Makawao/Olinda/Haliimaile Homes with Detached Ohana

Makawao/Olinda/Haliimaile Homes with Detached Ohana

Welcome to the enchanting neighborhoods of Makawao, Olinda, and Haliimaile, nestled in the lush upcountry of Maui, Hawaii. This vibrant region is not only known for its stunning vistas and rich cultural heritage but also for its welcoming community and unique lifestyle.

Makawao, a charming town with a rich paniolo (cowboy) history, is home to a delightful mix of boutiques, art galleries, and eateries that celebrate local flavors. Just a stone's throw away, Olinda offers breathtaking views of the coastline and is renowned for its cooler climate, making it a perfect retreat from the tropical heat. Haliimaile, a quaint community, is known for its agricultural roots and the famous Haliimaile Pineapple Company, providing a glimpse into Maui's farming heritage.

One of the standout features of homes in this area is the availability of detached 'Ohana units. These separate living spaces provide the perfect solution for multi-generational families or those seeking additional rental income. Imagine having a cozy guest suite or a private office just steps away from your main home, all while enjoying the serenity of the lush surroundings.

Living in Makawao, Olinda, or Haliimaile means embracing a lifestyle that blends the beauty of nature with the warmth of community. With easy access to hiking trails, farmers' markets, and local events, you'll find endless opportunities to connect with your neighbors and the land. Whether you're looking for a family home or a serene retreat, this upcountry paradise offers a unique blend of comfort and charm that is truly unmatched. Embrace the spirit of aloha and discover your dream home in this idyllic corner of Maui!

Newest Makawao/Olinda/Haliimaile Homes with Detached Ohana

$2,649,000
5 Beds ⋅ 4 Baths ⋅ 410159 MLS ⋅ Fee Simple Tenure
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 timeless charm. The property lies on 4.38 acres of vibrant, open land. It could be your own little oasis, with lush landscaping and tranquility within a short driving distance to charming Makawao Town. The main residence is custom-built with rich redwood walls on both the interior and exterior, a dramatic fireplace hearth formed from black lava rock, teak bannisters, and other handcrafted architectural details throughout. The brand-new deck stretches around the home, providing glorious views of both the mountains and the North Shore. This home was built with love, and the living experience is sure to be warm and absolutely unforgettable. Beyond the primary residence, this property boasts a separate cottage with its own private entrance. This second dwelling offers exceptional flexibility for guests, extended family, or even rental potential.

1740 Piiholo Rd, Makawao

Listing courtesy of Coldwell Banker Island Prop(S).

$2,395,000
5 Beds ⋅ 4 Baths ⋅ 409724 MLS ⋅ Fee Simple Tenure
This unique multi-unit property (4 structures, 8 units) offers a rare opportunity for investors seeking strong cash flow and long-term upside. There are 5 one bedroom units, and 3 two bedroom units. Situated on just over half an acre, the property features four separate structures with a total of eight tenant-occupied units, creating an income-producing compound in one of Upcountry Maui’s most desirable locations. Tenants enjoy dedicated parking, on-site laundry, and the convenience of being moments from Makawao’s shops, restaurants, galleries, and local charm. Numerous improvements have already been completed, making this an attractive opportunity for an investor looking to step into an established rental property with immediate income potential. The property also has 3 water meters. Listing includes photos of one of the 8 units. A truly one-of-a-kind upcountry investment property.

15 Olinda Rd, Makawao

Listing courtesy of eXp Realty.

$1,495,000
3 Beds ⋅ 2 Baths ⋅ 407661 MLS ⋅ Fee Simple Tenure
Welcome to 1199 Freitas Place in Makawao town — a well-cared-for home that combines functional design with classic island living. This is truly one of the best values in Makawao on a $/sf basis! The property features a 1635 square foot, 3-bed/2-bath main residence and a 667 square foot detached Ohana. Both structures are situated on a lush 0.39 acre corner lot with established fruit trees and versatile outdoor spaces. The main home has been freshly repainted and maintained with great attention to detail. Its thoughtful layout provides a welcoming atmosphere with space for relaxation and entertaining. The separate Ohana, previously used as a hair salon, offers an open floor plan ready to be tailored to your needs — whether as an additional living area, creative workspace, or guest suite. The fenced-in yard showcases a diverse fruit orchard featuring mountain apples, oranges, tangerines, lemons, limes, bananas, peaches, curry leaf, Suriname cherries, ginger and turmeric. Additional structures include a workspace and storage shed, offering flexibility for hobbies or projects, an ocean view deck for relaxing or sunset dinners, and a large generator to keep the home fully powered during outages. The dryer, cooktop and oven are all gas powered. Owners average electric bill has been less than $100/month! Located within walking distance of Makawao Town and Makawao Elementary School, you’ll enjoy the convenience of local shops, dining, and community events, all while feeling tucked away in your own private oasis. This is a property that’s been genuinely cared for, offering a lifestyle that blends nature, creativity, and Maui comfort.

1199 Freitas Pl, Makawao

Listing courtesy of Compass-W.

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