Makawao/Olinda/Haliimaile Homes with Detached Ohana

Makawao/Olinda/Haliimaile Homes with Detached Ohana

**Discover the Enchantment of Makawao/Olinda/Haliimaile**

Nestled in the heart of Maui, the charming districts of Makawao, Olinda, and Haliimaile offer a unique blend of rustic charm and breathtaking natural beauty. Known for their lush landscapes, these areas are a haven for those who appreciate the serene lifestyle of upcountry Hawaii. With cool temperatures, vibrant greenery, and stunning views of both the Pacific Ocean and the majestic Haleakal?, residents of this region enjoy a tranquil escape from the hustle and bustle of coastal living.

Makawao, a historic paniolo (cowboy) town, is rich in culture and community spirit. Its charming storefronts, art galleries, and local eateries create a warm, inviting atmosphere that draws both locals and visitors alike. Just a short drive away, Olinda boasts expansive ranches and serene residential neighborhoods, perfect for those seeking peace and privacy. Haliimaile, known for its agricultural roots, offers a delightful mix of residential homes and scenic landscapes, making it an ideal spot for families and nature lovers.

One of the standout features of homes in this area is the availability of detached Ohana units. These charming accessory dwelling units provide additional living space, perfect for extended family, guests, or even as a rental opportunity. With the flexibility that Ohana homes offer, residents can enjoy the benefits of multi-generational living while maintaining their own privacy.

Whether you’re looking for a cozy retreat or a family home with room to grow, the Makawao/Olinda/Haliimaile district is a hidden gem waiting to be discovered. Embrace the spirit of Aloha and explore the possibilities of calling this enchanting region your home!

Newest Makawao/Olinda/Haliimaile Homes with Detached Ohana

$2,649,000
5 Beds ⋅ 4 Baths ⋅ 410159 MLS ⋅ Fee Simple Tenure
Crest the rolling hills and you’ll discover this breathtaking Upcountry Maui estate: a one-of-a-kind property with a rare combination of privacy, expansive space, and timeless charm. The property lies on 4.38 acres of vibrant, open land. It could be your own little oasis, with lush landscaping and tranquility within a short driving distance to charming Makawao Town. The main residence is custom-built with rich redwood walls on both the interior and exterior, a dramatic fireplace hearth formed from black lava rock, teak bannisters, and other handcrafted architectural details throughout. The brand-new deck stretches around the home, providing glorious views of both the mountains and the North Shore. This home was built with love, and the living experience is sure to be warm and absolutely unforgettable. Beyond the primary residence, this property boasts a separate cottage with its own private entrance. This second dwelling offers exceptional flexibility for guests, extended family, or even rental potential.

1740 Piiholo Rd, Makawao

Listing courtesy of Coldwell Banker Island Prop(S).

$2,395,000
5 Beds ⋅ 4 Baths ⋅ 409724 MLS ⋅ Fee Simple Tenure
This unique multi-unit property (4 structures, 8 units) offers a rare opportunity for investors seeking strong cash flow and long-term upside. There are 5 one bedroom units, and 3 two bedroom units. Situated on just over half an acre, the property features four separate structures with a total of eight tenant-occupied units, creating an income-producing compound in one of Upcountry Maui’s most desirable locations. Tenants enjoy dedicated parking, on-site laundry, and the convenience of being moments from Makawao’s shops, restaurants, galleries, and local charm. Numerous improvements have already been completed, making this an attractive opportunity for an investor looking to step into an established rental property with immediate income potential. The property also has 3 water meters. Listing includes photos of one of the 8 units. A truly one-of-a-kind upcountry investment property.

15 Olinda Rd, Makawao

Listing courtesy of eXp Realty.

$4,750,000
3 Beds ⋅ 4 Baths ⋅ 409873 MLS ⋅ Fee Simple Tenure
This 10 acre Piiholo property at 4,000' elevation borders a 41-acre State forest and has incredible ocean and mountain views. The very distinctive and extraordinary main residence, designed by renowned architect Jim Hestand of Maui Architectural Group, is an absolute work-of-art. Almost entirely constructed with old-growth redwood, the architectural inspiration was designed for the well-known concerts and poetry gatherings among the owners in the days of its grandeur...a true legacy property. The main home has recently been thoroughly and lovingly returned to its original beauty and beyond, with the remodeling and modernizing of the kitchen and bathrooms. All of the out-buildings, concrete driveway and landscaping have also been restored. Rare peace and privacy are assured within the grounds. The 2nd residence is reminiscent of a mountain cabin vibe. The 2 residences are separated by many usable acres of trees and orchards. One could certainly imagine this property being ideal for horses. In between the two homes there is an artist/musician studio with flexible use. There are 2 water meters, serving each end of the property. Additionally, there is a large garage/workshop and a useful farm structure. Pi'iholo, is known for cool days and cooler evenings with passing mists, reliable rainfall and refreshing trade winds. There are several respected public schools and excellent private schools in the region. Farmers markets, supermarkets and roadside stands assure you can keep your shopping Up Country. The range of restaurants is remarkable. And for health care, Up Country has it all.

2450 Piiholo Rd, Makawao

Listing courtesy of Coldwell Banker Island Prop(P).

$2,150,000
4 Beds ⋅ 3 Baths ⋅ 409809 MLS ⋅ Fee Simple Tenure
Spacious, private, and full of character, 25 Lumahai Place, just off Olinda Road, sits on 2.88 acres with sweeping ocean and West Maui mountain views, cool fresh air, and temperatures that feel like spring year round. A 2,732 square foot main home and detached cottage, 5-7 minutes from Seabury Hall and Makawao Town. The main home's soaring wood-beam ceilings and wood-burning fireplace set a warm, welcoming tone from the moment you walk in. The living and dining areas flow naturally to a the lanai where the views take center stage. The kitchen is generous in size, flooded with natural light, and thoughtfully appointed with granite and butcher block countertops, a farmhouse sink, walk-in pantry, and a picture window perfectly framing the landscape outside. New refrigerator and stove were added in 2026, along with an updated under-sink water filtration system. A solar PV system with battery storage keeps energy costs in check. The primary suite is privately situated with vaulted ceilings, a gas stove, and a beautifully updated ensuite featuring dual vanities, walk-in shower, and soaking tub. Fresh paint and a fully redone second bathroom reflect the care and attention put into this home. Two additional bedrooms, a dedicated laundry room, built-in storage, and a finished loft, ideal as a library, playroom, or fun creative space, complete the main level. Downstairs, a separate 1-bedroom, 1-bath space with its own entrance and newly added sliding door offers excellent flexibility for guests, extended family, or a home office. The recently remodeled detached cottage has its own driveway, parking area, and cement stairs, providing true separation and privacy, and built to last. Perfect for multigenerational living, long-term guests, or rental income. Extensive eucalyptus clearing has opened up the property, improving views, natural light, and usable space while preserving its peaceful Upcountry character. Wake to birds singing and fall asleep to the sound of wind moving through the trees.

25 Lumahai Pl, Makawao

Listing courtesy of Compass-W.

$1,795,000
4 Beds ⋅ 1 Baths ⋅ 409572 MLS ⋅ Fee Simple Tenure
Discover a rare opportunity to own approximately 11.3 acres in the peaceful Hali’imaile/Makawao area. This private agricultural-zoned Lot A CPR parcel offers ocean and mountain views, cool breezes, and a true Upcountry ranch feel. Located within the Kaluanui Ridge 7-lot subdivision, the property is conveniently positioned between Makawao and Paia, with approximately a 5-minute drive in either direction. At an elevation of about 1200 ft this area reportedly gets an average of about 59 inches of rainfall per year and mostly sunny days all year round. This spacious property offers the privacy, open space, and quiet rural lifestyle that make Upcountry Maui so desirable. The land is mostly fenced and includes an approx. one-acre fenced animal pasture, making it well suited for livestock, farming, homesteading, or creating your ideal Maui country retreat. The lot also borders a drainage reserve, providing additional privacy and a natural buffer. Two existing container home dwellings are already in place. The larger dwelling features 4 bedrooms, a kitchen, bathroom, 40ft storage container, off-grid solar system with 21 PV panels, inverter setup, and roughly 14 kWh of 48V battery storage, and an 800-gallon water catchment system. The second container dwelling includes 2 bedrooms, 1 bathroom, kitchen, and catchment system, with power available by generator or from the main solar setup. Enjoy privacy, acreage, views, and the peaceful beauty of Maui’s Upcountry lifestyle—all while remaining close to town, beaches, schools, shops, and conveniences.

2759 Baldwin Ave Unit 7 F A, Makawao

Listing courtesy of Hawaii Life (W).

$3,400,000
4 Beds ⋅ 3 Baths ⋅ 409325 MLS ⋅ Fee Simple Tenure
If home is where your horse is, try imagining yourself on this 9.618-acre ranch in the heart of Maui's cowboy town, Makawao! With a 16-stall horse barn and a climate-controlled tack room, a huge riding arena used for horse shows, training, and riding lessons, and farm buildings filling every corner, this has been a working ranch for the last 25 years. The primary dwelling was originally built as a barn but was converted into a 4-bedroom, 3-bath, 2,914 sq. ft. amazing home with windows looking out on the ranch as well as barn-high ceilings that give a spacious feeling to the heart of the house! Enjoy extreme comfort with cooling and heating mini-splits in every room! Wind down the rustic center spiral staircase to the mother-in-law style lower-level, where you'll find 2 of the bedrooms and the laundry room. Across from the main arena is the original home that is now a completely rebuilt cottage with a large attached studio... a great place for a ranch manager to live. The possibilities are endless with this versatile property!

61 Kee Rd, Makawao

Listing courtesy of Equity One Real Estate Inc (M).

$1,495,000
3 Beds ⋅ 2 Baths ⋅ 407661 MLS ⋅ Fee Simple Tenure
Welcome to 1199 Freitas Place in Makawao town — a well-cared-for home that combines functional design with classic island living. This is truly one of the best values in Makawao on a $/sf basis! The property features a 1635 square foot, 3-bed/2-bath main residence and a 667 square foot detached Ohana. Both structures are situated on a lush 0.39 acre corner lot with established fruit trees and versatile outdoor spaces. The main home has been freshly repainted and maintained with great attention to detail. Its thoughtful layout provides a welcoming atmosphere with space for relaxation and entertaining. The separate Ohana, previously used as a hair salon, offers an open floor plan ready to be tailored to your needs — whether as an additional living area, creative workspace, or guest suite. The fenced-in yard showcases a diverse fruit orchard featuring mountain apples, oranges, tangerines, lemons, limes, bananas, peaches, curry leaf, Suriname cherries, ginger and turmeric. Additional structures include a workspace and storage shed, offering flexibility for hobbies or projects, an ocean view deck for relaxing or sunset dinners, and a large generator to keep the home fully powered during outages. The dryer, cooktop and oven are all gas powered. Owners average electric bill has been less than $100/month! Located within walking distance of Makawao Town and Makawao Elementary School, you’ll enjoy the convenience of local shops, dining, and community events, all while feeling tucked away in your own private oasis. This is a property that’s been genuinely cared for, offering a lifestyle that blends nature, creativity, and Maui comfort.

1199 Freitas Pl, Makawao

Listing courtesy of Compass-W.

$1,825,000
4 Beds ⋅ 3 Baths ⋅ 407512 MLS ⋅ Fee Simple Tenure
Discover Hokuula in the quaint town of Haliimaile, nestled on the gentle slopes of Haleakala, overlooking Maui’s world-renowned Northshore coastline. Expansive ocean and mountain views will greet you from this soon to be Upcountry community of 196-single family homes. Featuring contemporary architecture with six unique, 4-bedroom models on lots of approximately 7,500 to 10,000 square feet. Hokuula offers a variety of diverse floor plans in single and two-story designs. In addition, ohana dwellings are available on various lots, providing even more versatility. Each home has been thoughtfully designed. This single-story Floor Plan A home has 4 bedrooms and 3 bathrooms. Features include an open floor plan, 9 foot ceilings, split AC, rain gutters, covered lanai, attached two car garage. Highlighted amenities consist of stainless-steel appliances, double paned windows, soft close cabinetry. A walking path around the perimeter of the community will provide another way to enjoy the panoramic views from Hali?imaile. Located just a few minutes from the modern conveniences of Kahului as well as the quaint charms of Paia and Makawao. This is truly a unique opportunity to own your piece of paradise on Maui, a wonderful place to call home. Developer reserves the right to modify floor plans, elevations, specifications, features, and prices without prior notice. Square footage and room sizes are approximate. All renderings and floor plans are conceptual and are not intended to be an actual depiction of the home, driveway, or landscaping. Prices vary between floor plan and lot selections along with view corridors. Buyer and Buyer's Agent to conduct due diligence.

179 Maiaku St Unit Lot 165, Makawao

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

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