Makawao/Olinda/Haliimaile Real Estate

Welcome to the enchanting neighborhoods of Makawao, Olinda, and Haliimaile, nestled in the lush hills of Maui, Hawaii. These charming communities offer a unique blend of rich history, vibrant culture, and stunning natural beauty, making them a hidden gem for those seeking a tranquil lifestyle in paradise.

Makawao, often referred to as the “Paniolo (cowboy) town,” is steeped in a rich ranching heritage. Stroll through its picturesque streets lined with art galleries, quaint shops, and local eateries that serve up mouthwatering Hawaiian cuisine. The community is known for its welcoming spirit and hosts various events throughout the year, including the famous Makawao Rodeo, where you can witness thrilling cowboy competitions and experience the island's ranching culture firsthand.

Just a short drive away, Olinda offers breathtaking views of the island and is renowned for its cool, crisp climate. This peaceful neighborhood is perfect for those who appreciate nature, with lush forests and hiking trails that lead to stunning vistas. The area is also home to several farms, where you can find fresh produce and artisanal goods that reflect the island's agricultural heritage.

Haliimaile, a quaint community nestled between Makawao and Upcountry Maui, is known for its rich pineapple history and laid-back atmosphere. The Haliimaile Distilling Company offers a unique taste of local spirits, showcasing the flavors of Maui in every sip.

Together, these neighborhoods create a harmonious blend of culture, community, and natural beauty. Whether you’re looking to settle down or simply exploring, Makawao, Olinda, and Haliimaile promise a lifestyle that is as vibrant as it is serene. Come and discover your slice of paradise in these enchanting Upcountry Maui communities!

Newest Listings in Makawao/Olinda/Haliimaile

156 Alaluana Rd, Makawao $1,650,000

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...

ACTIVE Status
2 Beds
2 Baths
410267 MLS
Fee Simple Tenure

Courtesy of Coldwell Banker Island Prop(P)

Listing courtesy of Coldwell Banker Island Prop(P).

37 Pukiki Pl Unit B, Makawao $999,000

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...

ACTIVE Status
2 Beds
1 Baths
410243 MLS
Fee Simple Tenure

Courtesy of Coldwell Banker Island Prop(S)

Listing courtesy of Coldwell Banker Island Prop(S).

35 Pukiki Pl Unit A, Makawao $1,499,000

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 micro...

ACTIVE Status
6 Beds
4 Baths
410242 MLS
Fee Simple Tenure

Courtesy of Coldwell Banker Island Prop(S)

Listing courtesy of Coldwell Banker Island Prop(S).

94 Leiohu Cir, Makawao $2,288,888

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 ...

ACTIVE Status
3 Beds
4 Baths
410231 MLS
Fee Simple Tenure

Courtesy of Keller Williams Realty Maui-Ka

Listing courtesy of Keller Williams Realty Maui-Ka.

Alaluana Rd, Makawao $550,000

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 locati...

ACTIVE Status
410167 MLS
Fee Simple Tenure

Courtesy of Hawaii Life (MA)

Listing courtesy of Hawaii Life (MA).

1740 Piiholo Rd, Makawao $2,649,000

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 tim...

ACTIVE Status
5 Beds
4 Baths
410159 MLS
Fee Simple Tenure

Courtesy of Coldwell Banker Island Prop(S)

Listing courtesy of Coldwell Banker Island Prop(S).

1131 Kehau Pl, Makawao $1,098,000

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 con...

ACTIVE Status
3 Beds
2 Baths
410138 MLS
Fee Simple Tenure

Courtesy of Compass-W

Listing courtesy of Compass-W.

15 Olinda Rd, Makawao $2,395,000

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 an...

ACTIVE Status
5 Beds
4 Baths
409724 MLS
Fee Simple Tenure

Courtesy of eXp Realty

Listing courtesy of eXp Realty.

15 Olinda Rd, Makawao $2,395,000

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-ter...

ACTIVE Status
11 Beds
8 Baths
409725 MLS
Fee Simple Tenure

Courtesy of eXp Realty

Listing courtesy of eXp Realty.

2840 Koea Pl, Makawao $989,000 ▼

Perched in coveted Upcountry Maui, this original Plantation-style 3-bedroom home captures breathtaking north and south shore views, sweeping across the entire Central Val...

ACTIVE Status
3 Beds
2 Baths
409804 MLS
Fee Simple Tenure

Courtesy of Corcoran Pacific Properties

Listing courtesy of Corcoran Pacific Properties.

1088 Mamalu Pl, Makawao $968,000 ▼

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 ...

ACTIVE Status
3 Beds
2 Baths
409182 MLS
Fee Simple Tenure

Courtesy of Compass

Listing courtesy of Compass.

11 Huliamahi Pl Unit Unit B, Makawao image

11 Huliamahi Pl Unit Unit B, Makawao $799,000

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 s...