Makawao/Olinda/Haliimaile Real Estate

Makawao/Olinda/Haliimaile Real Estate

Makawao/Olinda/Haliimaile: A Hidden Gem in Maui, Hawaii

Nestled in the heart of Maui, Hawaii, the district of Makawao/Olinda/Haliimaile offers a unique blend of natural beauty, cultural heritage, and small-town charm. Located in the county of Maui and the city of Makawao, this region is a hidden gem waiting to be explored.

Makawao, often referred to as the "cowboy town" of Maui, is known for its rich history in ranching and paniolo (Hawaiian cowboy) culture. The town's quaint streets are lined with charming boutiques, art galleries, and local eateries, offering visitors a taste of the island's unique arts and culinary scene. Makawao also hosts the annual Makawao Rodeo, a beloved event that celebrates the area's cowboy heritage.

Olinda, located just above Makawao, is a picturesque upcountry area that offers stunning panoramic views of the island. With its cooler climate and lush greenery, Olinda is a paradise for nature lovers and hikers. The region is home to the Waihou Spring Forest Reserve, where visitors can explore hiking trails and immerse themselves in the beauty of Maui's native flora and fauna.

Haliimaile, situated to the east of Makawao, is a former plantation town that has transformed into a vibrant community. Here, you'll find the renowned Haliimaile General Store, a popular restaurant that showcases the flavors of Hawaii using fresh, locally sourced ingredients. Haliimaile is also home to the MauiWine vineyard, where visitors can indulge in wine tastings and learn about the island's winemaking history.

Whether you're seeking a peaceful retreat, an adventure in nature, or a taste of authentic Hawaiian culture, the Makawao/Olinda/Haliimaile district has it all. With its idyllic landscapes, rich heritage, and warm aloha spirit, this hidden gem in Maui, Hawaii, is waiting to be discovered.

Newest Listings in Makawao/Olinda/Haliimaile

$1,239,000
3 Beds ⋅ 3 Baths ⋅ 410434 MLS ⋅ Fee Simple Tenure
Set atop a quarter-acre lot across from the 12th fairway in Pukalani Terrace, 185 Hololani Street offers the rare combination of move-in-ready comfort and future potential. The home features 3 bedrooms, 2.5 baths, plus a versatile bonus room ideal as a dedicated office or fourth bedroom, abundant storage, a separate storage room or workshop, and two carports with covered parking for up to three vehicles. A rare private sewer connection enhances the property's long-term flexibility, allowing you to fully enjoy and maximize the land without the constraints of a cesspool or septic system. Whether you envision a future cottage or ADU, expanded living space, or simply the luxury of a generous yard, the possibilities are yours to explore (subject to County approval). Just minutes from Pukalani Country Club, shopping, parks, historic Makawao town, Kulamalu Town Center & food trucks, and some of Maui's most distinguished private schools, this is Upcountry living with room to imagine more.

185 Hololani St, Makawao

Listing courtesy of Coldwell Banker Island Prop(S).

$1,099,000
3 Beds ⋅ 3 Baths ⋅ 410426 MLS ⋅ Fee Simple Tenure
This property is the Main house of a residential CPR. Built in 2021, this beautifully maintained 3-bedroom, 2.5-bath home offers the perfect blend of modern comfort and Upcountry convenience. Ideally situated in Pukalani with easy access to Haleakala Highway. The thoughtfully designed floor plan features bright, open living spaces, contemporary finishes, and a well-appointed kitchen with stainless steel appliances, creating a welcoming atmosphere for everyday living and entertaining. Step outside to a spacious yard with plenty of room for children, furry family members, gardening, or weekend gatherings. Additional highlights include a spacious two-car garage with a dedicated 220-volt outlet, making it ready for electric vehicle charging, along with ample room for storage and outdoor gear. A solar hot water system adds to the home’s energy-efficient features. Conveniently located near some of Upcountry Maui’s highly regarded schools, parks, shopping, dining, and recreational opportunities, this move-in-ready home offers quality construction, modern amenities, and the relaxed Upcountry lifestyle you’ve been searching for.

136 Tam Yau Pl Unit 12H, Makawao

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

$1,500,000
2 Beds ⋅ 2 Baths ⋅ 410416 MLS ⋅ Fee Simple Tenure
Secluded at the top of Olinda and surrounded by state forest, 115 Alaluana Road offers privacy and profound quiet above Makawao town. Set on 1.4 agricultural acres, this classic Frank Stiller pole home reflects decades of island living through its natural, lived-in character. The two-bedroom, two-bath residence spans 2,113 square feet across two connected, single-level living spaces. Vaulted open-beam ceilings, skylights, and broad windows draw sunlight and greenery indoors, while twin lofts add versatility. The flexible floor plan offers separate great rooms, each with a wood-burning stove, for hosting, working, or creative pursuits. An open-air entry courtyard welcomes you home, while wraparound decks invite outdoor living. The back lanai sets the stage for morning coffee, relaxed meals, sunset gatherings, and stargazing. Beyond the home, an open lawn and a blue-rock retaining wall define the outdoor space, while a 600-square-foot greenhouse with garden beds offers room for growing and hands-on projects. Beneath the main living area, 1,250 covered square feet provide workspace and storage, complemented by an outdoor shower. 115 Alaluana is a unique Upcountry retreat—offering adaptable living spaces, abundant room to work and create, and an intimate connection to nature for those seeking solitude.

115 Alaluana Rd, Makawao

Listing courtesy of Compass-W.

$1,100,000
410399 MLS ⋅ Fee Simple Tenure
One of the most turnkey development opportunities in Upcountry Maui. This 1.8-acre vacant lot comes with its own three rare 5/8" county water meters and county-approved building plans for a main house with an attached ohana ready to break ground. Skip the years of waiting for the county, architectural fees, and uncertainty. Lot A is zoned R-3, which allows for a total of three homes of any size to be built. On level to gently sloping topography, the site offers sweeping views of the North Shore, Haleakala, and the West Maui Mountains. Tucked at the end of a quiet road, you get the peace of a private country setting while still being walking distance to the shops, restaurants, and charm of historic Makawao Town. Baldwin Beach is 10 minutes down the hill, and Costco and the airport are about 20 minutes away. At nearly 1,500 feet elevation, the weather is consistently cool and comfortable. Three water meters. R-3 zoning on nearly two acres. Approved plans in hand. Unit A of a 5.68 acre 3-unit CPR. The hidden gem you've been looking for!

281 Maha Rd Unit Unit A, Makawao

Listing courtesy of Coldwell Banker Island Prop-Ku.

$1,420,000
4 Beds ⋅ 4 Baths ⋅ 410393 MLS ⋅ Fee Simple Tenure
In the Hawaiian language, Iini means "to desire, yearn for, or long for"—a fitting introduction to this tastefully renovated 4-bedroom, 3.5-bath home with a new shingle roof conveniently located in Makawao. The well-designed floor plan places the spacious living and dining areas at the center of the home, separating two bedrooms on each side to provide both privacy and functionality. The remodeled kitchen features custom cabinetry, a gas range, and a convenient pass-through window to the outdoor dining area, making entertaining a breeze. This versatile space can also serve as a covered carport when desired. Recent upgrades include luxury vinyl plank flooring, split A/C throughout, instant water heater shared by primary bath and 2nd bedroom bath, and numerous thoughtful updates throughout. Beyond the dining area, the covered pavilion and expansive interlocking deck tile patio create an inviting outdoor retreat with plenty of room for relaxing, entertaining, or enjoying Makawao's comfortable Upcountry climate. 305 Iini Way—a home you'll be longing to come home to.

305 Iini Way, Makawao

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

$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).

$1,350,000
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).

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