10 most expensive homes for sale in Makawao/Olinda/Haliimaile
In Makawao/Olinda/Haliimaile the median sale price for homes on the market is about -, however, high-end properties can be listed at a much higher price point. Here are the top ten most expensive homes for sale in Makawao/Olinda/Haliimaile (Maui).
$2.5m ▼ $100,000
1065 Ehu Rd, Makawao
Home
5
bd
4
ba
3,264
sqft
$2,495,000 ▼ $100,000
5
bd 4
ba 3,264
sqft
bd 4
ba 3,264
sqft
Home for sale
1065 Ehu Rd Makawao, Maui
Private Forest Retreat on 2.13 Acres Bordering the majestic Makawao Forest Reserve and set above a peaceful gulch, this exceptional Upcountry estate offers the perfect blend of privacy, flexibility, and natural beauty. Located in the highly desirable Pi?iholo area—known for its crisp air, lush landscape, and serene forest setting—this fully fenced property sits at the end of a quiet cul-de-sac, just 12 minutes from historic Makawao town. The main home spans 3,264 sq ft with 5 BD and 4 full BA, featuring vaulted ceilings, elegant Marbau wood floors, travertine bathrooms, and in-floor central heating—ideal for cooler Upcountry mornings. Designed with openness and warmth in mind, the floor plan lends itself to relaxed living and entertaining. On the opposite end of the property, the detached Ohana offers 1,232 sq ft of comfortable living space with 3 BD, 2 BA, extended lanai space and a sizable 560 sq ft garage —perfect for extended family, long-term rental, or visiting guests. Additional amenities include a one-car garage with a connected exercise room and art studio, and a charming tiny home with a full kitchen and expansive lanai—ideal for a caretaker, guest hideaway, or creative retreat. The gently sloped acreage is dotted with mature fruit trees—including avocado, apple, grapefruit, orange, lemon, and peach—and surrounded by the tranquil sights and sounds of nature. Wake to the chirping of forest birds and savor the peaceful energy of Pi'iholo’s higher elevation. Whether you're looking for a multigenerational compound, income-generating property, or a private sanctuary immersed in nature, this one-of-a-kind retreat delivers Upcountry living at its best.
$2.13m ▼ $170,000
128 Hoopalua Dr, Makawao
Home
3
bd
2
ba
2,560
sqft
$2,125,000 ▼ $170,000
3
bd 2
ba 2,560
sqft
bd 2
ba 2,560
sqft
Home for sale
128 Hoopalua Dr Makawao, Maui
This is an amazing and RARE opportunity to own a SINGLE LEVEL home and POOL in Kula 200! Put your own touches and remodeling ideas together for this home with great bones! You'll appreciate the gigantic living room with stone fireplace, a gorgeous open beam ceiling, and views out to the pool! Enjoy the generous den or game room where you and your loved ones or pals can casually relax. In addition to all of this, there is a luxuriously sized primary bedroom opening out to the pool. This is one of the few locations Upcountry that you can truly enjoy a swimming pool! And, you gotta love that outside shower and original pool slide! This 2 acre parcel boasts an elegant Monkey Pod tree, planted by the Owners. The lychee and mango produce beautifully. The location, architecture and price make this an irresistible purchase. Better than that, it could be HOME SWEET HOME.
Home
1
bd
2
ba
1,304
sqft
$2,095,000
1
bd 2
ba 1,304
sqft
bd 2
ba 1,304
sqft
Home for sale
1854 Olinda Rd Makawao, Maui Neighborhood: Olinda
A rare 5-acre offering along the highly desired upper stretch of Olinda Road, this property delivers the kind of views and setting that define Upcountry living. Positioned beside Haleakala Ranch core lands, the acreage opens toward sweeping bi-coastal vistas, South Shore sunsets, and the rolling pastureland that makes Olinda so treasured. Framed by a striking jacaranda, a towering ficus, and mature landscaping that has evolved over decades, the land carries both history and potential. Multiple vantage points at higher elevations reveal some of the property’s most impressive outlooks—expansive, cinematic, and uniquely private. Improvements on the property include the main house, a secondary rental unit, and a separate art studio. These structures reflect the charm of an earlier era and offer flexible footprints for those looking to update or reimagine the spaces. Many buyers will approach the property with a vision for renovation or new construction to fully maximize the land’s potential. What remains highly valuable is the combination of acreage, established concrete infrastructure, County water service, and a remarkable setting rarely available in this part of Makawao/Olinda.
$2m ▼ $201,000
1365 Piiholo Rd, Makawao
Home
3
bd
2
ba
3,433
sqft
$1,999,000 ▼ $201,000
3
bd 2
ba 3,433
sqft
bd 2
ba 3,433
sqft
Home for sale
1365 Piiholo Rd Makawao, Maui
Discover tranquility and ultimate privacy at this exceptional Upcountry Maui estate. Nestled on the slopes of Haleakala and bordered by a lush gulch, this 3,433 sqft residence and detached cottage are set on two sprawling acres, creating a serene personal retreat. Step into the main home and you will be greeted by an inviting atmosphere. With soaring vaulted ceilings and large picture windows that perfectly frame the expansive ocean views, you will feel like you have nowhere else to be. The recently remodeled kitchen allows you to seamlessly transition to outdoor living on the generous wrap-around lanai, and enjoy breathtaking sunsets year-round. The primary bedroom is on the main floor and the home also has a loft space, perfect for an art studio or yoga space. This home is both expansive, yet cozy, creating a perfect sanctuary. The lower level offers incredible flexibility with a spacious 2-bedroom, 1-bathroom suite, ideal for extended family or guests, as well as a detached cottage that is seperately metered, and has it's own driveway & entrance. Attached to the main home is a 1 car garage as well as a separate 2 car carport along with plenty of space for storage. This is a rare chance to own a versatile and secluded piece of paradise, where the beauty of Upcountry living unfolds around you.
Home
2
bd
2
ba
1,542
sqft
$1,900,000
2
bd 2
ba 1,542
sqft
bd 2
ba 1,542
sqft
Home for sale
2640 Olinda Rd Makawao, Maui Neighborhood: Olinda
Discover a private, tranquil sanctuary nourished by nature. The lovingly cared for 2.6+ acres includes a perfectly positioned little Koa Forest by the Main House & a Redwood Grove by the Ohana, both planted 70 years ago. They're enchanting and invite wandering. Other mature trees include Redwood, Cedar, Orange, Lemon, Tangerine, Loquat, Jacaranda, & a Coffee Tree Hedge. The Main Home featuring redwood walls, hardwood floors, and fireplaces in the large living room & dining room embodies the Charm and History of Upcountry Maui. Expansive windows frame the lush landscape and invite ocean views inside. Owned PV & available fiber optic internet. This property offers an immersive experience, from the scent of cedar and eucalyptus in the air to daily walks at the nearby Waihou Spring Trail. Adding significant value and flexibility, is a private 3 bedroom, 1.5 bath Ohana at the opposite end of the property bordering state land. Recently refreshed with new paint, bamboo flooring, stove, & light fixtures it offers that immediate 2nd living space while updating the main home, multi generational living, rental, or perhaps looking into the possibilities of a CPR. No road sign at the property & do not enter without an appointment. Preapproval or Proof of Funds required for showings.
Home
4
bd
3
ba
1,456
sqft
$1,825,000
4
bd 3
ba 1,456
sqft
bd 3
ba 1,456
sqft
Discover Hokuula in the quaint town of Haliimaile, nestled on the gentle slopes of Haleakala, overlooking Maui’s world-renowned Northshore coastline. Expansive ocean and mountain views will greet you from this soon to be Upcountry community of 196-single family homes. Featuring contemporary architecture with six unique, 4-bedroom models on lots of approximately 7,500 to 10,000 square feet. Hokuula offers a variety of diverse floor plans in single and two-story designs. In addition, ohana dwellings are available on various lots, providing even more versatility. Each home has been thoughtfully designed. This single-story Floor Plan A home has 4 bedrooms and 3 bathrooms. Features include an open floor plan, 9 foot ceilings, split AC, rain gutters, covered lanai, attached two car garage. Highlighted amenities consist of stainless-steel appliances, double paned windows, soft close cabinetry. A walking path around the perimeter of the community will provide another way to enjoy the panoramic views from Hali?imaile. Located just a few minutes from the modern conveniences of Kahului as well as the quaint charms of Paia and Makawao. This is truly a unique opportunity to own your piece of paradise on Maui, a wonderful place to call home. Developer reserves the right to modify floor plans, elevations, specifications, features, and prices without prior notice. Square footage and room sizes are approximate. All renderings and floor plans are conceptual and are not intended to be an actual depiction of the home, driveway, or landscaping. Prices vary between floor plan and lot selections along with view corridors. Buyer and Buyer's Agent to conduct due diligence.
Home
4
bd
3
ba
2,280
sqft
$1,725,000
4
bd 3
ba 2,280
sqft
bd 3
ba 2,280
sqft
Discover Hoku’ula in the quaint town of Haliimaile, nestled on the gentle slopes of Haleakala, overlooking Maui’s world-renowned Northshore coastline. Expansive ocean and mountain views will greet you from this soon to be Upcountry community of 196-single family homes. Featuring contemporary architecture with six unique, 4-bedroom models on lots of approximately 7,500 to 10,000 square feet. Hoku’ula offers a variety of diverse floor plans in single and two-story designs. In addition, ohana dwellings are available on various lots, providing even more versatility. Each home has been thoughtfully designed. This upstairs living F floor plan home has 4 bedrooms and 2.5 bathrooms. Features include an open floor plan, 9 foot ceilings, split AC, rain gutters, covered lanai, attached two car garage. Highlighted amenities consist of stainless-steel appliances, double paned windows, soft close cabinetry. A walking path around the perimeter of the community will provide another way to enjoy the panoramic views from Hali?imaile. Located just a few minutes from the modern conveniences of Kahului as well as the quaint charms of Paia and Makawao. This is truly a unique opportunity to own your piece of paradise on Maui, a wonderful place to call home. Developer reserves the right to modify floor plans, elevations, specifications, features, and prices without prior notice. Square footage and room sizes are approximate. All renderings and floor plans are conceptual and are not intended to be an actual depiction of the home, driveway, or landscaping. Prices vary between floor plan and lot selections along with view corridors. Buyer and Buyer's Agent to conduct due diligence.
Home
4
bd
3
ba
1,888
sqft
$1,685,000
4
bd 3
ba 1,888
sqft
bd 3
ba 1,888
sqft
Home for sale
1115 Pookela Rd Makawao, Maui Neighborhood: Makawao
Welcome to your luxury upcountry home, just a short stroll to Makawao Town but worlds apart. This 4 bedroom, 3 bath house is located at the bottom of a gated driveway inside a master planned development, providing privacy and a "front row seat" on the panoramic, bi-coastal ocean views found there. Upstairs you will find the great room, 3 bedrooms, 2 baths and a spacious, partially covered deck (already roughed in for a hot tub) with elevated north and south shore views. The 4th bedroom and 3rd bath are located on the lower level with a family room and separate entrance, providing a flexible living space that is also perfect for extended family or guests. The spacious 2 car garage has storage alcoves for all the Maui toys, as well as a large workshop area and separate storage room inside. Two outdoor sheds provide additional storage. Other extras include an owned, 24 panel PV solar system on a net meter, a level 2 EV charger, and hard wired surround sound and deck speakers. This home is built to last with lpe decking, hardie board siding, and copper flashings on the exterior, along with bamboo and tiger wood flooring and natural stone interiors. It is sold turn-key, and includes high end custom furnishings. Owner's personal items inside the garage are excluded. This is a Residential CPR. Buyer and Buyer's Agent shall do their own due diligence regarding the use and structures on the property. Owner listed.
Home
4
bd
3
ba
1,960
sqft
$1,675,000
4
bd 3
ba 1,960
sqft
bd 3
ba 1,960
sqft
Discover Hokuula in the quaint town of Haliimaile, nestled on the gentle slopes of Haleakala, overlooking Maui’s world-renowned Northshore coastline. Expansive ocean and mountain views will greet you from this soon to be Upcountry community of 196-single family homes. Featuring contemporary architecture with six unique, 4-bedroom models on lots of approximately 7,500 to 10,000 square feet. Hokuula offers a variety of diverse floor plans in single and two-story designs. In addition, ohana dwellings are available on various lots, providing even more versatility. Each home has been thoughtfully designed. This upstairs living design, D floor plan home, has 4 bedrooms and 3 bathrooms. Features include an open floor plan, 9 foot ceilings, split AC, rain gutters, covered lanai, attached two car garage. Highlighted amenities consist of stainless-steel appliances, double paned windows, soft close cabinetry. A walking path around the perimeter of the community will provide another way to enjoy the panoramic views from Hali?imaile. Located just a few minutes from the modern conveniences of Kahului as well as the quaint charms of Paia and Makawao. This is truly a unique opportunity to own your piece of paradise on Maui, a wonderful place to call home. Developer reserves the right to modify floor plans, elevations, specifications, features, and prices without prior notice. Square footage and room sizes are approximate. All renderings and floor plans are conceptual and are not intended to be an actual depiction of the home, driveway, or landscaping. Prices vary between floor plan and lot selections along with view corridors. Buyer and Buyer's Agent to conduct due diligence.
Home
4
bd
4
ba
2,095
sqft
$1,625,000
4
bd 4
ba 2,095
sqft
bd 4
ba 2,095
sqft
Discover Hokuula in the quaint town of Haliimaile, nestled on the gentle slopes of Haleakala, overlooking Maui’s world-renowned Northshore coastline. Expansive ocean and mountain views will greet you from this soon to be Upcountry community of 196-single family homes. Featuring contemporary architecture with six unique, 4-bedroom models on lots of approximately 7,500 to 10,000 square feet. Hokuula offers a variety of diverse floor plans in single and two-story designs. In addition, ohana dwellings are available on various lots, providing even more versatility. Each home has been thoughtfully designed. This luxuriously laid out E floor plan has 4 bedrooms and 3.5 bathrooms. Features include an open floor plan, 9 foot ceilings, covered lanai, attached two car garage. Highlighted amenities consist of stainless-steel appliances, double paned windows, soft close cabinetry, Split AC and Rain Gutters. A walking path around the perimeter of the community will provide another way to enjoy the panoramic views from Hali?imaile. Located just a few minutes from the modern conveniences of Kahului as well as the quaint charms of Paia and Makawao. This is truly a unique opportunity to own your piece of paradise on Maui, a wonderful place to call home. Developer reserves the right to modify floor plans, elevations, specifications, features, and prices without prior notice. Square footage and room sizes are approximate. All renderings and floor plans are conceptual and are not intended to be an actual depiction of the home, driveway, or landscaping. Prices vary between floor plan and lot selections along with view corridors. Buyer and Buyer's Agent to conduct due diligence.
* information deemed reliable, but not guaranteed
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