Makawao/Olinda/Haliimaile Homes for Sale

Welcome to the enchanting neighborhoods of Makawao, Olinda, and Haliimaile, nestled in the lush, green hills of Maui, Hawaii. Renowned for their rich history and vibrant culture, these charming communities offer a unique blend of island living and rural tranquility.

Makawao, often referred to as the "Paniolo (cowboy) Town," is steeped in Hawaiian ranching history, boasting a plethora of art galleries, boutiques, and local eateries that celebrate the spirit of the island. Stroll down Baldwin Avenue and immerse yourself in the warm, welcoming atmosphere, where the community gathers for events and festivals throughout the year.

Just a short drive away, Olinda captivates with its breathtaking views and cooler climate, making it a favorite spot for those seeking a serene retreat. The neighborhood is dotted with beautiful homes, many of which feature expansive gardens and stunning vistas of the Pacific Ocean and neighboring islands.

Haliimaile, a quaint community with a rich agricultural heritage, offers a peaceful escape while still being close to the amenities of Makawao. The area is known for its lush landscapes and friendly neighbors, making it an ideal place for families and nature lovers alike.

For those considering a move to this idyllic region, there are a variety of homes for sale that cater to different tastes and budgets. Whether you’re looking for a cozy cottage or a sprawling estate, the real estate options in Makawao, Olinda, and Haliimaile are as diverse as the landscape itself. Embrace the Hawaiian lifestyle and discover your dream home in these beautiful neighborhoods today!

Newest Makawao/Olinda/Haliimaile Homes for Sale

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.

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

Courtesy of Keller Williams Realty Maui-Ka

Listing courtesy of Keller Williams Realty Maui-Ka.

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