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Makawao/Olinda/Haliimaile Real Estate

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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

1018 Ulele St Unit Unit B, Makawao image
1018 Ulele St Unit Unit B, Makawao $744,000

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...

  • ACTIVE Status
  • 2 Beds
  • 1 Baths
  • 411070 MLS
  • Fee Simple Tenure
Courtesy of Keller Williams Realty Maui-Ka

Listing courtesy of Keller Williams Realty Maui-Ka.

11 Huliamahi Pl Unit Unit B, Makawao image
11 Huliamahi Pl Unit Unit B, Makawao $750,000

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...

  • ACTIVE Status
  • 411001 MLS
  • Fee Simple Tenure
Courtesy of The Maui Real Estate Team Inc

Listing courtesy of The Maui Real Estate Team Inc.

143 Leiohu Cir, Makawao image
143 Leiohu Cir, Makawao $2,641,000

Enjoy cool upcountry breezes, bicoastal views and the convenience of nearby Makawao Town in this thoughtfully upgraded ranch style residence. Situated in a gated communit...

  • ACTIVE Status
  • 3 Beds
  • 3 Baths
  • 410991 MLS
  • Fee Simple Tenure
Courtesy of Keller Williams Realty Maui-Ki

Listing courtesy of Keller Williams Realty Maui-Ki.

1199 Freitas Pl Pl, Makawao image
1199 Freitas Pl Pl, Makawao $1,200,000

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 e...

  • ACTIVE Status
  • 3 Beds
  • 2 Baths
  • 410916 MLS
  • Fee Simple Tenure
Courtesy of Chris Bakeman Realty LLC

Listing courtesy of Chris Bakeman Realty LLC.

640 Makawao Ave, Makawao image
640 Makawao Ave, Makawao $1,549,000 ▼

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.

1102 Mailuna Pl, Makawao image
1102 Mailuna Pl, Makawao $1,475,000 ▼

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 image
30 Pahaa Pl, Makawao $1,095,000 ▼

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 image
3566 Kalua Pl, Makawao $750,000 ▼

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 image
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 image
305 Iini Way, Makawao $1,333,333 ▼

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 image
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 image
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).

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Christopher Barca | Compass 3620 Baldwin Ave, Suite 103A
Makawao, HI 96768
License RB-20936
Cell: (808) 269-1053 christopher.barca@compass.com

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Compass Maui Real Estate

Compass is a licensed real estate brokerage serving Hawaii communities. We adhere to all applicable fair housing laws. All information provided is deemed reliable but not guaranteed and is subject to change without notice, including price, availability, or condition. No representation or warranty is made regarding the accuracy of property details. All measurements and square footage are approximate. This content is not intended to solicit properties already listed. Nothing contained herein should be considered legal, tax, or professional advice outside the scope of real estate brokerage services.

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