Makawao/Olinda/Haliimaile Homes under $2.5 million

Makawao/Olinda/Haliimaile Homes under $2.5 million

Nestled in the heart of Maui, the charming community of Makawao, along with its picturesque neighbors Olinda and Haliimaile, offers a unique blend of rustic charm and modern convenience. Known for its rich paniolo (cowboy) heritage, this vibrant area is steeped in history and surrounded by breathtaking natural beauty. With lush green hills, scenic views of the Pacific Ocean, and a temperate climate, it’s no wonder that residents and visitors alike fall in love with the enchanting atmosphere.

Makawao is characterized by its quaint, small-town vibe, featuring art galleries, boutique shops, and delightful eateries that celebrate local flavors. The community is also home to an array of outdoor activities, from hiking trails that wind through the lush landscapes of the nearby Haleakala National Park to horseback riding experiences that pay homage to its ranching roots.

For those seeking a home in this idyllic setting, there are a variety of properties available under $2.5 million. Whether you’re looking for a cozy cottage with a garden view, a spacious family home with ample outdoor space, or a luxurious retreat with panoramic vistas, the Makawao/Olinda/Haliimaile area has something for everyone.

Living here means embracing a lifestyle filled with community spirit, outdoor adventures, and a connection to nature. With its stunning landscapes and welcoming atmosphere, this region truly embodies the essence of island living. Explore your options today and discover the perfect home in this captivating corner of Maui!

Newest Makawao/Olinda/Haliimaile Homes under $2.5 million

845 Puapana Pl, Makawao
$808,000
2 Beds ⋅ 1 Baths ⋅ 411092 MLS ⋅ Fee Simple Tenure
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 other queen) incineration toilet, 35,000 gallon water catchment, spacious covered deck area approx. 12 ft. X 24 ft. deck approx. 20 ft X 30 ft. detached shed with deck approx.12X12. All Deck is similar to Trek. Fully insulated and weather protection. Mini-Split A/C and Heat. Washer/dryer and new on demand hot water heater. Tiny home built byTiny Mountain Homes in Oregon 2021. Electric connected to property. Private drive, avocado tree, jacaranda and other beautiful plants, a must see.

845 Puapana Pl, Makawao

Listing courtesy of Chris Bakeman Realty LLC.

1018 Ulele St Unit Unit B, Makawao
$744,000
2 Beds ⋅ 1 Baths ⋅ 411070 MLS ⋅ Fee Simple Tenure
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 bright, open-concept kitchen and living area creates a welcoming atmosphere, with partial ocean views from both spaces. Updated vinyl flooring, kitchen appliances purchased in 2025, and a washer and dryer purchased in 2026 add to the home’s appeal. Enjoy the added convenience of a 200 sq. ft. carport, providing covered outdoor space, along with an open yard offering room to enjoy the fresh Upcountry air. Located just minutes from Makawao town’s shopping, dining, schools, and parks, this move-in-ready cottage combines everyday convenience with the cooler climate and relaxed lifestyle of Upcountry Maui. This is Unit B of a two-unit CPR. Don’t miss your chance to make this exceptional property your own—schedule a showing today!

1018 Ulele St Unit Unit B, Makawao

Listing courtesy of Keller Williams Realty Maui-Ka.

1199 Freitas Pl Pl, Makawao
$1,200,000
3 Beds ⋅ 2 Baths ⋅ 410916 MLS ⋅ Fee Simple Tenure
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 entertainment room, & an additional room that leads to the covered patio. Enjoy the large fenced lot filled with an abundance of fruit trees, established hedge for privacy, & roomy tool shed. The main bath has been beautifully remodeled with custom tile, counter top, & storage. Kitchen boasts new countertops & tile backsplash. The original kitchen sink stainless steel with side boards, not to be missed. Huge 2 car garage with storage, laundry room & bath with furo. Detached cottage is approx. 660 st. ft with its own electric meter and carport. A blank canvas for you to make it your own. Easy to show. This location is close to the Makawao rest., shops, entertainment, famous Komoda Bakery, schools, gyms, and other amenities.

1199 Freitas Pl Pl, Makawao

Listing courtesy of Chris Bakeman Realty LLC.

640 Makawao Ave, Makawao
$1,599,000
4 Beds ⋅ 2 Baths ⋅ 410773 MLS ⋅ Fee Simple Tenure
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 it and open sky in every direction. Cool mornings, usable ground, and a location that needs no explaining to anyone who knows upcountry. The parcel is zoned agricultural and largely open. Room for pasture, orchard, gardens, animals, or equipment, with space left over. A 4 bedroom, 2 bath home sits on the property and is ready to live in now. Makawao town and the shops and restaurants along Baldwin Avenue are minutes away, with Kahului a short drive down the hill. Over two acres fronting Makawao Avenue rarely becomes available, and property held this long tends to sell once and stay put. Come see it in person, since the size and the setting read differently on the ground than they do in photos. Contact your agent to schedule a private showing.

640 Makawao Ave, Makawao

Listing courtesy of Keller Williams Realty Maui-Ka.

1102 Mailuna Pl, Makawao
$1,475,000
3 Beds ⋅ 3 Baths ⋅ 410602 MLS ⋅ Fee Simple Tenure
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 thoughtful design, lush surroundings, private pool, intimate outdoor spaces, and an exceptionally flexible floor plan. The home feels both gracious and wonderfully easy to live in, with a sense of privacy and tranquillity that is increasingly difficult to find. Upstairs, an inviting living room is warmed by a cozy gas fireplace, while expansive windows draw in abundant natural light and frame the verdant surroundings. The kitchen and living spaces open naturally toward the home's vine-draped lanai on the lee side- the Owner's favorite place to gather, dine, and enjoy the sweet views toward Makawao sunsets. The spacious primary suite offers a private retreat, complete with built-in bookshelves and a serene sense of separation from the rest of the home. Downstairs feels like its own private world. Two additional bedrooms and an exceptionally generous second living room create a versatile configuration for guests, extended family, a home office, or live-in relatives. From the bedrooms, step directly onto your private lanai and toward the pool and gardens, creating an effortless connection to the outdoors. Outside, the beautifully landscaped grounds are designed for privacy and enjoyment. A fabulous intimate lap pool and cozy pool pavilion provides a peaceful focal point for this residence. For energy efficiency, the property is also equipped with 32 photovoltaic panels. The location is equally compelling. Enjoy the charm of Makawao town within walking distance, while Kahului and Baldwin Beach are approximately 20 minutes away. Here, thoughtful architecture, lush grounds, privacy, flexible living spaces, and an enviable Upcountry setting come together in a truly special property. A distinctive home with wonderful possibilities.

1102 Mailuna Pl, Makawao

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

30 Pahaa Pl, Makawao
$1,095,000
4 Beds ⋅ 3 Baths ⋅ 410550 MLS ⋅ Fee Simple Tenure
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. Situated on approximately ¼ acre, this private property offers generous indoor and outdoor living, a flexible floor plan, mature landscaping and numerous recent improvements, including nearly 1000 additional square feet of bonus living space with beautiful ocean views from the backyard and Haleakala views from the front yard. The bright and refreshed main residence features new interior paint and numerous updated doors, fixtures and finishes. The well-appointed kitchen offers cherry cabinetry, granite countertops, stainless steel appliances and gas cooking. Photovoltaic solar panels, solar hot water and seven split-system A/C units add comfort and energy efficiency throughout the property. A converted garage now serves as a spacious bonus room/gym with Murphy bed, offering flexible possibilities for recreation, work or guests. The attached nohana space has also been substantially upgraded with a remodeled kitchen and bathroom, stacked washer/dryer and an enclosed former porch creating additional usable space. Outside, a newly stained deck and patio overlook the spacious, fully fenced yard shaded by mature fruit trees, with two sheds providing additional storage and garden space. Multiple avocado trees, fig, citrus, banana, lime, dragonfruit, pineapple and a bountiful spice garden offers options for additional income, or just to enjoy the bounties of island living. Conveniently located near Pukalani and Makawao shopping, schools, parks and Upcountry amenities, and approximately 15 minutes from Kahului and the North Shore, 30 Paha‘a Place offers the space, flexibility and relaxed lifestyle that make Upcountry Maui living so special. Private. Updated. Versatile. Energy-conscious. And ready for its next chapter.

30 Pahaa Pl, Makawao

Listing courtesy of Keller Williams Realty Maui-Ka.

3566 Kalua Pl, Makawao
$750,000
4 Beds ⋅ 2 Baths ⋅ 410447 MLS ⋅ Fee Simple Tenure
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 the charm of Upcountry living in a well-established neighborhood where neighbors know and care for one another. Situated on a quiet, private street, the home provides a peaceful setting while remaining close to everyday conveniences. This longtime family home has been expanded over the years, creating additional living space. The improvements were completed without permits, and county records do not reflect the current configuration. Buyers are advised to conduct their own due diligence regarding the property's condition, improvements, and county records. Property is served by county water, a cesspool, and county trash service. Open House: Sunday, August 9, from 10:00 AM to 2:00 PM. Come explore the possibilities this centrally located Makawao home has to offer!

3566 Kalua Pl, Makawao

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

305 Iini Way, Makawao
$1,333,333
4 Beds ⋅ 4 Baths ⋅ 410393 MLS ⋅ Fee Simple Tenure
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 roof conveniently located in Makawao. The well-designed floor plan places the spacious living and dining areas at the center of the home, separating two bedrooms on each side to provide both privacy and functionality. The remodeled kitchen features custom cabinetry, a gas range, and a convenient pass-through window to the outdoor dining area, making entertaining a breeze. This versatile space can also serve as a covered carport when desired. Recent upgrades include luxury vinyl plank flooring, split A/C throughout, instant water heater shared by primary bath and 2nd bedroom bath, and numerous thoughtful updates throughout. Beyond the dining area, the covered pavilion and expansive interlocking deck tile patio create an inviting outdoor retreat with plenty of room for relaxing, entertaining, or enjoying Makawao's comfortable Upcountry climate. 305 Iini Way—a home you'll be longing to come home to.

305 Iini Way, Makawao

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

156 Alaluana Rd, Makawao
$1,650,000
2 Beds ⋅ 2 Baths ⋅ 410267 MLS ⋅ Fee Simple Tenure
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 property is a custom-crafted 2-bedroom bamboo home that blends natural beauty, sustainability, and timeless design. Bamboo is prized around the world for its strength, warmth, and renewable qualities, creating a truly unique living environment. A long ribbon driveway welcomes you to the home, where custom craftsmanship and thoughtful details create living spaces with views of the surrounding countryside and the ocean beyond. The property is well equipped with abundant potable water supplied by three 30,000-gallon water storage tanks, providing ample capacity for the home and agricultural uses. A spacious barn adds versatility, featuring a separate apartment and a large workshop currently used for woodworking. Whether you're looking for space to farm, create, work, or simply enjoy the Upcountry lifestyle, this property offers endless possibilities. An opportunity to own a private Maui property where craftsmanship, sustainability, and quiet country living come together. So peaceful!

156 Alaluana Rd, Makawao

Listing courtesy of Coldwell Banker Island Prop(P).

37 Pukiki Pl Unit B, Makawao
$999,000
2 Beds ⋅ 1 Baths ⋅ 410243 MLS ⋅ Fee Simple Tenure
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 located in one of Maui’s most sought-after microclimates, where cool trade winds, beautiful ocean and North Shore views, and a serene setting create an exceptional place to call home. Thoughtfully designed with an emphasis on indoor-outdoor living, the spacious 253 square foot covered lanai and enclosed carport provide the perfect space for entertaining, dining, or simply unwinding while enjoying the surrounding beauty. Recently CPR’d and complete with its own septic system, this move-in-ready home offers the ideal blend of comfort, functionality, and low-maintenance living. The fully fenced yard provides ample space for pets, gardening, and enjoying the Upcountry lifestyle, with room to create your own private oasis. Conveniently located just minutes from Makawao Town’s charming boutiques, local restaurants, cafés, and renowned art galleries, you’ll also appreciate easy access to Seabury Hall, Carden Academy, Montessori School of Maui, and many of the island’s top public and private schools. If you’ve been searching for the “right-sized” Upcountry home that combines privacy, convenience, breathtaking views, and a true sense of tranquility, 37 Pukiki Place delivers. This is a CPR Residential condo Unit #B.

37 Pukiki Pl Unit B, Makawao

Listing courtesy of Coldwell Banker Island Prop(S).

35 Pukiki Pl Unit A, Makawao
$1,350,000
6 Beds ⋅ 4 Baths ⋅ 410242 MLS ⋅ Fee Simple Tenure
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 microclimates. Recently renovated, this expansive 6 bedroom, 4 bathroom residence captures refreshing trade winds, beautiful ocean and North Shore views, and the privacy and tranquility that make this area so special. This two-story home’s greatest asset is its remarkably versatile floor plan, thoughtfully designed to provide exceptional separation of living spaces, with separate entrances for both levels, that feels like getting two homes for the price of one. Whether accommodating multigenerational living, extended family, long-term guests, a private home office, creative studio, fitness space, or simply providing room for everyone to spread out, the possibilities are endless. Indoor and outdoor spaces blend seamlessly, creating an inviting setting for entertaining, gathering with family and friends, or enjoying peaceful mornings and cool Upcountry evenings surrounded by nature. The fenced yard offers ample room for pets, gardening, outdoor recreation, or creating your own private sanctuary. Recently CPR’d and move-in ready, this property offers flexibility rarely found in today’s market. Conveniently located just minutes from Makawao Town’s acclaimed restaurants, cafes, boutiques, and renowned art galleries, while also providing easy access to Seabury Hall, Carden Academy, Montessori School of Maui, and many of the island’s premier public and private schools. Whether you’re seeking room to grow, a flexible layout to fit your evolving lifestyle, or simply a peaceful retreat with room for everyone, 35 Pukiki Place delivers an exceptional combination of space, comfort, privacy, and convenience in one of Upcountry Maui’s most coveted locations. Experience the side of Maui where life slows down. This is a CPR Residential condo Unit #A.

35 Pukiki Pl Unit A, Makawao

Listing courtesy of Coldwell Banker Island Prop(S).

15 Olinda Rd, Makawao
$2,350,000
5 Beds ⋅ 4 Baths ⋅ 409724 MLS ⋅ Fee Simple Tenure
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 and long-term upside. There are 5 one bedroom units, and 3 two bedroom units. Situated on just over half an acre, the property features four separate structures with a total of eight tenant-occupied units, creating an income-producing compound in one of Upcountry Maui’s most desirable locations. Tenants enjoy dedicated parking, on-site laundry, and the convenience of being moments from Makawao’s shops, restaurants, galleries, and local charm. Numerous improvements have already been completed, making this an attractive opportunity for an investor looking to step into an established rental property with immediate income potential. The property also has 3 water meters. Listing includes photos of one of the 8 units. A truly one-of-a-kind upcountry investment property.

15 Olinda Rd, Makawao

Listing courtesy of eXp Realty.

Start Your Search

How much is your home worth?

Get instant property value now!