring and unique estates—Don’t miss out!!!

180 Door Of Faith Rd, Haiku

Listing courtesy of eXp Realty.