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$2,100,000
5 Beds ⋅ 3 Baths ⋅ 410578 MLS ⋅ Fee Simple Tenure
Discover a rare property offering flexibility, privacy, and strong income potential. Situated on approximately 2 acres of agriculturally zoned land in Haiku, this unique estate features multiple dwellings—ideal for multi-generational living or rental use. Conveniently located just a short drive to Haiku Town, Makawao, the North Shore, and world-renowned surf at Ho‘okipa and Paia. The main residence offers 5 bedrooms, 3 bathrooms, and a 1-car garage with its own private yard. A second home includes 4 bedrooms, 3 bathrooms, and a 1-car garage, thoughtfully positioned to provide separation and privacy, with multiple private entrances for flexible use. At the rear of the property is an original plantation-style home with 4 bedrooms and 1 bathroom, along with an additional structure featuring expansive floor-to-ceiling glass panels—ideal for an office, studio, or creative workspace with mountain views. The grounds feature a variety of tropical fruit trees, including mango, mountain apple, loquat, lychee, and avocado, along with bamboo, palms, and flowering plants such as ginger and gardenia. There is ample space for farming, gardening, or future improvements. Additional features include two water meters, one cesspool, and one septic system. A versatile property with multiple use options. Contact your Realtor today to schedule a private showing

2615 Kaupakalua Rd, Haiku

Listing courtesy of Royal Realty LLC.

$2,700,000
3 Beds ⋅ 5 Baths ⋅ 410469 MLS ⋅ Fee Simple Tenure
This phenomenal slice of paradise was appraised for $2,700,000.00 (Listed price), in July 2026. It consists of 5.05 Splendid acres on an AG Zoned parcel, in the heart of Haiku. Emerald green pastures dotted with various fruit trees, flowers, and room for horses, sheep, goats, chickens, etc. This Legacy property is as close to heaven on earth, as can be. The owner/ builder imagined everything with a purpose, and it shows in the quality upgrades throughout the Main home and property. Lychee, coconut, mango, mountain apples, and avocado trees are a few of the trees that frame the acreage, and make for wonderful eating. The Lychee were planted so that they would stagger bloom every other year. The flowers are a variety of Hibiscus, Gardenias, and several other fragrant, and tropical treasures!! The farm also features a small barn, and extra tool shed. Construction includes vaulted ceilings, a large covered exterior living area, featuring a kitchen, great space to watch sports, and large windows taking in the verdant lawns, in addition, another fabulous wrap around lanais, with yet another barbeque covered lanais. This owner built main home, boasts everything you need to run a farm/ranch, and then some. The 4064 sq. ft., Main home is a large single- story home, constructed on post and piers. The home is on a slight hillside, permitting for a large under- home work shop, providing both power, and water, as well as an extra half bath, for the workers. Main home features multi-generation living. It boasts 2 large kitchens, 3 En Suite Bedrooms, an extra full, and half bath, a media room, library, a large den, formal full bar, and separate office. All the bedrooms are equipped with TV access. Included are several large aquariums, which will remain in the main home. The sellers have installed an electric gate for access to the main home. There is a separate entrance to the cottages. There are also two fully permitted 1000 square foot, 3 bed 2 bath - cottages. One of the cottages features a 2-car garage. These cottages are tenant occupied, and are now rented on a month- to- month basis. The main home, and one of the cottages are equipped with Photo voltaic panels. The property is on one water, and electric meter. Qualified buyers may arrange to view the property, keeping in mind, that a 48 hour -notice is required to view the Ohanas. The property is being sold AS IS. The current Owner/Trustee was not on site when the property was built. The Trustee who built it, passed away in 2016, so Seller’s Disclosure will be limited.

1525 Kaupakalua Rd, Haiku

Listing courtesy of Coldwell Banker Island Prop-KP.

$2,190,000
3 Beds ⋅ 3 Baths ⋅ 409783 MLS ⋅ Fee Simple Tenure
Gated North Shore estate featuring two substantial dwellings on 2.181 private acres in desirable Haiku Country Estates. Offering approximately 3,481 square feet of combined living area, this exceptional property blends privacy, flexibility, and income potential in one of Maui’s most sought-after rural communities. The main residence is a beautifully crafted Lindal Cedar home offering 3 bedrooms and 3 bathrooms across approximately 2,482 square feet. Thoughtfully updated over the years, including a major renovation in 2017, recent improvements include updated flooring, new garage doors, and refreshed lanai spaces. Its versatile layout provides multiple living areas ideal for extended family, guests, or additional rental opportunities. Built in 2019, the separate 999-square-foot, 2-bedroom, 2-bath ohana is privately situated near the front of the property and offers excellent flexibility for long-term rental income, multigenerational living, or guest accommodations. Adding even more value, a County-approved building permit issued February 5, 2025, allows for an approximately 500-square-foot addition to the ohana, creating future expansion potential without the uncertainty of starting the permitting process. Bordered with mature bamboo for exceptional privacy, the agriculturally zoned property is beautifully landscaped with an abundance of established fruit-bearing trees, including lychee, mango, avocado, banana, macadamia, coconut, pomelo, orange, and a variety of citrus, creating your own tropical orchard and island sanctuary. This rare offering combines lots of usable acreage, two quality residences, expansion potential, privacy, and lifestyle—all just minutes from Haiku Town, world-class beaches, surfing, hiking, and everything Maui’s North Shore has to offer.

2695 Lia Pl, Haiku

Listing courtesy of Kokua Realty LLC.

$9,500,000
6 Beds ⋅ 6 Baths ⋅ 409677 MLS ⋅ Fee Simple Tenure
Welcome to 1949 W Kuiaha Rd: a rare opportunity to acquire a one of a kind, legacy Maui country estate within one of the most beautiful microclimates of all the Hawaiian islands. On 39 acres of pristine land, two skillfully crafted homes look out onto expansive, gently sloping green pastures with full panoramic ocean views.  Enjoy tranquil ocean, garden & mountain views from the entire downstairs great room as well as from the 818 sq ft covered lanai of the 4 bed 3.5 bath main home. Notable features are massive beam construction, Venetian plaster walls, a 1050 sq ft Primary suite with a fireplace, clawfoot tub & its own 756 sq ft private Ipe deck with incredible ocean views, a 659 sq ft multipurpose room with its own stairwell entrance, a 200 sq ft office, a 1933 sq ft garage, 531 sq ft of storage & an owned PV system. Just beyond the bamboo grove is a quaint 2 bed/2.5 bath, 1495 sq ft cottage which features a stunning 586 sq ft covered lanai & Ipe deck offering prime ocean views, Monkeypod slab counters in the kitchen & living room, a fireplace, 2 offices, semi outdoor shower & a gorgeous vaulted cupola roof. In addition, there are 4 fenced pastures, 2 partially enclosed sheds totaling 782 sq ft, 1 garden shed, 3 additional loafing sheds & a hitching post. The impressive array of fruit & ornamental trees, Rainbow Eucalyptus & Cook Pine forests, 2 acre garden, a seasonal stream, 3 property entrances, inspiring Haleakala, Giggle Hill, West Maui mountain & Pacific ocean views, incredible privacy, immersion in nature, general potential & future value that this property offers is unlike any other. There is much to explore, enjoy & create. This property is an equestrian’s and rancher's dream. 1949 W Kuiaha Rd is well-positioned in Haiku Pauwela with close proximity to Haiku, Makawao & Paia towns, Baldwin beach, Twin falls, exceptional schools, the best farmer’s markets on the island, private & international airports.  This property is a gem & must be seen in person to appreciate.  Seller is open to selling all or part of the property: A four unit CPR is in progress. Once completed, individual lots will be available to purchase separately at an elevated value. Seller may be open to trades. Contact Listing agent for more information. Listing agent is related to Seller.

1949 W Kuiaha Rd, Haiku

Listing courtesy of Hawaii Life (MA).

$1,695,000
3 Beds ⋅ 3 Baths ⋅ 409579 MLS ⋅ Fee Simple Tenure
Tucked away on approximately two acres in the heart of Haiku, this unique multi-dwelling property captures the timeless feeling of old Maui. A long private driveway winds through mature tropical landscaping and fruit trees, revealing expansive valley, gulch, and West Maui Mountain views. The upper 4-bedroom, 2-bath residence overlooks Maliko Gulch and features a recently installed roof. The property also includes a newer 2-bedroom, 1-bath ohana with a remodeled attached studio, two adjoining tiny homes connected by a custom deck, and a privately situated lower 3-bedroom, 2-bath residence. Together, these living spaces offer exceptional flexibility for extended family, guests, creative workspace, or other possibilities. Some areas offer an opportunity for cosmetic updating and personalization. Located just minutes from beaches, restaurants, shopping, and Maui’s North Shore communities. The neighboring 2.4-acre property is also available separately, creating the potential to own approximately 4.4 combined acres.

1640 Kokomo Rd, Haiku

Listing courtesy of KM Brokerage LLC.

$1,795,000
3 Beds ⋅ 2 Baths ⋅ 409577 MLS ⋅ Fee Simple Tenure
Tucked away on approximately two acres in Haiku, this unique multi-dwelling property offers privacy, versatility, and expansive views of Maliko Gulch, the valley, and West Maui Mountains. The upper 4-bedroom, 2-bath residence features a recently installed roof. Additional living spaces include a newer 2-bedroom, 1-bath ohana with a remodeled attached studio, two adjoining tiny homes connected by a custom deck with shared kitchen and bath facilities, and a privately situated lower 3-bedroom, 2-bath residence. Surrounded by mature tropical landscaping and fruit trees, the property offers flexible possibilities for extended family, guests, creative space, or rental income. Some areas provide an opportunity for cosmetic updating and personalization. Conveniently located near beaches, shopping, restaurants, and Maui’s North Shore communities. The neighboring 2.4-acre property is also available separately, creating the potential to own approximately 4.4 combined acres.

1660 Kokomo Rd, Haiku

Listing courtesy of KM Brokerage LLC.

$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.

$2,900,000
6 Beds ⋅ 3 Baths ⋅ 408817 MLS ⋅ Fee Simple Tenure
Also listed as Multi-Dwelling Res - MLS# 408644 Owner financing with 65% down. This property is majestic and unique. One of a kind!!! Perfect for Estate Living or farming. Zoning is commercial/AG A-1 Plan for your families future. Several opportunities. Welcome to Bamboo Valley Haiku, Maui. This Maui estate, located in a hidden tropical valley and bordered by a year round flowing stream is the ultimate in privacy and seclusion. At the heart of the estate is a custom 6 bedroom, 3 bath main residence and 1 bdrm detached cottage currently operating as Bamboo Valley Inn - loved by travelers from around the world. The main home offers exceptional privacy and exquisite design elements set upon an incredible backdrop of raw natural beauty. With no homes in sight, the property captures the essence of North Shore living- peaceful, tropical, powerful and refined. 3 cozy fireplaces complement the tropical atmosphere on cool north shore nights. The expansive covered lanai has tremendous views creating an idyllic setting for outdoor dining, entertaining and relaxing. The gated entry leads to a meandering stone driveway ensuring tranquility, security and seclusion. Tucked away approximately 100 yards from the main home, and beautifully concealed behind swaying bamboo, you will discover the charming Polynesian style pole home cottage. This home is full of architectural character containing custom lava rock features throughout, wrap around lanais and an open design creating a strong indoor-outdoor Hawaiian lifestyle. Both homes contain large windows that dissolve the boundaries between indoor and outdoor, so light pours in from every direction and the tropical forest and landscape become part of the interior decor. Without ever leaving the property you can enjoy a peaceful stroll through an exotic bamboo forest on a groomed trail which leads to the year round stream. This is more than an estate - it is a tranquil retreat where nature and comfort blend seamlessly. Spacious, quiet and surrounded by beauty, this Haiku property offers a lifestyle that is increasingly hard to find in the heart of Haiku, Maui. This property is being offered fully furnished with quality, move-in ready furnishings.

1444 W Kuiaha Rd, Haiku

Listing courtesy of Nathalie Mullinix Rlty Universal Inc.

$11,900,000
3 Beds ⋅ 4 Baths ⋅ 408784 MLS ⋅ Fee Simple Tenure
Above a quarter mile of untouched North Shore coastline rises a rare opportunity to own one of Maui’s most extraordinary oceanfront estates. 400 Mehana Road commands sweeping 180 degree views of the Pacific from its elevated perch 275 feet above the sea. From sunrise to moonrise, panoramic ocean views create a constantly evolving backdrop to daily life. The 5,403 square foot primary residence offers 3 bedrooms and 3.5 bathrooms, thoughtfully positioned to embrace the extraordinary setting from nearly every room. Soaring coffered ceilings and expansive windows frame the ocean beyond, while newly installed bamboo flooring adds warmth and natural texture. Motorized shade screens provide comfort and ease, allowing the interiors to transition effortlessly throughout the day. The chef’s kitchen is both striking and functional, anchored by dual islands finished in black India leathered granite, creating a natural gathering space for entertaining or quiet evenings at home. A separate 1,050 square foot cottage with 1 bedroom and 1.5 bathrooms sits discreetly above the bluffs, privately tucked away from the main residence. Ideal for guests, extended family, or a creative retreat, it offers flexibility without compromising the estate’s sense of privacy and scale. Just fifteen minutes from town and easily accessible off Hana Highway, the property offers a rare balance of seclusion and connection. Some of Maui’s most respected private schools, including Seabury Hall, Montessori, Carden Academy, and Waldorf High School, are all within a short drive, adding meaningful convenience to this exceptional lifestyle. Spanning 20.5 acres, the grounds unfold with open lower meadows suited for equestrian use, irrigated gardens, and an edible orchard. A 293 foot well and a 5/8 inch County water meter provide reliable water resources. Along the eastern boundary, an enchanting 80 foot waterfall cascades toward the shoreline, creating a natural habitat for native Hawaiian green sea turtles. Private access to a secluded rocky beach enhances the rarity of this exceptional Maui estate. This is more than a home. It is a legacy estate where privacy, natural grandeur, and architectural presence come together in one of Maui’s most extraordinary coastal settings.

400 Mehana Rd, Haiku

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

$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).

$2,995,000
3 Beds ⋅ 2 Baths ⋅ 408713 MLS ⋅ Fee Simple Tenure
Set on 5.017 private acres in Haiku on Maui's North Shore, 30 Mamao Place offers an established setting for buyers drawn to acreage, privacy and a modern homestead lifestyle. Multiple microclimates, a large fenced garden, mature fruit trees, barn with tack room, chicken coop and fire pit create real opportunities to grow food, care for animals and live more closely with the land. A mature areca palm hedge surrounds the property, creating a sense of being far removed, with the airport still approximately 30 minutes away. The 3-bedroom, 2-bath custom cedar home offers approximately 2,430 sq ft with soaring ceilings, handcrafted woodwork, a chef's kitchen with oversized Wolf range, and a screened lanai looking across the acreage. A great room with 20+ ft ceilings adds volume and a striking gathering space. A detached office supports remote work, while a 2,500 sq ft steel workshop with half bath and separate electric meter provides exceptional project, equipment and storage space. Two additional garages include a 1-bedroom, 1-bath living area and a separate studio with loft. Concrete drives connect the buildings, with generous separation creating privacy throughout. Equally suited for full-time living or as a private Maui second home, this Haiku acreage property offers a combination that would take years to recreate. Private showings are available now.

30 Mamao Pl, Haiku

Listing courtesy of West Maui Land Company Inc.

$870,000
2 Beds ⋅ 2 Baths ⋅ 406950 MLS ⋅ Fee Simple Tenure
Recently appraised at $1,100,000. Submerse yourself into nature and drop down (literally) into paradise at this incredible 3-acre property. There is so much more than meets the eye here. Feel the mana as you descend the switchback trail into sacred grounds and find a lovely home, and several other "jungelows" and out buildings. A tropical breeze swirls around in this valley, keeping it cool and climate friendly. You are completely surrounded by greenery and there is a flowing stream that separates the 2 dwellings nicely. There are many mature fruit trees, beautiful gardens and gorgeous flowers...a truly sustainable property. Slow down and take it all in as you escape to this heaven on earth. Structures have been brought up to county code and are waiting on permits. Access is via a switchback trail. There is no driveway access.

106 Hikiau Rd, Haiku

Listing courtesy of Coldwell Banker Island Prop(P).