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

170 Kee Rd, Makawao
$3,200,000
3 Beds ⋅ 2 Baths ⋅ 411288 MLS ⋅ Fee Simple Tenure
Welcome to 170 Kee Road, a beautiful, versatile, and private 4.3-acre estate, nestled on a quiet country road at the fresh elevation of 1,600 feet, just a half mile from Makawao town. With two separate entrances, multiple structures, mature trees, a unique zoning, and a ¾" water meter, the property offers a multitude of possibilities. The paved main entrance ascends to a charming 3-bedroom 2-bath cottage, set against a neighboring pasture. The 2017 custom-built cottage enjoys a leeward lanai, private lawn area, separate electric meter, septic system, and ample parking. The Royal Palm-lined driveway continues past mature fruit trees, two flexible-use structures, and the former tack building with lanai and enclosed garage, to the current main home backing to a private pasture with unobstructed Haleakala views. The mowed and maintained pasture is framed by forest and organic fruit trees with a rain water filled water tank for landscaping. Comfortably separated from the other structures, the quaint 3-bedroom 2-bath home was fully renovated in 2018 and features high ceilings, quartz countertops, owned grid tied PV system and a spacious lanai that overlooks the pasture, small gulch, fruit trees with stunning mountain views. In this special setting, morning songbirds and nene geese are frequently seen and heard overhead. With Buyer's due diligence, some possibilities to explore: building an additional dwelling, CPR, re-creating an equestrian estate, multigenerational living and much more! At idyllic, yet convenient 170 Kee Road, envision and create a unique lifestyle of your own. Please see the plot map locating structures and a list of fruit trees on the property in the MLS Documents.

170 Kee Rd, Makawao

Listing courtesy of REMAX Hawaii Maui.

85 Ulana St, Makawao
$1,700,000
5 Beds ⋅ 3 Baths ⋅ 411184 MLS ⋅ Fee Simple Tenure
Welcome to 85 Ulana Street, a versatile Upcountry property located in the desirable Maui Uplands neighborhood of Makawao. Situated in a peaceful residential setting, the property features a spacious 5-bedroom, 3-bath main residence along with a detached 2-bedroom, 1-bath cottage, offering excellent flexibility for extended family, guests, a home office, or rental income. Mature landscaping and the generous outdoor space create a private Upcountry atmosphere with room to enjoy Maui’s year-round indoor-outdoor lifestyle. Maui Uplands is conveniently located between Makawao and Pukalani, providing easy access to schools, shopping, restaurants, and everyday conveniences while maintaining the quiet residential feel Upcountry is known for. Community amenities include a swimming pool, tennis court, and clubhouse. With a main residence and detached cottage, 85 Ulana Street presents a unique opportunity for those looking for additional living space, rental potential, or a flexible multi-generational property in one of Makawao’s established neighborhoods.

85 Ulana St, Makawao

Listing courtesy of Commercial Prop of Maui LLC.

1018 Ulele St Unit Unit B, Makawao
$744,000
2 Beds ⋅ 1 Baths ⋅ 411070 MLS ⋅ Fee Simple Tenure
Upcountry Cottage with Ocean Views & Open Yard This freestanding 2-bedroom, 1-bath cottage offers approximately 600 sq. ft. of living space and was renovated in 2023. The bright, open-concept kitchen and living area creates a welcoming atmosphere, with partial ocean views from both spaces. Updated vinyl flooring, kitchen appliances purchased in 2025, and a washer and dryer purchased in 2026 add to the home’s appeal. Enjoy the added convenience of a 200 sq. ft. carport, providing covered outdoor space, along with an open yard offering room to enjoy the fresh Upcountry air. Located just minutes from Makawao town’s shopping, dining, schools, and parks, this move-in-ready cottage combines everyday convenience with the cooler climate and relaxed lifestyle of Upcountry Maui. This is Unit B of a two-unit CPR. Don’t miss your chance to make this exceptional property your own—schedule a showing today!

1018 Ulele St Unit Unit B, Makawao

Listing courtesy of Keller Williams Realty Maui-Ka.

93 Piiholo Rd Unit B, Makawao
$725,000
411068 MLS ⋅ Fee Simple Tenure
This is a Residential Condo Property, Unit B of the Piiholo Meadows Condominium, and is approved for a cottage (farm dwelling of up to 1,500 square feet of living area). Ocean views stretch across Maui’s North Shore to the island of Molokai from these 3.550 acres of open Upcountry pasture on Piiholo Road in Makawao. The property offers convenient access, a manageable footprint, and views of the West Maui Mountains across the isthmus, making it well suited to a farm cottage, a garden-focused homestead, or a peaceful Upcountry retreat. Mornings here are cool and green, and evenings bring sunset light over the ocean and quiet. Makawao town is just minutes away, with galleries, boutiques, cafes, paniolo heritage, the Hui No’eau Visual Arts Center, and the local favorite, Komoda Bakery. Kahului, the airport, and Paia's beaches are an easy drive. Recorded subdivision CC&Rs include protected ocean-view corridors and architectural review, which help preserve the neighborhood’s character and views. There are no monthly HOA dues. The Piiholo area receives consistent Upcountry rainfall, making rainwater catchment a practical and widely used option. Agricultural zoning.

93 Piiholo Rd Unit B, Makawao

Listing courtesy of Compass-W.

93 Piiholo Rd Unit A, Makawao
$1,025,000
411067 MLS ⋅ Fee Simple Tenure
This is a Residential Condo Property, Unit A of the Piiholo Meadows Condominium, and is approved for the main house. Sweeping North Shore ocean views define this 12.007-acre property of rolling Upcountry pasture at the end of a quiet stretch of Piiholo Road in Makawao. From the main home site, the Pacific stretches across Maui’s North Shore to the island of Molokai on the horizon, with the West Maui Mountains across the isthmus. Turn around, and a lush, forested gulch wraps the back of the property, adding green views and natural privacy. A trail leads down from the pasture into scenic Maliko Gulch, whose streambed flows seasonally after Upcountry rains, a memorable walk right from your own land. Up top, roughly six and a half acres of open, usable pasture are ready for a home site, gardens, orchards, or horses. This is Upcountry living at its best: cool mornings, green hillsides, and ocean views that stretch for miles, yet only minutes from Makawao town, with its galleries, boutiques, cafes, the Hui No’eau Visual Arts Center, and the famous cream puffs at Komoda Bakery. Kahului, the airport, and the North Shore beaches of Paia are an easy drive. Recorded subdivision CC&Rs include protected ocean-view corridors and architectural review, which help preserve the neighborhood’s character and views. There are no monthly HOA dues. The Piiholo area receives consistent Upcountry rainfall, making rainwater catchment a practical and widely used option.

93 Piiholo Rd Unit A, Makawao

Listing courtesy of Compass-W.

1160 Ehu Rd, Makawao
$1,500,000
3 Beds ⋅ 2 Baths ⋅ 411002 MLS ⋅ Fee Simple Tenure
Enjoy the space, privacy and cooler climate of Upcountry living in this single-level 3-bedroom, 2-bath home set on 2.5 level, usable acres. High vaulted ceilings create an open, airy feel, while a wrap-around covered deck extends the living space outdoors and provides a comfortable setting to enjoy the peaceful surroundings. The fully fenced and gated property features an expansive green lawn with plenty of room to enjoy the acreage. A detached 2.5-car garage offers space for two vehicles plus a workshop, storage or hobby area. Privately situated yet easy to show, this Upcountry property combines comfortable single-level living with generous usable land and versatile outdoor space. Photos have been virtually staged. This is not a CPR. Zoning allows for 1 main house, a 2nd dwelling of up to 1,500 sf. (permitting conditions apply).

1160 Ehu Rd, Makawao

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

11 Huliamahi Pl Unit Unit B, Makawao
$750,000
411001 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.

143 Leiohu Cir, Makawao
$2,641,000
3 Beds ⋅ 3 Baths ⋅ 410991 MLS ⋅ Fee Simple Tenure
Enjoy cool upcountry breezes, bicoastal views and the convenience of nearby Makawao Town in this thoughtfully upgraded ranch style residence. Situated in a gated community on a peaceful cul-de-sac, this home showcases quality upgrades and timeless finishes throughout including; cherry wood cabinetry, soft close drawers, gas cooktop, double ovens, new dishwasher and quartz countertops blending warmth and functionality. The home includes a gas fireplace, gas tankless water heater, 15 PV panels (leased, transferable to qualified buyer) and a Tesla charger delivering modern performance with island practicality. The outdoor space is equally inviting with established grapefruit, lemon and avocado trees. A beautiful home being offered furnished (with a separate bill of sale) , bring your personal touch and make 143 Lei‘ohu Circle your Maui Dream Home.

143 Leiohu Cir, Makawao

Listing courtesy of Keller Williams Realty Maui-Ki.

189 Hokupa St Unit Lot 36, Makawao
$1,525,000
4 Beds ⋅ 3 Baths ⋅ 410946 MLS ⋅ Fee Simple Tenure
Discover Hoku’ula in the charming town of Haliimaile, set on the mild slopes of Haleakala and overlooking Maui’s famous North Shore. Construction is underway, with an estimated completion date of November 2026. Expansive ocean and mountain views will greet you from this bottom row, two-story C floor plan home with 4 bedrooms and 2.5 bathrooms. Features include; 9 foot ceilings, open layout, covered lanai, and an attached two car garage. Notable amenities include; split air-condition, rain gutters, stainless-steel appliances, double paned windows, soft close cabinetry, upgraded carpet, upgraded LVP flooring, Kohler tubs, sinks and toilets. Located just minutes from Kahului’s modern conveniences and the quiet appeal of Paia and Makawao. This is truly a unique opportunity to own your piece of paradise on Maui, a wonderful place to call home. All renderings and floor plans are conceptual and are not intended to be an actual depiction of the home, driveway, or landscaping. Square footage and room sizes are approximate. Buyer and Buyer's Agent to conduct due diligence.

189 Hokupa St Unit Lot 36, Makawao

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

1199 Freitas Pl Pl, Makawao
$1,200,000
3 Beds ⋅ 2 Baths ⋅ 410916 MLS ⋅ Fee Simple Tenure
Up country living at its best downtown Makawao. Lightfilled 3 bed, 2 bath one story home, new vinyl windows throughout. Expansive living room that moves into a large entertainment room, & an additional room that leads to the covered patio. Enjoy the large fenced lot filled with an abundance of fruit trees, established hedge for privacy, & roomy tool shed. The main bath has been beautifully remodeled with custom tile, counter top, & storage. Kitchen boasts new countertops & tile backsplash. The original kitchen sink stainless steel with side boards, not to be missed. Huge 2 car garage with storage, laundry room & bath with furo. Detached cottage is approx. 660 st. ft with its own electric meter and carport. A blank canvas for you to make it your own. Easy to show. This location is close to the Makawao rest., shops, entertainment, famous Komoda Bakery, schools, gyms, and other amenities.

1199 Freitas Pl Pl, Makawao

Listing courtesy of Chris Bakeman Realty LLC.

640 Makawao Ave, Makawao
$1,549,000
4 Beds ⋅ 2 Baths ⋅ 410773 MLS ⋅ Fee Simple Tenure
Over two acres on Makawao Avenue, held by the same owners for generations. The property sits up on a rise in the band between Pukalani and Makawao, with Haleakala above it and open sky in every direction. Cool mornings, usable ground, and a location that needs no explaining to anyone who knows upcountry. The parcel is zoned agricultural and largely open. Room for pasture, orchard, gardens, animals, or equipment, with space left over. A 4 bedroom, 2 bath home sits on the property and is ready to live in now. Makawao town and the shops and restaurants along Baldwin Avenue are minutes away, with Kahului a short drive down the hill. Over two acres fronting Makawao Avenue rarely becomes available, and property held this long tends to sell once and stay put. Come see it in person, since the size and the setting read differently on the ground than they do in photos. Contact your agent to schedule a private showing.

640 Makawao Ave, Makawao

Listing courtesy of Keller Williams Realty Maui-Ka.

1102 Mailuna Pl, Makawao
$1,475,000
3 Beds ⋅ 3 Baths ⋅ 410602 MLS ⋅ Fee Simple Tenure
Tucked privately at the top of a cul-de-sac, this beautifully appointed 3-bedroom, 3-bath home plus office is a Makawao residence that offers a rare combination of thoughtful design, lush surroundings, private pool, intimate outdoor spaces, and an exceptionally flexible floor plan. The home feels both gracious and wonderfully easy to live in, with a sense of privacy and tranquillity that is increasingly difficult to find. Upstairs, an inviting living room is warmed by a cozy gas fireplace, while expansive windows draw in abundant natural light and frame the verdant surroundings. The kitchen and living spaces open naturally toward the home's vine-draped lanai on the lee side- the Owner's favorite place to gather, dine, and enjoy the sweet views toward Makawao sunsets. The spacious primary suite offers a private retreat, complete with built-in bookshelves and a serene sense of separation from the rest of the home. Downstairs feels like its own private world. Two additional bedrooms and an exceptionally generous second living room create a versatile configuration for guests, extended family, a home office, or live-in relatives. From the bedrooms, step directly onto your private lanai and toward the pool and gardens, creating an effortless connection to the outdoors. Outside, the beautifully landscaped grounds are designed for privacy and enjoyment. A fabulous intimate lap pool and cozy pool pavilion provides a peaceful focal point for this residence. For energy efficiency, the property is also equipped with 32 photovoltaic panels. The location is equally compelling. Enjoy the charm of Makawao town within walking distance, while Kahului and Baldwin Beach are approximately 20 minutes away. Here, thoughtful architecture, lush grounds, privacy, flexible living spaces, and an enviable Upcountry setting come together in a truly special property. A distinctive home with wonderful possibilities.

1102 Mailuna Pl, Makawao

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

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