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$1,450,000
5 Beds ⋅ 4 Baths ⋅ 410362 MLS ⋅ Fee Simple Tenure
Exceptional multi-generational living or investment opportunity in the heart of Pukalani! Situated on a generous 10,000 sq. ft. lot overlooking the 13th hole of the Pukalani Golf Course, this versatile property offers multiple living spaces, beautiful golf course views, and energy-efficient upgrades. The main residence features a beautifully remodeled single-level 3-bedroom, 2-bath home (updated in 2026) with modern finishes and comfortable living spaces. Upstairs, you'll find a spacious 880 sq. ft. 2-bedroom, 1-bath unit complete with a 176 sq. ft. covered deck, providing a peaceful setting to relax and enjoy the surrounding views. A separate 420 sq. ft. ground-level studio at the rear of the property is currently tenant-occupied, offering excellent income potential. The home is equipped with 62 owned photovoltaic (PV) panels and backup batteries, helping to reduce energy costs while providing added peace of mind. Whether you're looking for a primary residence with rental income, a multi-generational home, or an investment property, this unique Pukalani offering delivers flexibility, location, and value. Enjoy the convenience of Upcountry living with schools, shopping, dining, parks, and community amenities just minutes away.

2806 Iolani St, Makawao

Listing courtesy of Compass.

$839,000
4 Beds ⋅ 3 Baths ⋅ 410310 MLS ⋅ Fee Simple Tenure
Where Potential Meets Pa'ina! This Hali'imaile property is currently situated as a single-story, 3-bedroom, 1.5-bath main home plus a 1-bedroom, 1-bath studio — 4 bedrooms and 2.5 baths total, split across two living spaces(and may have nonconformities, Buyers to do their due diligence.) Ideal for multigenerational living, rental income, or simply extra room to grow into. The original aluminum roof nods to the home's plantation-era roots, while the interior has been renovated and well maintained over the years — tile, vinyl & laminate bamboo flooring, updated cabinetry, granite counters, and an open kitchen-to-dining flow. This home wears its age honestly and needs some TLC, but the bones are solid and the potential is real. Outside, a covered carport leads to a shaded, plant-filled patio, and a deck off the back opens onto a spacious yard framed by banana trees & more. From a few spots around the home, you'll catch genuine peek-a-boo ocean views — a rare bonus at this price point. A neighborhood park sits just around the corner. The biggest opportunity: the lot is zoned R-1 Residential with Urban zoning, opening the door to build up to 2 additional accessory dwelling units (buyer to verify all zoning/ADU potential with the County). 27 Paina Street is an honest home with good bones and real upside, ready for an owner to bring it to its full potential. The property is currently tenant-occupied. Do not disturb tenants. Contact your go-to Realtor for more info today! The Owner is a licensed Realtor in the State of Hawai'i.

27 Paina St, Makawao

Listing courtesy of Real Broker.

$1,199,000
4 Beds ⋅ 2 Baths ⋅ 410269 MLS ⋅ Fee Simple Tenure
Welcome to your dream home in the heart of the historic Haliimaile Plantation Village! This beautifully maintained 4-bedroom, 2-bathroom residence offers the perfect blend of Upcountry charm and incredible future potential. Step inside to discover a bright and versatile layout designed to adapt to your lifestyle. Whether you are looking for a spacious family home, an ideal setup for multigenerational living, or a savvy opportunity for potential rental income, this property accommodates it all with ease. The outdoor oasis is an absolute showstopper, boasting a fully fenced garden area that functions as a lush, edible paradise. Harvest your own fresh tropical fruit from a mature orchard featuring White Pirie Mango, Tango Mandarin, Ruby Star Grapefruit, Tahitian Lime, Dragonfruit, Purple Lilikoi, Apple Bananas, Mountain Apple, Kaffir Lime, Avocado, Papaya, and an impressive patch of 50 pineapple plants. The property also features a large chicken coop for farm-fresh eggs, a peaceful pond complete with fish and mature water plants, a wooden children's swingset, and a two-story wood play set. Whether you are relaxing on the shaded back patio or watching the kids play, this backyard is a private island sanctuary. What truly sets this property apart is an extraordinary, future-proof asset: the owners have fully approved permits in hand to build up! Skip the months of county delays and immediately expand your living space to capture breathtaking ocean and mountain views. Location! 40 Leie St places you just moments away from local favorites like the Haliimaile General Store, excellent schools, and the vibrant culture of Makawao town, all while being just a short drive down the hill to Maui’s North Shore beaches. Opportunities with this level of versatility, pre-approved growth potential, and sustainable lifestyle features rarely hit the Haliimaile market. Don’t miss your chance—contact your favorite Realtor today to schedule a private viewing!

40 Leie St, Makawao

Listing courtesy of Keller Williams Realty Maui-Ka.

$1,650,000
2 Beds ⋅ 2 Baths ⋅ 410267 MLS ⋅ Fee Simple Tenure
Follow the country road to the very top of Piiholo Road, where peaceful Upcountry living, privacy, and breathtaking surroundings await. Nestled on this exceptional 3 Acre property is a custom-crafted 2-bedroom bamboo home that blends natural beauty, sustainability, and timeless design. Bamboo is prized around the world for its strength, warmth, and renewable qualities, creating a truly unique living environment. A long ribbon driveway welcomes you to the home, where custom craftsmanship and thoughtful details create living spaces with views of the surrounding countryside and the ocean beyond. The property is well equipped with abundant potable water supplied by three 30,000-gallon water storage tanks, providing ample capacity for the home and agricultural uses. A spacious barn adds versatility, featuring a separate apartment and a large workshop currently used for woodworking. Whether you're looking for space to farm, create, work, or simply enjoy the Upcountry lifestyle, this property offers endless possibilities. An opportunity to own a private Maui property where craftsmanship, sustainability, and quiet country living come together. So peaceful!

156 Alaluana Rd, Makawao

Listing courtesy of Coldwell Banker Island Prop(P).

$999,000
2 Beds ⋅ 1 Baths ⋅ 410243 MLS ⋅ Fee Simple Tenure
Nestled on a private road, 37 Pukiki Place offers the peace, privacy, and tranquility that define Upcountry Maui living. This recently renovated single-level residence is located in one of Maui’s most sought-after microclimates, where cool trade winds, beautiful ocean and North Shore views, and a serene setting create an exceptional place to call home. Thoughtfully designed with an emphasis on indoor-outdoor living, the spacious 253 square foot covered lanai and enclosed carport provide the perfect space for entertaining, dining, or simply unwinding while enjoying the surrounding beauty. Recently CPR’d and complete with its own septic system, this move-in-ready home offers the ideal blend of comfort, functionality, and low-maintenance living. The fully fenced yard provides ample space for pets, gardening, and enjoying the Upcountry lifestyle, with room to create your own private oasis. Conveniently located just minutes from Makawao Town’s charming boutiques, local restaurants, cafés, and renowned art galleries, you’ll also appreciate easy access to Seabury Hall, Carden Academy, Montessori School of Maui, and many of the island’s top public and private schools. If you’ve been searching for the “right-sized” Upcountry home that combines privacy, convenience, breathtaking views, and a true sense of tranquility, 37 Pukiki Place delivers. This is a CPR Residential condo Unit #B.

37 Pukiki Pl Unit B, Makawao

Listing courtesy of Coldwell Banker Island Prop(S).

$1,499,000
6 Beds ⋅ 4 Baths ⋅ 410242 MLS ⋅ Fee Simple Tenure
Tucked away on a peaceful private road, 35 Pukiki Place presents a rare opportunity to enjoy the best of Upcountry Maui living in one of the island’s most desirable microclimates. Recently renovated, this expansive 6 bedroom, 4 bathroom residence captures refreshing trade winds, beautiful ocean and North Shore views, and the privacy and tranquility that make this area so special. This two-story home’s greatest asset is its remarkably versatile floor plan, thoughtfully designed to provide exceptional separation of living spaces, with separate entrances for both levels, that feels like getting two homes for the price of one. Whether accommodating multigenerational living, extended family, long-term guests, a private home office, creative studio, fitness space, or simply providing room for everyone to spread out, the possibilities are endless. Indoor and outdoor spaces blend seamlessly, creating an inviting setting for entertaining, gathering with family and friends, or enjoying peaceful mornings and cool Upcountry evenings surrounded by nature. The fenced yard offers ample room for pets, gardening, outdoor recreation, or creating your own private sanctuary. Recently CPR’d and move-in ready, this property offers flexibility rarely found in today’s market. Conveniently located just minutes from Makawao Town’s acclaimed restaurants, cafes, boutiques, and renowned art galleries, while also providing easy access to Seabury Hall, Carden Academy, Montessori School of Maui, and many of the island’s premier public and private schools. Whether you’re seeking room to grow, a flexible layout to fit your evolving lifestyle, or simply a peaceful retreat with room for everyone, 35 Pukiki Place delivers an exceptional combination of space, comfort, privacy, and convenience in one of Upcountry Maui’s most coveted locations. Experience the side of Maui where life slows down. This is a CPR Residential condo Unit #A.

35 Pukiki Pl Unit A, Makawao

Listing courtesy of Coldwell Banker Island Prop(S).

$2,288,888
3 Beds ⋅ 4 Baths ⋅ 410231 MLS ⋅ Fee Simple Tenure
Be the first to call this brand-new home, completed in 2026, your own! Located in the very sought out Kualono subdivision, this thoughtfully designed 3-bedroom, 3.5-bath residence offers 1,995 sq. ft. of modern living space on an expansive 18,208 sq. ft. lot. The flexible floor plan provides versatility to suit a variety of needs, while elegant Imperial Veneer Finish walls adds timeless character and refined craftsmanship throughout this custom home. Enjoy breathtaking mountain views of Haleakala and stunning bicoastal views from this exceptional property. With no neighbor directly behind, the home offers an added sense of openness and privacy. The landscape is ready for your personal vision, creating the opportunity to design outdoor spaces that reflect your style. Call your favorite realtor to schedule a private showing today.

94 Leiohu Cir, Makawao

Listing courtesy of Keller Williams Realty Maui-Ka.

$1,500,000
3 Beds ⋅ 2 Baths ⋅ 410189 MLS ⋅ Fee Simple Tenure
Welcome to your own private retreat! This comfortable, single-level 3-bedroom, 2-bath home sits on 2.5 level, fully fenced and gated acres, offering the perfect blend of privacy, peace, and usable outdoor space. Relax year-round on the spacious wraparound covered deck, complete with a brand-new hot tub—an ideal spot to unwind while enjoying the tranquil surroundings. The detached 2.5-car garage provides ample room for two vehicles plus extra space for storage, hobbies, or a workshop. Whether you're looking for room to garden, entertain, keep pets, or simply enjoy the serenity of country living, this property offers endless possibilities in a quiet, secluded setting. Recent survey, floor plan, and tent fumigation warranty are available in the Associated Documents.

1160 Ehu Rd, Makawao

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

$550,000
410167 MLS ⋅ Fee Simple Tenure
Perched along desirable Alaluana Road in Olinda, this exceptional vacant parcel offers breathtaking mountain and ocean views in one of Upcountry Maui's most scenic locations. The dramatic sloped topography is enhanced by several terraces, creating visual interest and providing a unique setting for a custom home designed to complement the land's natural contours. The lower portion of the property is planted with renowned Hawaiian Koa hardwood trees, adding to the property's natural beauty and Upcountry character. Enjoy cool Olinda temperatures, spectacular sunsets, and panoramic vistas stretching from the slopes of Haleakala to the coastline. Overhead electricity is available, and catchment water systems are common in the area. Conveniently located just minutes from Makawao Town while offering the peace and privacy of Upcountry living. Buyer to conduct their own due diligence regarding water, utilities, building feasibility, grading requirements, access, and all development possibilities.

Alaluana Rd, Makawao

Listing courtesy of Hawaii Life (MA).

$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).

$1,098,000
3 Beds ⋅ 2 Baths ⋅ 410138 MLS ⋅ Fee Simple Tenure
Perched just above Makawao Town, 1131 Kehau Place captures the essence of Upcountry living with sweeping ocean and West Maui Mountain views, cool trade winds, and the convenience of being just minutes from schools, restaurants, shopping, and everyday essentials. This move-in-ready home has been thoughtfully updated with remodeled bathrooms and a refreshed kitchen featuring new stainless steel appliances. Large windows and inviting living spaces frame the stunning views, creating a seamless connection between indoor comfort and Maui’s natural beauty. Situated on a 5-bedroom septic system, the property offers flexibility and future potential. The lower level provides additional space that could serve a variety of uses, including a home office, guest quarters, or future expansion possibilities. Whether you’re enjoying morning coffee while taking in the panoramic views or unwinding at sunset as the West Maui Mountains glow in the distance, this property offers the perfect blend of privacy, convenience, and the Upcountry lifestyle that so many seek. Easy to show and ready for its next chapter.

1131 Kehau Pl, Makawao

Listing courtesy of Compass-W.

$1,195,000
5 Beds ⋅ 3 Baths ⋅ 410149 MLS ⋅ Fee Simple Tenure
This super charming 5-bedroom, 2.5-bathroom home in Pukalani is set on nearly 14,000 sq.ft., the property showcases sweeping 180-degree ocean and mountain views from its expansive lanai, kitchen, and the primary bathroom's vintage tub! The generous fenced grounds—including a permitted 80-foot shed, large yard, and fruit trees—provide ample space to relax, entertain, or play, while an outdoor shower enhances the island lifestyle. A newly installed 1500-gallon septic system is a very valuable improvement for future owners on Maui! Ideally located near parks, shopping, trendy Upcountry eateries, and the popular Saturday farmers market, this timeless haven blends views, open-air living, opportunity, versatility, and location convenience. Layout and square footage may differ from tax records. Bring your vision to life! Call your realtor, easy to see!

84 Kilakila Pl, Makawao

Listing courtesy of eXp Realty.

$4,400,000
2 Beds ⋅ 3 Baths ⋅ 410147 MLS ⋅ Fee Simple Tenure
Located in Baldwin Ranch Estates, this property is a refined expression of contemporary plantation coastal design, where timeless architecture and effortless indoor-outdoor living come together against a backdrop of sweeping ocean and West Maui Mountain views. Designed by Jeff Lundahl, the residence is oriented to capture Maui's natural beauty from nearly every room, with expansive pocketing doors opening to an oversized covered lanai that becomes a seamless extension of the living space. The gated entry to resort-inspired grounds are designed for both relaxation and entertaining, featuring a sparkling pool, a pool cabana with a lounge area, a bathroom, and an outdoor shower, all surrounded by beautifully landscaped living areas that embrace Maui's year-round climate. A spacious three-bay garage of more than 1,000 square feet includes versatile air conditioned flex space and a bathroom, providing options for a home gym, workshop, creative studio, and additional storage for surfboards, bikes, and other North Shore pursuits. Positioned between the charming boutiques and cafés of Makawao and the vibrant beaches and lifestyle of Paia, this exceptional property has refreshing trade winds, panoramic vistas, and convenient access to some of Maui's most sought-after schools, world-class beaches and connections to Maui's North Shore lifestyle. The is Unit B of a CPR.

2350 Baldwin Ave Unit B, Makawao

Listing courtesy of Hawaii Life (W).

$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.

$2,395,000
11 Beds ⋅ 8 Baths ⋅ 409725 MLS ⋅ Fee Simple Tenure
Also listed under Residential MLS #409724. This unique multi-structure, multi-unit property 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 4 separate structures with a total of 8 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.

$1,895,950
3 Beds ⋅ 3 Baths ⋅ 409975 MLS ⋅ Fee Simple Tenure
LUXURY UPSCALE Home in KULAMALU HILLTOP GATED COMMUNITY Available for purchase is this beautifully updated custom home located in the highly sought-after Kulamalu Hilltop neighborhood in Lower Kula. Tucked within a private gated enclave of only 12 custom residences, this exceptional home offers the perfect balance of Upcountry tranquility and everyday convenience. Enjoy walking distance to the popular Saturday Upcountry Farmers Market, restaurants, shops, and services, while maintaining quick access to schools (Seabury, Carden, Kamehameha, King Kekaulike, Waldorf), Kahului, and the rest of Maui. Inside, the spacious open-concept floor plan is filled with natural light and thoughtfully updated with designer finishes throughout. Recent improvements include a stunning remodeled fireplace, custom windows and trim, upgraded lighting, AC throughout, and modern fixtures that create a warm island aesthetic. The gourmet kitchen features extensive cabinetry, a large island, and seamless flow into the dining and living spaces—perfect for entertaining or everyday family living. The oversized primary master suite offers a peaceful retreat with abundant natural light and elegant finishes. Property Highlights: • Approximately 2,800 sq ft • Oversized two car garage • 3 Bedrooms, 2.5 Bathrooms • Private gated community with only 12 homes • Spacious open-concept floor plan • Remodeled designer fireplace feature wall • Custom windows, trim, and upgraded lighting • Split-system air conditioning • Gourmet kitchen with oversized island • Beautiful primary suite • Professionally landscaped fully fenced yard • Walking distance to Kulamalu Farmers Market • Convenient access to schools, shopping, dining, and the highway This is a rare opportunity to enjoy one of Upcountry Maui's most desirable neighborhoods in a thoughtfully upgraded custom home.

32 Ohia Lehua Pl, Makawao

Listing courtesy of Hawaii Life (W).

$875,000
409974 MLS ⋅ Fee Simple Tenure
Rare opportunity to own one of the only vacant land offerings in Lower Olinda. Ideally located just 5 Mins from charming Makawao Town, this exceptional 2-acre parcel offers the perfect blend of Upcountry serenity, convenience, and ocean views. Approximately 1 acre has been recently cleared, creating easy access to several prime building sites and allowing you to fully appreciate the property's potential. Whether you envision a custom home, private estate, or peaceful retreat, the groundwork has already begun. A water meter is installed, adding significant value and convenience for future development. Unlike many properties in the area, this is not a CPR'd parcel, offering greater privacy and the opportunity to enjoy the full benefits of owning a standalone property. Surrounded by the beauty of Upcountry Maui, this parcel combines open space, cool temperatures, and stunning vistas in one of the island's most desirable locations. With very limited vacant land available in Olinda, this is a rare chance to create your dream home in a truly special setting. BUILD-FARM-LIVE. One Seller holds an Inactive Hawaii Real Estate License

Olinda Rd, Makawao

Listing courtesy of Compass-W.

$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.

$989,000
3 Beds ⋅ 2 Baths ⋅ 409804 MLS ⋅ Fee Simple Tenure
Perched in coveted Upcountry Maui, this original Plantation-style 3-bedroom home captures breathtaking north and south shore views, sweeping across the entire Central Valley to the majestic West Maui Mountains. Large picture windows in the living room take in the huge view as does the kitchen window. A full bath adjoins the bedrooms while a half bath completes the laundry room. An enclosed patio opens up with patio doors to the living room and the large 2 car garage and work area. Rich with timeless charm and character, this property offers an incredible opportunity to restore and create one of the area's most desirable residences. Set up high on a spacious lot, the property features a magnificent mature monkeypod tree, expansive outdoor space, and endless potential for indoor-outdoor island living. With R-3 zoning, there is also the added possibility of constructing an additional dwelling, making this an exceptional investment or multigenerational opportunity. Bring your vision and transform this special property into a true Upcountry gem — where stunning views, classic Hawaiian charm, and future potential come together in one remarkable setting.

2840 Koea Pl, Makawao

Listing courtesy of Corcoran Pacific Properties.

$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).

$968,000
3 Beds ⋅ 2 Baths ⋅ 409182 MLS ⋅ Fee Simple Tenure
Incredible Value in Makawao! Discover the charm of Upcountry living in this maintained single-level home, ideally situated on a quiet cul-de-sac in one of Makawao's most desirable neighborhoods. Filled with natural light and refreshing cross breezes, this inviting 3-bedroom, 2-bath home features vaulted ceilings, owned photovoltaic panels, solar hot water, wood flooring, and a functional layout designed for comfortable island living. The spacious yard is perfect for entertaining, gardening, or creating your own outdoor retreat. The two-car garage features high open ceilings, providing excellent storage and exciting potential for additional living space, adding flexibility to fit your future needs. Conveniently located just minutes from charming Makawao Town, Eddie Tam Park, schools, shopping, and local dining, and only about 15 minutes from Kahului and Maui's beautiful beaches, this home offers the ideal blend of Upcountry charm and everyday convenience. With exceptional value in one of Maui's most sought-after communities, this is an opportunity you won't want to miss. Schedule your private showing today!

1088 Mamalu Pl, Makawao

Listing courtesy of Compass.

$799,000
409002 MLS ⋅ Fee Simple Tenure
Looking to build Upcountry? 11 Huliamahi Place offers a compelling combination of location, views, and usability. This B unit of a two-unit CPR offers an acre of gently sloped land, views of the ocean, Haleakala, and the West Maui Mountains, and entitlements to build a cottage of up to 1,500 square feet. There is plenty of space to build your home, grow a garden, and plant an orchard. Private water and underground utilities run to the land. There is a storage container for you to keep gardening tools, and building supplies before you build. The location is hard to beat for convenience and climate. It is just minutes away from Kulamalu. There you will find the Saturday Upcountry Farmer’s market, food trucks, Longs Drugs, Farm to Table food at Marlow, organic produce at Okoa Farms Store, and libations at the Lahaina Brewing Company. Other Upcountry restaurants, shops, and amenities are close by in Pukalani and Makawao Town. Central Maui and North Shore Beaches are just 15 minutes away. If you are interested in building your home and life Upcountry, contact your favorite Realtor to arrange a showing.

11 Huliamahi Pl Unit Unit B, Makawao

Listing courtesy of The Maui Real Estate Team Inc.

$1,150,000
3 Beds ⋅ 2 Baths ⋅ 408939 MLS ⋅ Fee Simple Tenure
Your whole family will have space in this energy efficient, turnkey, Bungalow Style, multi-level "Mini Mansion" It's nestled Upcountry on Haleakala. Walking distance to schools and Historical Makawao Town and short drive to town, beaches, and airport. 3 bedroom 2 baths can be divided into a separate 1 bd 1 ba attached ohana with private yard, kitchen, driveway, and entrance that easily could be rented. A new perimeter fence has created 5 enclosed unique yards. Living on a private road is safe for kids and pets. Extra large, tall carport with a workshop and observation deck on top with an incredible view creates one of the best spaces on the property. Pictures don't do it justice I'm able to email more detailed pictures I look forward to hearing from you. All comments, data is provided by seller or seller's representatives. Buyer to confirm all & hold all parties harmless from any discrepancy data in the mls and advertising. Limited Service–Data Entry Addendum signed by seller/s must be signed by buyer/s with Purchase Contract.

3586 Kalua Pl, Makawao

Listing courtesy of Nathalie Mullinix Rlty Universal Inc.

$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.

$1,399,000
3 Beds ⋅ 2 Baths ⋅ 408348 MLS ⋅ Fee Simple Tenure
Bring your vision to this peaceful Upcountry property nestled just below the cool cloud line of Upper Piiholo. Set on two (2) beautifully established acres, this three (3) bedroom two (2) bath home offers more than twenty six hundred (2600+) square feet of interior space along with views that create an inspiring backdrop for a thoughtful renovation. Native trees, tall pines, and fragrant eucalyptus surround this property, offering both privacy and a deep connection to the land. The home is ready for someone who appreciates character and craftsmanship and wants to restore it to its original charm. A generous wraparound deck already frames the exterior, inviting a seamless indoor and outdoor lifestyle. Inside, the main level features an open living, dining and kitchen area with vaulted ceilings and a striking stone accented fireplace. Two (2) bedrooms and a full bath completes this floor. The primary suite rests on the upper level, offering treetop views and natural light. The finished basement offers a one (1) car parking garage and a large room, perfect for a home office, home theatre or possibly a work out/yoga studio. With internet available and plenty of room to reimagine both indoor and outdoor spaces, this property is a rare opportunity to create something truly special. Whether you update the existing layout or transform it into a more modern Upcountry retreat, the setting and foundation are already in place. This much loved home is waiting for its next chapter.

2400 Piiholo Rd, Makawao

Listing courtesy of Coldwell Banker Island Prop(Ka).

$4,037,500
408107 MLS ⋅ Fee Simple Tenure
** Sale includes MLS #s 408092, 408093, 408094, 408095, 408096, 408097, 408098, 408099, 408100, 408101, 408143, 408102, 408103, 408104, 408106 & 408107 ** Rare opportunity to acquire a multi-site land portfolio spanning Wailuku, Kihei, and Makawao—three of Maui’s most sought-after and growing regions. The portfolio consists of 16 parcels totaling approximately 272.055 acres, offering significant scale, diverse topography, and strategic locations suitable for investment, master planning, or phased development. Properties are offered for sale exclusively as a single portfolio. Any individual parcel pricing shown is for MLS compliance purposes only and does not reflect standalone availability or value. The portfolio purchase price is $48,000,000.00

Makani Rd, Makawao

Listing courtesy of Commercial Prop of Maui LLC.