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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 21
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2372 Baldwin in Makawao/Olinda/Haliimaile

MLS Number: 367129 Bedrooms: 5
Status: ACTIVE Baths: 5.50
Acreage: 34.9880 acres (approx) Interior:5210 sq. ft. (approx)
Price: $12,800,000 Fee Simple Listed By: Elite Pacific Properties, LLC

Considered to be one of the top equestrian estates in all of Hawaii. This approximately 35 acre estate has been a part of Maui's history for over 100 years. The timeless ...

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3035 Baldwin in Makawao/Olinda/Haliimaile

MLS Number: 365753 Bedrooms: 4
Status: PENDING - CONT. TO SHOW Baths: 2.50
Acreage: 70.7520 acres (approx) Interior:2966 sq. ft. (approx)
Price: $6,900,000 Fee Simple Listed By: Island Sotheby's Int'l Rlty(M)

Extraordinary Upcountry There are only a few properties on Maui that capture and embrace Maui’s diverse beauty, tranquility and complete privacy while providing a u...

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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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2210 Olinda in Makawao/Olinda/Haliimaile

MLS Number: 365132 Bedrooms: 3
Status: ACTIVE Baths: 2.00
Acreage: 39.7600 acres (approx) Interior:3479 sq. ft. (approx)
Price: $3,500,000 Fee Simple Listed By: Wailea Realty Corp

This beautiful, nearly 40 acre ranch is in upper Olinda in the Eucalyptus tree country. It is bordered on the upper length of the property by the Waihou Spring Forest Res...

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1860 Olinda in Makawao/Olinda/Haliimaile

MLS Number: 369262 Bedrooms: 5
Status: ACTIVE Baths: 4.50
Acreage: 2.6333 acres (approx) Interior:3992 sq. ft. (approx)
Price: $2,593,000 Fee Simple Listed By: Maui Home and Life

Captivating views astound from every room of this classic contemporary luxury family home. Featuring a fantastic floor plan with a grand master suite (inclusive of separa...

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1690 Piiholo in Makawao/Olinda/Haliimaile

MLS Number: 368626 Bedrooms: 1
Status: ACTIVE Baths: 2.00
Acreage: 8.0000 acres (approx) Interior:1609 sq. ft. (approx)
Price: $2,100,000 Fee Simple Listed By: Big Wave Realty LLC

Private, Serene, Horticulturist Heaven, Garden of Eatin, 8 acres in upcountry Olinda. Elevation aprox 2900'. If you have been dreaming of living the good life, of growing...

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69 Aulii in Makawao/Olinda/Haliimaile

MLS Number: 368509 Bedrooms: 4
Status: ACTIVE Baths: 3.00
Acreage: 2.0025 acres (approx) Interior:3600 sq. ft. (approx)
Price: $2,075,000 Fee Simple Listed By: Island Sotheby's Int'l Rlty(W)

This gated estate or family compound is spread over one of the most functional 2-acre ocean and mountain view parcels on island. Designed for the active lifestyle, there...

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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 expand...

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960 Olinda in Makawao/Olinda/Haliimaile

MLS Number: 369341 Bedrooms: 3
Status: ACTIVE Baths: 3.00
Acreage: 1.5000 acres (approx) Interior:3720 sq. ft. (approx)
Price: $1,295,000 Fee Simple Listed By: Island Sotheby's Int'l Rlty(M)

Close to Seabury--Ocean-View Home, Cottage, Pool on 1.5 acres. Less than one mile above Seabury Hall, this expansive 3 bedroom/3 bath custom home and 2 bed/1 bath cottag...

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70 Ahualani in Makawao/Olinda/Haliimaile

MLS Number: 367821 Bedrooms: 4
Status: PENDING - CONT. TO SHOW Baths: 2.00
Acreage: 2.1000 acres (approx) Interior:2400 sq. ft. (approx)
Price: $997,000 Fee Simple Listed By: Coldwell Banker Island Prop(Ka)

Located in the highly desired district referred to as Upcountry Maui, this "EQUINE MODIFIED" property offers much to any potential buyer. Situated on 2 acres of land, cu...

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2611 Olinda in Makawao/Olinda/Haliimaile

MLS Number: 368831 Bedrooms: 3
Status: ACTIVE Baths: 2.00
Acreage: 1.5640 acres (approx) Interior:2360 sq. ft. (approx)
Price: $969,000 Fee Simple Listed By: Island Sotheby's Int'l Rlty(M)

Olinda Magic… Views, views, VIEWS! Lovely 3 bed/2.5 bath pole house with amazing vistas from both the marvelous great room, ideal for entertaining, and the oversized ma...

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620 Laie in Makawao/Olinda/Haliimaile

MLS Number: 368053 Bedrooms: 4
Status: PENDING - CONT. TO SHOW Baths: 3.00
Acreage: 0.4115 acres (approx) Interior:2014 sq. ft. (approx)
Price: $840,000 Fee Simple Listed By: BHGRE Valley Isle (P)

Reminiscent of a bygone era, the charm of this kama'aina home is timeless. A spacious, well-constructed heritage home of this caliber in Makawao is truly a rare treasure...

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495 Kaiaulu in Makawao/Olinda/Haliimaile

MLS Number: 369060 Bedrooms: 3
Status: ACTIVE Baths: 2.00
Acreage: 0.5000 acres (approx) Interior:2026 sq. ft. (approx)
Price: $799,000 Fee Simple Listed By: Equity One Real Estate Inc (P)

Here's your chance to become a member of the Maui Uplands community! Situated on a half-acre parcel are a roomy 3 bedrooms/2 baths main house and a one bedroom/one bath ...

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1811 Piiholo in Makawao/Olinda/Haliimaile

MLS Number: 367729 Bedrooms: 2
Status: PENDING - CONT. TO SHOW Baths: 1.00
Acreage: 1.3500 acres (approx) Interior:756 sq. ft. (approx)
Price: $699,000 Fee Simple Listed By: Big Wave Realty LLC

Step back to 1929 upcountry Maui! Painstakingly renovated historic cottage on a 1.35 acre Ag lot. This is one of the most unique and charming offerings on Maui. At 29...

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34 Makalani in Makawao/Olinda/Haliimaile

MLS Number: 368760 Bedrooms: 3
Status: ACTIVE Baths: 2.00
Acreage: 0.1520 acres (approx) Interior:1241 sq. ft. (approx)
Price: $680,000 Fee Simple Listed By: Millennium Realty, Inc.

Charming Upcountry Home. Located in a quiet area in Makawao. House is well kept and has a well cared for yard. There is a carport in the front which connects to larger p...

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1090 Aala in Makawao/Olinda/Haliimaile

MLS Number: 367046 Bedrooms: 3
Status: PENDING - CONT. TO SHOW Baths: 1.00
Acreage: 0.2848 acres (approx) Interior:864 sq. ft. (approx)
Price: $647,000 Fee Simple Listed By: Island Sotheby's Int'l Rlty(M)

Great location with amazing views. Older house and cottage on a charming dead end street on the outskirts of Makawao Town. These properties do not come on the market ofte...

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155 Kuono in Makawao/Olinda/Haliimaile

MLS Number: 369051 Bedrooms: 3
Status: PENDING - CONT. TO SHOW Baths: 2.00
Acreage: 0.1464 acres (approx) Interior:2202 sq. ft. (approx)
Price: $625,000 Fee Simple Listed By: Maui Real Estate Advisors LLC

A quiet Upcountry location in Makawao Town, which is known for its charming shops, restaurants and comfortable climate. The property is on a quiet cul-de-sac and is fully...

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1081 Puana in Makawao/Olinda/Haliimaile

MLS Number: 369225 Bedrooms: 3
Status: ACTIVE Baths: 2.00
Acreage: 0.1569 acres (approx) Interior:1108 sq. ft. (approx)
Price: $575,000 Fee Simple Listed By: Help-U-Sell Honolulu Prop.

CONVENIENT COUNTRY LIVING! UPDATED home located on a QUIET CORNER LOT & just a SHORT STROLL to shopping, dining and school. FLOWING floorplan features Master br with PRI...

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746 Ponoi in Makawao/Olinda/Haliimaile

MLS Number: 368571 Bedrooms: 3
Status: PENDING - CONT. TO SHOW Baths: 1.25
Acreage: 1.2247 acres (approx) Interior:800 sq. ft. (approx)
Price: $440,000 Fee Simple Listed By: Island Sotheby's Int'l Rlty(M)

The charm of a South Hampton cottage nestled in one of Makawao’s most appealing enclaves, this sweet home is set amongst a lovingly landscaped yard complete with an art...

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104 Leie in Makawao/Olinda/Haliimaile

MLS Number: 368262 Bedrooms: 3
Status: PENDING - CONT. TO SHOW Baths: 1.00
Acreage: 0.2066 acres (approx) Interior:906 sq. ft. (approx)
Price: $395,000 Fee Simple Listed By: NextHome Pacific Properties

Nestled in Haliimaile is an opportunity to revive or possibly redesign a home that has roots in the neighborhood. Originally built in 1938 the house features a 3 bedroom,...

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