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  ›Makawao, Olinda, Haliimaile   ›Pukalani   ›Kula, Ulupalukua, Kanaio

Makawao Real Estate Listings

Makawao is a quaint community in the beautiful upcountry area of Maui. The town is also known as Maui’s Paniolo or cowboy town. This traces back to the era when cattle ranching was prime industry on the slopes of Haleakala above town. The town’s cowboy legacy is still evident when the rodeo comes to town every year on 4th of July weekend and in the architecture. These days, you are more likely to find a nice restaurant, gallery or shop than a feed store when you walk the streets of Makawao. The charm of downtown Makawao has contributed to the desirability of the local real estate market. Homes in the community range from modest starter homes, to old plantation style charmers to estate properties with spectacular views. The diversity of homes increases when you include the nearby communities of Olinda and Hali’imaile under the umbrella of Makawao. Olinda is beautiful area of meadows and forest located above Makawao. Tall eucalyptus trees and pines thrive in the cooler air of this part of the island. Hali’imaile is a community that was based on pineapple farming in the area. There are number of older historic homes that were the one time home to the pineapple workers who worked in the fields. Scroll through the page below to see the homes listed for sale in the Makawao area.

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Displaying results 1 - 20 of 25
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3077 Baldwin in Makawao/Olinda/Haliimaile

MLS Number: 376322 Bedrooms: 3
Status: ACTIVE Baths: 4.00
Acreage: 6.6300 acres (approx) Interior:2968 sq. ft. (approx)
Price: $3,500,000 Fee Simple Listed By: Hawaii Life (W)

Experience the timeless of a Plantation Estate. Designed by renowned architect, Charles W. Dickey, the home was built in 1938 and has had only two owners. Expansive, beau...

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47 Naniuka in Makawao/Olinda/Haliimaile

MLS Number: 378499 Bedrooms: 3
Status: PENDING - CONT. TO SHOW Baths: 3.50
Acreage: 2.5500 acres (approx) Interior:3302 sq. ft. (approx)
Price: $1,470,000 Fee Simple Listed By: Big Wave Realty LLC

Enjoy the stunning ocean views from this ultra private, well-designed, new custom home in Upcountry Maui. This 3-bedroom, 3.5-bathroom home of 3,302 square feet has been...

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429 Hoopalua in Makawao/Olinda/Haliimaile

MLS Number: 378038 Bedrooms: 4
Status: ACTIVE Baths: 3.50
Acreage: 3.3900 acres (approx) Interior:3854 sq. ft. (approx)
Price: $2,470,000 Fee Simple Listed By: Island Sotheby's Int'l Rlty(M)

This quintessential Kama’aina pole home is casual yet elegant and is is privately nestled on this large (3.3+ acre) top choice of all the lots in Kula 200. Featuring bi...

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12 EHU in Makawao/Olinda/Haliimaile

MLS Number: 378496 Bedrooms: 4
Status: ACTIVE Baths: 3.50
Acreage: 2.0202 acres (approx) Interior:2584 sq. ft. (approx)
Price: $875,000 Fee Simple Listed By: La Costa Realty Hawai'i LLC

Two homes are sited on this huge 2.32 acre lot. There are many possibilities with these homes and lot with mature fruit trees and many flowers. Cesspool was just replac...

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3531 Baldwin in Makawao/Olinda/Haliimaile

MLS Number: 378326 Bedrooms: 4
Status: ACTIVE Baths: 3.00
Acreage: 0.2843 acres (approx) Interior:2600 sq. ft. (approx)
Price: $1,290,000 Fee Simple Listed By: NextHome Pacific Properties

This delightful house and cottage is located in the heart of Makawao Town, just steps to stores, restaurants, and shopping. Surrounded by lush trees and pastoral views, t...

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1420 Piiholo in Makawao/Olinda/Haliimaile

MLS Number: 378011 Bedrooms: 4
Status: PENDING - CONT. TO SHOW Baths: 3.00
Acreage: 1.3800 acres (approx) Interior:2240 sq. ft. (approx)
Price: $989,000 Fee Simple Listed By: Coldwell Banker Island Prop(Ka)

This is a UNIQUE opportunity. Situated along Piiholo Road, nestled on 1.38 acres of land, sits 3 structures awaiting it's next owner. Offering both indoor an outdoor c...

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1 Alaluana in Makawao/Olinda/Haliimaile

MLS Number: 377468 Bedrooms: 4
Status: ACTIVE Baths: 3.00
Acreage: 1.4600 acres (approx) Interior:4276 sq. ft. (approx)
Price: $950,000 Fee Simple Listed By: Millennium Realty, Inc.

Incredible opportunity for the owner builder or contractor to finish this master piece of a HOME! This well designed 5 bedroom 3 bath 2-story home is done to the "rough ...

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115 Hawea in Makawao/Olinda/Haliimaile

MLS Number: 374853 Bedrooms: 3
Status: ACTIVE Baths: 3.00
Acreage: 2.9080 acres (approx) Interior:2366 sq. ft. (approx)
Price: $1,350,000 Fee Simple Listed By: Coldwell Banker Island Prop(S)

Unique custom 3 bedroom home in magical Olinda just 2.5 miles above Makawao Town. Feast your eyes on the gorgeous views from large windows throughout the house. Beautiful...

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1079 Maohu in Makawao/Olinda/Haliimaile

MLS Number: 378223 Bedrooms: 5
Status: PENDING - CONT. TO SHOW Baths: 3.00
Acreage: 0.2142 acres (approx) Interior:2492 sq. ft. (approx)
Price: $789,000 Fee Simple Listed By: KW Island Living (Ka)

Upcountry living with room for extended family in a charming two level home! Well maintained country home on a flag lot with lots of fruit trees, a vegetable garden and p...

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2725 Olinda in Makawao/Olinda/Haliimaile

MLS Number: 376519 Bedrooms: 6
Status: ACTIVE Baths: 3.00
Acreage: 59.7900 acres (approx) Interior:4490 sq. ft. (approx)
Price: $3,800,000 Fee Simple Listed By: Island Sotheby's Int'l Rlty(M)

Beautifully and privately situated atop the hills of Olinda, this historic 60 acre Upcountry estate is a treasure to behold! Built in 1912, a wealth of Maui's history run...

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726 Pelenaka in Makawao/Olinda/Haliimaile

MLS Number: 378607 Bedrooms: 3
Status: ACTIVE Baths: 2.50
Acreage: 0.1711 acres (approx) Interior:1305 sq. ft. (approx)
Price: $745,000 Fee Simple Listed By: KW Island Living (Ka)

Beautiful 3 bedroom, 2.5 bath immaculate and meticulously maintained home in Makawao. This MOVE IN READY tropical Oasis is in walking distance to Makawao town and Seabur...

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2625 Olinda in Makawao/Olinda/Haliimaile

MLS Number: 372600 Bedrooms: 3
Status: PENDING - CONT. TO SHOW Baths: 2.50
Acreage: 4.1730 acres (approx) Interior:1982 sq. ft. (approx)
Price: $998,000 Fee Simple Listed By: Hawaii Life (W)

A true Maui legacy estate offering mountain and ocean views from the top of Olinda Road in cool and quiet upcountry Maui. The main home features over 1900sqft of living ...

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1879 & 1875 Olinda in Makawao/Olinda/Haliimaile

MLS Number: 377983 Bedrooms: 3
Status: ACTIVE Baths: 2.50
Acreage: 4.2626 acres (approx) Interior:2685 sq. ft. (approx)
Price: $3,195,000 Fee Simple Listed By: Maui Home and Life

Maui Sanctuary Estate! Privacy, tranquility, serenity, harmony. A Unique one-of-a-kind, magical oasis—with total privacy.. A classy, comfortable home, tastefully featur...

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71 C Miner in Makawao/Olinda/Haliimaile

MLS Number: 377003 Bedrooms: 2
Status: ACTIVE Baths: 2.00
Acreage: 0.7984 acres (approx) Interior:832 sq. ft. (approx)
Price: $450,000 Fee Simple Listed By: Hawaii Life (W)

Attractive 2 bedroom, 2 bathroom home conveniently located close to Makawao town. Perched on a hill, there are beautiful ocean views. There's a private side yard and spa...

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88 Alaluana in Makawao/Olinda/Haliimaile

MLS Number: 378324 Bedrooms: 3
Status: ACTIVE Baths: 2.00
Acreage: 2.7900 acres (approx) Interior:1551 sq. ft. (approx)
Price: $770,000 Fee Simple Listed By: Island Sotheby's Int'l Rlty(W)

Beautiful home in excellent shape near the top of Olinda, elevation is about 3500 ft. Quiet and private, well-built Victorian-style three-bedroom, two bath home on nearly...

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1269 Pohuli in Makawao/Olinda/Haliimaile

MLS Number: 377359 Bedrooms: 3
Status: PENDING - CONT. TO SHOW Baths: 2.00
Acreage: 0.1491 acres (approx) Interior:1248 sq. ft. (approx)
Price: $519,000 Fee Simple Listed By: Maui Lifestyle Realty LLC

Desirable Upcountry location within walking distance to Makawao Town! This warm, inviting, cozy 3br, 2ba home has beautiful high wood ceilings in the living area with lar...

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1854 Olinda in Makawao/Olinda/Haliimaile

MLS Number: 375619 Bedrooms: 1
Status: PENDING - CONT. TO SHOW Baths: 2.00
Acreage: 5.4400 acres (approx) Interior:1300 sq. ft. (approx)
Price: $1,290,000 Fee Simple Listed By: Island Sotheby's Int'l Rlty(M)

Lovely Olinda. Romantic, private hideaway with expansive views, and incredible privacy in a tranquil, natural setting. The 2 bedroom chalet & gazebo/studio are a bonus to...

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3559 Baldwin in Makawao/Olinda/Haliimaile

MLS Number: 378596 Bedrooms: 2
Status: PENDING - CONT. TO SHOW Baths: 2.00
Acreage: 0.5226 acres (approx) Interior:1040 sq. ft. (approx)
Price: $639,000 Fee Simple Listed By: Trinity Properties, LLC

Everything you need and nothing you don't. The perfect little nook in Makawao Town. Walk in to town, grab a coffee, but enjoy quiet and tranquility at home. Head to the b...

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51 Kealaloa in Makawao/Olinda/Haliimaile

MLS Number: 376907 Bedrooms: 5
Status: ACTIVE Baths: 2.00
Acreage: 0.7775 acres (approx) Interior:1616 sq. ft. (approx)
Price: $596,000 Fee Simple Listed By: BHGRE Valley Isle (P)

Are you looking to live in an established neighborhood in the heart of Upcountry? Located off the main road on a quiet cul-de-sac in the desirable Kealaloa neighborhood,...

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325 Waiahiwi in Makawao/Olinda/Haliimaile

MLS Number: 376128 Bedrooms: 2
Status: ACTIVE Baths: 2.00
Acreage: 151.5700 acres (approx) Interior:3186 sq. ft. (approx)
Price: $7,000,000 Fee Simple Listed By: Island Sotheby's Int'l Rlty(W)

Own a portion of the iconic Piiholo Ranch. This is nearly 150 acres of land, including a 1,700 sq.ft. 2 bed/2 bath home with 4,400 sq. ft. barn, riding arenas, stables an...

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Displaying results 1 - 20 of
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