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$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
Also listed under Multi-Dwelling (MLS 409725). 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.

$1,365,000
2 Beds ⋅ 2 Baths ⋅ 410052 MLS ⋅ Fee Simple Tenure
Looking for a home with multi-generational living options or a mortgage helper? Look no further than 191 Alohilani. This two-bedroom, two-bath home and two-bedroom, one-and-a-half-bath cottage offer the perfect setup and much more. The well-cared-for main home includes a covered, screened lanai with ocean and mountain views, an owned solar system to keep electric bills down, and a flex room that could serve as a third bedroom, hobby room, or home office. A covered hot tub is a great place to watch the sunset and melt away the day’s cares. There is plenty of storage area between a large closet off the carport and a separate shed for all your yard tools or Maui toys. The cute and cozy cottage has its own lanai area with views of Haleakala, the West Maui Mountains, and the ocean. The well-landscaped property offers a mix of beautiful flowers, edibles, and native plants. Handsome stone terraces at the front of the property are interspersed with lime, sugar cane, kalo (taro), pohole fern, starfruit, ohia, papaya, banana, and a variety of herbs. The property’s convenient location is within walking distance of Pukalani Park, the Upcountry Pool, and Pukalani Terrace Shopping Center. It is a short drive down Haleakala Highway to Central Maui or North Shore Beaches. It all comes together as a tidy, move-in-ready package for Upcountry Home buyers. Contact your favorite Maui Realtor to set up a showing today.

191 Alohilani St, Makawao

Listing courtesy of The Maui Real Estate Team Inc.

$1,479,000
3 Beds ⋅ 3 Baths ⋅ 409999 MLS ⋅ Fee Simple Tenure
This property really is a little gem. It has been well cared for and ready for a buyer that wants a turnkey move in experience. The location is super convenient with easy access to Pukalani Terrace Shopping Center and Pukalani Superette, and approx. a 15-minute drive to Kahului. It features many upgrades including but not limited to, tub to shower conversions in the main house and ohana, beautifully retiled pool with ceramic tiles with a new heating system installed in 2026, the main house interior walls are newly plastered, also a full kitchen remodel and new flooring throughout the main house. The back deck overlooks the pool and is great for outdoor entertaining and summertime pool parties and the backyard is fully fenced and secure from off property access. The 2nd home ohana features a walk-in pantry, easy access to a spacious back yard and covered lanai off the primary bedroom, and a covered gazebo for outdoor gatherings.

3260 Kihapai Pl, Makawao

Listing courtesy of Welcome Hawaii Properties.

$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).

$895,000
3 Beds ⋅ 1 Baths ⋅ 408706 MLS ⋅ Fee Simple Tenure
AS-IS sale. Rare opportunity in Pukalani, located next to Old Haleakala Highway. This approximately quarter-acre (11,155 sq ft) property features two dwellings. The main house offers approximately 720 sq ft with 3 bedrooms and 1 bathroom and requires major renovation. It is currently being used for storage and is not in livable condition. The half bathroom and garage remain as foundations only. The ohana unit is approximately 600 sq ft with 2 bedrooms and 1 bathroom, offering excellent rental income potential. Both dwellings are connected to cesspools. Conveniently located with a restaurant next door and a gas station across the street. Grocery stores, restaurants, coffee shops, and banks are all within one mile, providing everyday convenience.

3321 Old Haleakala Hwy, Makawao

Listing courtesy of eXp Realty.

$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).