Makawao/Olinda/Haliimaile Homes under $2.5 million

Welcome to the enchanting neighborhoods of Makawao, Olinda, and Haliimaile, nestled in the lush hills of Maui, Hawaii. This charming region is a hidden gem that beautifully blends the serene ambiance of rural living with the vibrant spirit of island culture. Known for its cooler climate and stunning vistas, these neighborhoods offer a perfect escape from the hustle and bustle of coastal life.

Makawao, once a bustling ranching town, retains its historical charm with art galleries, boutique shops, and delightful eateries that reflect the rich heritage of the area. Stroll through the streets and you’ll discover a vibrant community that celebrates local artists and craftspeople. The nearby Olinda area is renowned for its breathtaking views, lush greenery, and tranquil atmosphere, making it a perfect spot for those seeking a peaceful retreat. Haliimaile, with its unique blend of agricultural charm and residential comfort, invites you to experience the beauty of rural Maui living.

For those looking to invest in this picturesque locale, there are beautiful homes available under $2.5 million. These properties offer a range of styles, from charming plantation-style houses to modern builds, all set against the backdrop of Maui's stunning landscapes. With ample space for gardens and outdoor activities, these homes are perfect for families, retirees, or anyone seeking a slice of paradise.

Embrace the Maui lifestyle in Makawao, Olinda, and Haliimaile, where community spirit meets natural beauty, and your dream home awaits!

Newest Makawao/Olinda/Haliimaile Homes under $2.5 million

845 Puapana Pl, Makawao $808,000

Makawao Oasis, over 8800 sq. ft. lot, Haleakala View, Bananas galore, on a flag lot. Tiny home that lives large, approx. 400 sq. ft. 2 Loft bedrooms, (one king size, the...

ACTIVE Status
2 Beds
1 Baths
411092 MLS
Fee Simple Tenure

Courtesy of Chris Bakeman Realty LLC

Listing courtesy of Chris Bakeman Realty LLC.

1018 Ulele St Unit Unit B, Makawao image

1018 Ulele St Unit Unit B, Makawao $744,000

Upcountry Cottage with Ocean Views & Open Yard This freestanding 2-bedroom, 1-bath cottage offers approximately 600 sq. ft. of living space and was renovated in 2023. The...

ACTIVE Status
2 Beds
1 Baths
411070 MLS
Fee Simple Tenure

Courtesy of Keller Williams Realty Maui-Ka

Listing courtesy of Keller Williams Realty Maui-Ka.

1199 Freitas Pl Pl, Makawao $1,200,000

Up country living at its best downtown Makawao. Lightfilled 3 bed, 2 bath one story home, new vinyl windows throughout. Expansive living room that moves into a large e...

ACTIVE Status
3 Beds
2 Baths
410916 MLS
Fee Simple Tenure

Courtesy of Chris Bakeman Realty LLC

Listing courtesy of Chris Bakeman Realty LLC.

640 Makawao Ave, Makawao $1,549,000 ▼

Over two acres on Makawao Avenue, held by the same owners for generations. The property sits up on a rise in the band between Pukalani and Makawao, with Haleakala above i...

ACTIVE Status
4 Beds
2 Baths
410773 MLS
Fee Simple Tenure

Courtesy of Keller Williams Realty Maui-Ka

Listing courtesy of Keller Williams Realty Maui-Ka.

1102 Mailuna Pl, Makawao $1,475,000 ▼

Tucked privately at the top of a cul-de-sac, this beautifully appointed 3-bedroom, 3-bath home plus office is a Makawao residence that offers a rare combination of thoug...

ACTIVE Status
3 Beds
3 Baths
410602 MLS
Fee Simple Tenure

Courtesy of Equity One Real Estate Inc (P)

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

30 Pahaa Pl, Makawao $1,095,000 ▼

Welcome to 30 Paha‘a Place, a beautifully updated and exceptionally versatile Upcountry Maui home tucked away on a flag lot at the end of a quiet cul-de-sac in Pukalani. ...

ACTIVE Status
4 Beds
3 Baths
410550 MLS
Fee Simple Tenure

Courtesy of Keller Williams Realty Maui-Ka

Listing courtesy of Keller Williams Realty Maui-Ka.

3566 Kalua Pl, Makawao $750,000 ▼

Warm 4-bedroom, 2-bath home in the heart of Makawao! Conveniently located within walking distance to schools, parks, shopping, and local restaurants, this property offers...

ACTIVE Status
4 Beds
2 Baths
410447 MLS
Fee Simple Tenure

Courtesy of Tri-Isle Rlty & Dev Co Inc

Listing courtesy of Tri-Isle Rlty & Dev Co Inc.

305 Iini Way, Makawao $1,333,333 ▼

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 r...

ACTIVE Status
4 Beds
4 Baths
410393 MLS
Fee Simple Tenure

Courtesy of Equity One Real Estate Inc (M)

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

156 Alaluana Rd, Makawao $1,650,000

Follow the country road to the very top of Piiholo Road, where peaceful Upcountry living, privacy, and breathtaking surroundings await. Nestled on this exceptional 3 Acre...

ACTIVE Status
2 Beds
2 Baths
410267 MLS
Fee Simple Tenure

Courtesy of Coldwell Banker Island Prop(P)

Listing courtesy of Coldwell Banker Island Prop(P).

37 Pukiki Pl Unit B, Makawao $999,000

Nestled on a private road, 37 Pukiki Place offers the peace, privacy, and tranquility that define Upcountry Maui living. This recently renovated single-level residence is...

ACTIVE Status
2 Beds
1 Baths
410243 MLS
Fee Simple Tenure

Courtesy of Coldwell Banker Island Prop(S)

Listing courtesy of Coldwell Banker Island Prop(S).

35 Pukiki Pl Unit A, Makawao $1,350,000 ▼

Tucked away on a peaceful private road, 35 Pukiki Place presents a rare opportunity to enjoy the best of Upcountry Maui living in one of the island’s most desirable micro...

ACTIVE Status
6 Beds
4 Baths
410242 MLS
Fee Simple Tenure

Courtesy of Coldwell Banker Island Prop(S)

Listing courtesy of Coldwell Banker Island Prop(S).

15 Olinda Rd, Makawao $2,350,000 ▼

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 an...

ACTIVE Status
5 Beds
4 Baths
409724 MLS
Fee Simple Tenure