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$2,100,000
5 Beds ⋅ 3 Baths ⋅ 410578 MLS ⋅ ACTIVE Status
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.

$3,999,000
5 Beds ⋅ 6 Baths ⋅ 409285 MLS ⋅ ACTIVE Status
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.

$3,250,000
5 Beds ⋅ 5 Baths ⋅ 408964 MLS ⋅ ACTIVE Status
North Shore paradise. Brand New Construction 5 bdr/ 5 bath with sweeping Ocean Views. Desirable neighborhood in Haiku. Two story home with a dramatic 2 story entryway with luxurious floating stairway and modern chandelier. 10 foot ceilings on first and second floor. Gourmet kitchen with Thermador appliances and quartz counters. Beautiful modern cabinetry. Walk in pantry with bonus freezer. Oak engineered hardwood throughout. Indoor outdoor living at its best with 16 foot sliding pocket door. Outdoor BBQ area. One bedroom or office downstairs with a full bath ensuite. Upstairs enjoy a large laundry room, jack n jill bedrooms with adjoining bathroom and a breathtaking primary suite with double door entry, lanai access, breathtaking views, expansive closet, large shower, separate soaking tub, and toilet room. The 5th bedroom upstairs with ensuite bathroom and separate entryway could be a flex space for a MIL suite, office, or rental opportunity. Smart home, SONOS 10 zone speaker system and security cameras. Split AC throughout. Gated driveway. Two car garage. Unit A of a new developer offering 2 unit CPR. Total land for the TMK 1.308 acres. Unit A is 0.643 acres. 10 minutes to Hookipa Beach Park and restaurants at Haiku Cannery. 15 minutes to shopping and restaurants in Paia. Listor is owner. No HOA.

111 Mehana Rd Unit Unit A, Haiku

Listing courtesy of The Maui Real Estate Team Inc.

$2,995,000
5 Beds ⋅ 3 Baths ⋅ 408773 MLS ⋅ ACTIVE Status
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).

$2,900,000
5 Beds ⋅ 3 Baths ⋅ 408644 MLS ⋅ ACTIVE Status
Also listed as Single Family w/ Det Ohana or Cottage Res - MLS# 408817 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.