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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 27
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2372 Baldwin in Makawao/Olinda/Haliimaile

MLS Number: 371007 Bedrooms: 5
Status: ACTIVE Baths: 5.50
Acreage: 35.0000 acres (approx) Interior:5210 sq. ft. (approx)
Price: $12,800,000 Fee Simple Listed By: Coldwell Banker Island Prop(P)

Welcome to 2372 Baldwin Avenue, the legendary Plantation Ranch of Paholei. In 1889, Paholei was known as the Haliimaile Plantation, eventually to become a pivotal part of...

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48 Ohaoha in Makawao/Olinda/Haliimaile

MLS Number: 373947 Bedrooms: 4
Status: ACTIVE Baths: 3.00
Acreage: 2.0600 acres (approx) Interior:4653 sq. ft. (approx)
Price: $2,250,000 Fee Simple Listed By: Coldwell Banker Island Prop(P)

Built in 2006, designed for gatherings to relax and take in the wide views of West Maui Mountains and the ocean views from west to east. An area held closely by the Baldw...

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1860 Olinda in Makawao/Olinda/Haliimaile

MLS Number: 374010 Bedrooms: 5
Status: ACTIVE Baths: 4.50
Acreage: 2.6333 acres (approx) Interior:3992 sq. ft. (approx)
Price: $3,100,000 Fee Simple Listed By: Tim Gardner Realty

Located in magical Olinda, high above Historic Makawao Town, this estate was once named "Angel's Nest", and for good reason. When you are in the "Nest", you feel like y...

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3077 Baldwin in Makawao/Olinda/Haliimaile

MLS Number: 368123 Bedrooms: 3
Status: ACTIVE Baths: 4.00
Acreage: 6.6300 acres (approx) Interior:2968 sq. ft. (approx)
Price: $3,800,000 Fee Simple Listed By: Hawaii Life RealEstate Brokers

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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3035 Baldwin in Makawao/Olinda/Haliimaile

MLS Number: 372260 Bedrooms: 4
Status: PENDING - CONT. TO SHOW Baths: 2.50
Acreage: 70.7520 acres (approx) Interior:2966 sq. ft. (approx)
Price: $6,800,000 Fee Simple Listed By: The Wailea Group LLC

This recreational dream estate is one of the most exceptionally rare properties in all of Hawaii. Spanning a lush 70-acres, this turn-key property features a stunning cus...

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220 Ohaoha in Makawao/Olinda/Haliimaile

MLS Number: 374091 Bedrooms: 3
Status: ACTIVE Baths: 4.50
Acreage: 2.0760 acres (approx) Interior:2739 sq. ft. (approx)
Price: $2,395,000 Fee Simple Listed By: Island Sotheby's Int'l Rlty(M)

Discover resort style living merely minutes from Makawao Town, Hali’imaile and some of Upcountry’s finest schools, with Pa’ia and the North Shore beaches a short dr...

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16 Ehu in Makawao/Olinda/Haliimaile

MLS Number: 374193 Bedrooms: 4
Status: ACTIVE Baths: 2.00
Acreage: 2.0906 acres (approx) Interior:2496 sq. ft. (approx)
Price: $850,000 Fee Simple Listed By: FlatList.com

This beautiful 2 story 4 bedroom home has an amazing view that also comes with a 200 square feet work studio. With over 2 acres of privately owned land you will have the ...

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1420 PIIHOLO in Makawao/Olinda/Haliimaile

MLS Number: 373665 Bedrooms: 4
Status: ACTIVE Baths: 3.00
Acreage: 1.3790 acres (approx) Interior:2240 sq. ft. (approx)
Price: $1,275,000 Fee Simple Listed By: T & C Realty

Charming, Spacious and extremely comfortable Upcountry Home with 2 additional separate detached cottages for extended Family or income potential. That's a total of 3 unit...

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1565 Makawao in Makawao/Olinda/Haliimaile

MLS Number: 374194 Bedrooms: 4
Status: ACTIVE Baths: 2.50
Acreage: 4.8800 acres (approx) Interior:2084 sq. ft. (approx)
Price: $997,000 Fee Simple Listed By: C21Al Fine Homes & Estates (Ka)

Your exclusive “Waterfall Home & Estate” just moments to Makawao town on Maui’s North Shore. Graced with nearly 5 acres of tranquil land, bordering an awe-inspiring...

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2625 Olinda in Makawao/Olinda/Haliimaile

MLS Number: 372600 Bedrooms: 3
Status: ACTIVE Baths: 2.50
Acreage: 4.1730 acres (approx) Interior:1982 sq. ft. (approx)
Price: $1,125,000 Fee Simple Listed By: Hawaii Life RealEstate Brokers

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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454 Kaiaulu in Makawao/Olinda/Haliimaile

MLS Number: 373948 Bedrooms: 4
Status: PENDING - CONT. TO SHOW Baths: 3.00
Acreage: 0.6630 acres (approx) Interior:1778 sq. ft. (approx)
Price: $742,000 Fee Simple Listed By: Island Sotheby's Int'l Rlty(M)

PRIDE OF OWNERSHIP is evident in this lovely, versatile home in Maui Uplands! No surprises here, this home is totally permitted. The original owners added a 4th bedroom s...

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21 Kealaloa in Makawao/Olinda/Haliimaile

MLS Number: 373999 Bedrooms: 3
Status: ACTIVE Baths: 2.00
Acreage: 1.2540 acres (approx) Interior:1656 sq. ft. (approx)
Price: $459,000 Fee Simple Listed By: Green Realty Group

This older 3-br/2-ba home in an established neighborhood can be transformed into a beautiful home with your creativity. It can possibly be used as 5 bedrooms with its pre...

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55 Makalani in Makawao/Olinda/Haliimaile

MLS Number: 371143 Bedrooms: 3
Status: ACTIVE Baths: 2.00
Acreage: 0.1921 acres (approx) Interior:1652 sq. ft. (approx)
Price: $675,000 Fee Simple Listed By: C21Al Fine Homes & Estates (W)

This home has great bones and great location. Walking distance to town, close to schools and bus line. There is a wonderful cottage set behind and below the main house. T...

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1690 Piiholo in Makawao/Olinda/Haliimaile

MLS Number: 371431 Bedrooms: 2
Status: PENDING - CONT. TO SHOW Baths: 2.00
Acreage: 7.9980 acres (approx) Interior:1568 sq. ft. (approx)
Price: $1,294,000 Fee Simple Listed By: Island Sotheby's Int'l Rlty(M)

Pure Olinda. Ultimate privacy, tranquility and seclusion. Amazing setting, enchanting sunsets and inspiring views which embrace and nourish your spirit… and only 3 mil...

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1123 Puana in Makawao/Olinda/Haliimaile

MLS Number: 374046 Bedrooms: 3
Status: PENDING - CONT. TO SHOW Baths: 3.00
Acreage: 0.1465 acres (approx) Interior:1440 sq. ft. (approx)
Price: $615,000 Fee Simple Listed By: Delmore Realty

Wouldn't it be fun to live just around the corner from Makawao Steak House, Komoda's Bakery and other Makawao town shops & restaurants, as well as Makawao Elementary? It'...

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0 Olinda in Makawao/Olinda/Haliimaile

MLS Number: 367214 Bedrooms: 1
Status: ACTIVE Baths: 2.00
Acreage: 5.4400 acres (approx) Interior:1300 sq. ft. (approx)
Price: $1,560,000 Fee Simple Listed By: Island Sotheby's Int'l Rlty(M)

Romantic Private Hideaway with Expansive Views Rare combination of both incredible views and privacy. Olinda custom home, cottage & gazebo on 5+ acres. Easily expandab...

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222 N Makaleha in Makawao/Olinda/Haliimaile

MLS Number: 373712 Bedrooms: 3
Status: PENDING - CONT. TO SHOW Baths: 2.00
Acreage: 0.1508 acres (approx) Interior:1284 sq. ft. (approx)
Price: $690,000 Fee Simple Listed By: Island Sotheby's Int'l Rlty(M)

Brand spanking new! Be the first to live in this beautiful, single-level, 3-bedroom, 2-bath home with 2 covered lanais and attached garage. This home was just recently ...

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74 Leie in Makawao/Olinda/Haliimaile

MLS Number: 374163 Bedrooms: 3
Status: PENDING - CONT. TO SHOW Baths: 1.00
Acreage: 0.1894 acres (approx) Interior:1036 sq. ft. (approx)
Price: $365,000 Fee Simple Listed By: Maui Tropical Realty

Hailiimaile fixer-upper with lots potential. Current set up as a 4 bedroom 2 bath with very large carport and storage area. Lots of fruit bearing trees Do a drive by FI...

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15 Laie Iki in Makawao/Olinda/Haliimaile

MLS Number: 373321 Bedrooms: 3
Status: PENDING - CONT. TO SHOW Baths: 2.00
Acreage: 0.2445 acres (approx) Interior:1008 sq. ft. (approx)
Price: $699,700 Fee Simple Listed By: Island Sotheby's Int'l Rlty(M)

Newly remodeled 3 bed 2 bath main home with a 2 bed 1 bath cottage. Quiet and private location yet very convenient. Some ocean views and all brand new stainless appliance...

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720 Kekona in Makawao/Olinda/Haliimaile

MLS Number: 373890 Bedrooms: 3
Status: PENDING - CONT. TO SHOW Baths: 1.00
Acreage: 0.1676 acres (approx) Interior:988 sq. ft. (approx)
Price: $549,000 Fee Simple Listed By: Island Sotheby's Int'l Rlty(M)

Perfect starter home…centrally located in Makawao on a cul d sac street. This home has loads to offer! Property offers gated access and fully fenced in yard. It is th...

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Displaying results 1 - 20 of
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