Makawao/Olinda/Haliimaile Homes with Mountain(s) View

4 Beds ⋅ 4 Baths ⋅ 410393 MLS ⋅ Fee Simple Tenure

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 roof conveniently located in Makawao. The well-designed floor plan places the spacious living and dining areas at the center of the home, separating two bedrooms on each side to provide both privacy and functionality. The remodeled kitchen features custom cabinetry, a gas range, and a convenient pass-through window to the outdoor dining area, making entertaining a breeze. This versatile space can also serve as a covered carport when desired. Recent upgrades include luxury vinyl plank flooring, split A/C throughout, instant water heater shared by primary bath and 2nd bedroom bath, and numerous thoughtful updates throughout. Beyond the dining area, the covered pavilion and expansive interlocking deck tile patio create an inviting outdoor retreat with plenty of room for relaxing, entertaining, or enjoying Makawao's comfortable Upcountry climate. 305 Iini Way—a home you'll be longing to come home to.

305 Iini Way, Makawao

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

$2,395,000

5 Beds ⋅ 4 Baths ⋅ 409724 MLS ⋅ Fee Simple Tenure

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 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.

$2,395,000

11 Beds ⋅ 8 Baths ⋅ 409725 MLS ⋅ Fee Simple Tenure

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-term upside. There are 5 one bedroom units, and 3 two bedroom units. Situated on just over half an acre, the property features 4 separate structures with a total of 8 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.

$1,150,000

3 Beds ⋅ 2 Baths ⋅ 408939 MLS ⋅ Fee Simple Tenure

Your whole family will have space in this energy efficient, turnkey, Bungalow Style, multi-level "Mini Mansion" It's nestled Upcountry on Haleakala. Walking distance to schools and Historical Makawao Town and short drive to town, beaches, and airport. 3 bedroom 2 baths can be divided into a separate 1 bd 1 ba attached ohana with private yard, kitchen, driveway, and entrance that easily could be rented. A new perimeter fence has created 5 enclosed unique yards. Living on a private road is safe for kids and pets. Extra large, tall carport with a workshop and observation deck on top with an incredible view creates one of the best spaces on the property. Pictures don't do it justice I'm able to email more detailed pictures I look forward to hearing from you. All comments, data is provided by seller or seller's representatives. Buyer to confirm all & hold all parties harmless from any discrepancy data in the mls and advertising. Limited Service–Data Entry Addendum signed by seller/s must be signed by buyer/s with Purchase Contract.

3586 Kalua Pl, Makawao

Listing courtesy of Nathalie Mullinix Rlty Universal Inc.

$1,399,000

3 Beds ⋅ 2 Baths ⋅ 408348 MLS ⋅ Fee Simple Tenure

Bring your vision to this peaceful Upcountry property nestled just below the cool cloud line of Upper Piiholo. Set on two (2) beautifully established acres, this three (3) bedroom two (2) bath home offers more than twenty six hundred (2600+) square feet of interior space along with views that create an inspiring backdrop for a thoughtful renovation. Native trees, tall pines, and fragrant eucalyptus surround this property, offering both privacy and a deep connection to the land. The home is ready for someone who appreciates character and craftsmanship and wants to restore it to its original charm. A generous wraparound deck already frames the exterior, inviting a seamless indoor and outdoor lifestyle. Inside, the main level features an open living, dining and kitchen area with vaulted ceilings and a striking stone accented fireplace. Two (2) bedrooms and a full bath completes this floor. The primary suite rests on the upper level, offering treetop views and natural light. The finished basement offers a one (1) car parking garage and a large room, perfect for a home office, home theatre or possibly a work out/yoga studio. With internet available and plenty of room to reimagine both indoor and outdoor spaces, this property is a rare opportunity to create something truly special. Whether you update the existing layout or transform it into a more modern Upcountry retreat, the setting and foundation are already in place. This much loved home is waiting for its next chapter.

2400 Piiholo Rd, Makawao

Listing courtesy of Coldwell Banker Island Prop(Ka).

$4,037,500

408107 MLS ⋅ Fee Simple Tenure

** Sale includes MLS #s 408092, 408093, 408094, 408095, 408096, 408097, 408098, 408099, 408100, 408101, 408143, 408102, 408103, 408104, 408106 & 408107 ** Rare opportunity to acquire a multi-site land portfolio spanning Wailuku, Kihei, and Makawao—three of Maui’s most sought-after and growing regions. The portfolio consists of 16 parcels totaling approximately 272.055 acres, offering significant scale, diverse topography, and strategic locations suitable for investment, master planning, or phased development. Properties are offered for sale exclusively as a single portfolio. Any individual parcel pricing shown is for MLS compliance purposes only and does not reflect standalone availability or value. The portfolio purchase price is $48,000,000.00

Makani Rd, Makawao

Listing courtesy of Commercial Prop of Maui LLC.

$1,084,100

408106 MLS ⋅ Fee Simple Tenure

** Sale includes MLS #s 408092, 408093, 408094, 408095, 408096, 408097, 408098, 408099, 408100, 408101, 408143, 408102, 408103, 408104, 408106 & 408107 ** Rare opportunity to acquire a multi-site land portfolio spanning Wailuku, Kihei, and Makawao—three of Maui’s most sought-after and growing regions. The portfolio consists of 16 parcels totaling approximately 272.055 acres, offering significant scale, diverse topography, and strategic locations suitable for investment, master planning, or phased development. Properties are offered for sale exclusively as a single portfolio. Any individual parcel pricing shown is for MLS compliance purposes only and does not reflect standalone availability or value. The portfolio purchase price is $48,000,000.00

Makani Rd, Makawao

Listing courtesy of Commercial Prop of Maui LLC.

$12,230,500

408104 MLS ⋅ Fee Simple Tenure

** Sale includes MLS #s 408092, 408093, 408094, 408095, 408096, 408097, 408098, 408099, 408100, 408101, 408143, 408102, 408103, 408104, 408106 & 408107 ** Rare opportunity to acquire a multi-site land portfolio spanning Wailuku, Kihei, and Makawao—three of Maui’s most sought-after and growing regions. The portfolio consists of 16 parcels totaling approximately 272.055 acres, offering significant scale, diverse topography, and strategic locations suitable for investment, master planning, or phased development. Properties are offered for sale exclusively as a single portfolio. Any individual parcel pricing shown is for MLS compliance purposes only and does not reflect standalone availability or value. The portfolio purchase price is $48,000,000.00

11047 Haleakala Hwy, Makawao

Listing courtesy of Commercial Prop of Maui LLC.

$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.

Makawao/Olinda/Haliimaile Homes with Mountain(s) View

Newest Makawao/Olinda/Haliimaile Homes with Mountain(s) View