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

640 Makawao Ave, Makawao $1,599,000

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 i...

ACTIVE Status
4 Beds
2 Baths
410773 MLS
Fee Simple Tenure

Courtesy of Keller Williams Realty Maui-Ka

Listing courtesy of Keller Williams Realty Maui-Ka.

284 Alalani St, Makawao $1,150,000

Discover the possibilities with this captivating 2-bedroom, 1-bathroom cottage situated on a little over half an acre of flat, fully usable land. Built in 2013, this well...

ACTIVE Status
2 Beds
1 Baths
410747 MLS
Fee Simple Tenure

Courtesy of Shore To Shore Realty, Inc.

Listing courtesy of Shore To Shore Realty, Inc..

742 Kekona Pl, Makawao $1,100,000

Welcome home to 742 Kekona Place, tucked into the heart of Makawao. If you love the charm of country living, the sense of community that comes with a small town, & the co...

ACTIVE Status
3 Beds
2 Baths
410627 MLS
Fee Simple Tenure

Courtesy of Coldwell Banker Island Prop-Ku

Listing courtesy of Coldwell Banker Island Prop-Ku.

1102 Mailuna Pl, Makawao $1,569,500

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 thoug...

ACTIVE Status
3 Beds
3 Baths
410602 MLS
Fee Simple Tenure

Courtesy of Equity One Real Estate Inc (P)

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

30 Pahaa Pl, Makawao $1,145,000 ▼

Welcome to 30 Paha‘a Place, a beautifully updated and exceptionally versatile Upcountry Maui home tucked away on a flag lot at the end of a quiet cul-de-sac in Pukalani. ...

ACTIVE Status
4 Beds
3 Baths
410550 MLS
Fee Simple Tenure

Courtesy of Keller Williams Realty Maui-Ka

Listing courtesy of Keller Williams Realty Maui-Ka.

3566 Kalua Pl, Makawao $835,000 ▼

Warm 4-bedroom, 2-bath home in the heart of Makawao! Conveniently located within walking distance to schools, parks, shopping, and local restaurants, this property offers...

ACTIVE Status
4 Beds
2 Baths
410447 MLS
Fee Simple Tenure

Courtesy of Tri-Isle Rlty & Dev Co Inc

Listing courtesy of Tri-Isle Rlty & Dev Co Inc.

281 Maha Rd Unit Unit A, Makawao $1,100,000

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 b...

ACTIVE Status
410399 MLS
Fee Simple Tenure

Courtesy of Coldwell Banker Island Prop-Ku

Listing courtesy of Coldwell Banker Island Prop-Ku.

305 Iini Way, Makawao $1,390,000 ▼

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 r...

ACTIVE Status
4 Beds
4 Baths
410393 MLS
Fee Simple Tenure

Courtesy of Equity One Real Estate Inc (M)

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

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 $1,350,000 ▼

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