Refine Search
Sort by
1423 Olinda Rd, Makawao
$2,500,000
3 Beds ⋅ 2 Baths ⋅ 409998 MLS ⋅ Fee Simple Tenure
Spanning 19.5 acres of rolling countryside on coveted Olinda Road, this remarkable Upcountry Maui property feels like a step back to a simpler time. Framed by expansive open land, mature trees, and the cool elevations of Olinda, the property embodies the charm and character of Maui’s ranching heritage while offering endless possibilities for its next chapter. At its heart sits a classic plantation-style homestead, rich with history and timeless appeal. Whether thoughtfully restored, expanded, or reimagined, the home provides a wonderful foundation for creating a legacy estate, working farm, or peaceful country retreat. As one wanders the grounds, you'll discover mature landscaping, established avocado and fruit trees, and a landscape that has been lovingly cultivated over the years. The land itself is both beautiful and functional, offering ample space for agriculture, animals, gardens, or simply enjoying the privacy and serenity of country living. Complementing the property are a spacious five-car carport, workshop, and agricultural studio, providing flexibility for ranching operations, equipment storage, creative pursuits, or entrepreneurial ventures. Surrounded by panoramic Upcountry beauty and conveniently located within one of Maui's most desirable locations, this property offers a rare opportunity to embrace and live Maui’s island lifestyle.

1423 Olinda Rd, Makawao

Listing courtesy of Island Sotheby's International Realty(M).

1365 Piiholo Rd, Makawao
$1,800,000
3 Beds ⋅ 2 Baths ⋅ 406954 MLS ⋅ Fee Simple Tenure
Discover tranquility and ultimate privacy at this exceptional Upcountry Maui estate. Nestled on the slopes of Haleakala and bordered by a lush gulch, this 3,433 sqft residence and detached cottage are set on two sprawling acres, creating a serene personal retreat. Step into the main home and you will be greeted by an inviting atmosphere. With soaring vaulted ceilings and large picture windows that perfectly frame the expansive ocean views, you will feel like you have nowhere else to be. The recently remodeled kitchen allows you to seamlessly transition to outdoor living on the generous wrap-around lanai, and enjoy breathtaking sunsets year-round. The primary bedroom is on the main floor and the home also has a loft space, perfect for an art studio or yoga space. This home is both expansive, yet cozy, creating a perfect sanctuary. The lower level offers incredible flexibility with a spacious 2-bedroom, 1-bathroom suite, ideal for extended family or guests, as well as a detached cottage that is seperately metered, and has it's own driveway & entrance. Attached to the main home is a 1 car garage as well as a separate 2 car carport along with plenty of space for storage. This is a rare chance to own a versatile and secluded piece of paradise, where the beauty of Upcountry living unfolds around you.

1365 Piiholo Rd, Makawao

Listing courtesy of Keller Williams Realty Maui-Ka.

250 Ulana St, Makawao
$1,690,000
3 Beds ⋅ 2 Baths ⋅ 409264 MLS ⋅ Fee Simple Tenure
Welcome to Maui Uplands, often considered the gem of Makawao. This quality-built 3-bedroom, 2-bath home, along with a separate 2-bedroom, 1-bath detached cottage, is set on beautifully landscaped grounds in one of Upcountry Maui’s most desirable communities. Surrounded by rock walls, fruit trees, and lush tropical plantings, the property is truly a gardener’s delight. Maui Uplands is unique offering underground utilities as well as a community center, pool, and tennis courts—adding to the appeal of this well-loved neighborhood. The home’s charming entrance invites you to linger on the comfortable covered lanai, where you can enjoy views of the garden and stone barbecue area. Inside, the hardwood floors and vaulted ceilings create a warm, airy sense of space. The open-concept kitchen, dining, and living areas, just off the lanai, provide an ideal setting for both entertaining and relaxed island living. The downstairs area offers flexible space suitable for a variety of uses. The 2-bedroom cottage, conveniently located near the property’s entrance, features its own private yard, deck, ample storage, and carport—offering comfort, privacy, and excellent potential for rental income.

250 Ulana St, Makawao

Listing courtesy of REMAX Hawaii Maui.

1733 Piiholo Rd Rd, Makawao
$1,363,950
3 Beds ⋅ 2 Baths ⋅ 408402 MLS ⋅ Fee Simple Tenure
“Pending Continue To Show” Sellers accepting back up offers. Perched in the serene elevations of Upcountry Maui, this property combines breathtaking views with privacy and expansive land, offering exceptional potential for the future. At approximately 3,000 feet above sea level, it enjoys cool, crisp mountain air and a unique natural setting. Consisting of two separate TMKs totaling 1.14 acres. This Lindal Cedar residence offers three bedrooms and two bathrooms on approximately 0.20 acres, along with an adjacent 0.94-acre agricultural parcel that is currently seventh on the County water meter waitlist. Both parcels are being sold together, allowing flexibility for expansion, creative use, or long-term planning. The property embraces its surroundings with vaulted ceilings and large windows that capture views of mature trees and distant ocean scenery. With a wraparound deck, enjoy a warm and inviting interior with a strong connection to the outdoors. Featuring a welcoming open-concept layout, the home is designed for both effortless daily living and seamless entertaining. With the adjacent parcel, the property’s potential is elevated for agricultural use, thoughtful accommodation, or future expansion. Property is Pending continue to show. Sellers are open to taking any backup offers and/or showings.

1733 Piiholo Rd Rd, Makawao

Listing courtesy of Ihu Properties LLC.

1131 Kehau Pl, Makawao
$1,078,000
3 Beds ⋅ 2 Baths ⋅ 410138 MLS ⋅ Fee Simple Tenure
Perched just above Makawao Town, 1131 Kehau Place captures the essence of Upcountry living with sweeping ocean and West Maui Mountain views, cool trade winds, and the convenience of being just minutes from schools, restaurants, shopping, and everyday essentials. This move-in-ready home has been thoughtfully updated with remodeled bathrooms and a refreshed kitchen featuring new stainless steel appliances. Large windows and inviting living spaces frame the stunning views, creating a seamless connection between indoor comfort and Maui’s natural beauty. Situated on a 5-bedroom septic system, the property offers flexibility and future potential. The lower level provides additional space that could serve a variety of uses, including a home office, guest quarters, or future expansion possibilities. Whether you’re enjoying morning coffee while taking in the panoramic views or unwinding at sunset as the West Maui Mountains glow in the distance, this property offers the perfect blend of privacy, convenience, and the Upcountry lifestyle that so many seek. Easy to show and ready for its next chapter.

1131 Kehau Pl, Makawao

Listing courtesy of Compass-W.

34 Alaluana Rd Unit B, Makawao
$1,020,000
1 Beds ⋅ 1 Baths ⋅ 408900 MLS ⋅ Fee Simple Tenure
Upcountry Maui living with many thoughtful upgrades and flexible space! 34 Alaluana Rd #B offers approximately 2,500 sq ft under roof, including a 960 sq ft upper level with 1 bed / 1 bath and open-concept layout. The remodeled kitchen and bath (2022) feature granite and marble countertops, bar seating island, built-in window seat, and a wood-burning fireplace for cozy Makawao evenings. In 2025, the upstairs was further refreshed with refinished wood floors, updated lighting, refinished doors, trim, baseboards, and countertops. Enjoy 704 sq ft of lanai space with a newly extended partially covered patio and freshly repainted deck for improved year-round indoor/outdoor living. The lower level offers over 1,500 sq ft of finished space with separate entrance and tall ceilings, conforming as shop/storage. Since 2022, improvements include added walls and windows for natural light, refinished floors, and additional lighting—creating exceptional flexibility for workshop, creative, or hobby use. Major maintenance items have been addressed, including exterior siding and rot repairs, deck and railing improvements, rebuilt exterior stairs, resealed front wall, and added fencing along Alaluana Road. The landscaped grounds feature mature fruit and ornamental trees (avocado, peach, guava, lemon, macadamia, coffee and more), a serene pond with goldfish, private hot tub, garden area, and chicken coop. Private, cool-climate setting just minutes to Makawao Town, Seabury Hall, King Kekaulike & Kamehameha Schools, and Makawao Forest Reserve. No HOA. This is a CPR’d property. This home is a MUST-SEE!

34 Alaluana Rd Unit B, Makawao

Listing courtesy of Real Broker.

270 Pau Hana Rd Unit B, Makawao
$1,010,000
2 Beds ⋅ 1 Baths ⋅ 409525 MLS ⋅ Fee Simple Tenure
Step into the charm of 270 Pau Hana Road, nestled in the peaceful heart of Makawao, Maui. This beautifully designed, contemporary 2-bedroom, 1-bathroom home effortlessly combines comfort and style. 744 square feet of inviting living space, (can be expanded to 1,500 sf) with an additional 312 square feet of covered lanai—ideal for soaking up Maui’s breathtaking beauty. Perched on over a half-acre of level, fully useable, CPRd land, this comfortable home offers plenty of room to unwind, entertain, or simply bask in privacy. From the lanai, delight in stunning sunsets, ocean vistas and views of Kahakuloa, while indoors, a thoughtfully crafted interior awaits. The chef’s kitchen is a standout, complemented by sleek, high-tech glass sliding doors that blur the line between indoor and outdoor living. Whether you’re savoring morning coffee with a view or hosting an intimate gathering under the stars, this home is ready to deliver the ultimate island lifestyle. Move-in-ready and brimming with tranquility, this is your chance to embrace Makawao's serene vibe and call this little slice of paradise your own. Don’t wait—your Maui retreat awaits!

270 Pau Hana Rd Unit B, Makawao

Listing courtesy of Compass-W.

7 Hoolai St, Makawao
$999,999
3 Beds ⋅ 2 Baths ⋅ 409706 MLS ⋅ Fee Simple Tenure
Nestled in the heart of charming Makawao town, 7 Hoolai St is a private sanctuary that blends island living with modern comfort. Surrounded by lush, tall hedges and secured with fencing and a gated entry, this 3-bedroom, 2-bath home offers both serenity and convenience. Step inside to discover a freshly painted interior with an inviting open floor plan, abundant natural light, and airy spaces designed for relaxed living. The large windows bring the outdoors in, while the gas range in the kitchen adds a practical yet stylish touch for home chefs. Outside, a spacious open lanai beckons for morning coffee, evening gatherings, or simply soaking in the peaceful surroundings. The beautifully landscaped yard showcases tropical touches, including some of the best banana plants you’ll ever find. This move-in-ready home also offers flexibility—configure part of the layout into a mother-in-law suite with its own living area and kitchenette, perfect for extended family or potential rental income. Need extra storage? The large storage building on the property has you covered. Enjoy the best of Makawao’s vibrant community while retreating to your own private oasis. This property is truly a rare find—don’t let it slip away!

7 Hoolai St, Makawao

Listing courtesy of Compass-W.

1123 Kehau Pl, Makawao
$990,000
3 Beds ⋅ 1 Baths ⋅ 407239 MLS ⋅ Fee Simple Tenure
Welcome to 1123 Kehau Place — a timeless 3-bedroom, 2-bath plantation-style home nestled on a peaceful hillside just above historic Makawao Town. This classic residence with R-3 Zoning offers 1,392 sq ft of living space filled with warmth, character, and sweeping bi-coastal views that stretch to Moloka‘i. Step inside to find gorgeous hardwood floors, custom built-in cabinetry, and inviting wood accents that highlight the home’s old-world charm. The spacious kitchen, updated with slate tile flooring, granite counters, a center island, and crisp white cabinetry, balances plantation character with modern convenience — perfect for gatherings and home-cooked meals. Both bathrooms have been tastefully remodeled, one featuring a tub/shower with hibiscus tile accents, and the other boasting a walk-in shower, double sinks, and space to add your dream clawfoot tub. Set on a generous 11,250 sq ft lot, this property provides room for creativity and expansion — whether you envision a cottage, orchard, or lush tropical gardens. Enjoy morning coffee on the lanai while taking in the magnificent Upcountry breezes and panoramic views. With its quiet surroundings and close proximity to Makawao’s charming shops, galleries, cafes, and schools, this home offers the perfect blend of tranquility and close to town living. Whether you’re seeking a peaceful primary residence or a retreat steeped in Upcountry charm, this Makawao gem is not to be missed.

1123 Kehau Pl, Makawao

Listing courtesy of ENRG Realty.

101 Ulana St Unit B, Makawao
$965,000
2 Beds ⋅ 2 Baths ⋅ 409078 MLS ⋅ Fee Simple Tenure
Welcome to Maui Uplands! This beautiful 2-bedroom, 2-bath home with views of the West Maui mountains was fully renovated in 2023. Luxury vinyl flooring, custom bathrooms, a bright and functional kitchen are just some of the wonderful features of this spacious 1,012 sqft home. Attic insulation was installed to maximize the efficiency of a new Bosch central AC and heating system for those hot summer days and cool upcountry winter mornings. A 200amp power upgrade was completed to the home in April of 2024 along with a Tesla Wall Charger. A privacy fence, brand new hot tub, and concrete slab are the icing on the cake to this sweet upcountry retreat. Maui Upland residents enjoy access to a private, gated pool and tennis courts. Whether you're relaxing indoors or taking in the Mountain views from your lanai, this home is designed to provide a comfortable and enjoyable living experience, making it a perfect place to call home. This is unit B of a CPR Property.

101 Ulana St Unit B, Makawao

Listing courtesy of Pacific Image Properties.

1072 Aala Pl, Makawao
$900,000
2 Beds ⋅ 1 Baths ⋅ 408346 MLS ⋅ Fee Simple Tenure
Welcome to 1072 Aala Place, a charming upcountry property tucked away on a quiet cut-de-sac in the heart of Makawao and experience the perfect blend of comfort, privacy, and the cool Upcountry climate Maui is known for. Inside, you'll enjoy an abundance of natural light streaming through the large picture window overlooking the lush greenery. The open living space flows seamlessly into the kitchen and dining areas, creating an ideal setting for gatherings or relaxed everyday living. Generously sized bedrooms provide comfort and flexibility for family, guests, or a home office. Step outside to your peaceful backyard oasis, surrounded by lush fruit trees and vibrant tropical plants. The property sits on a spacious half acre lot with room for expansion. Located just minutes from Makawao Town's boutiques, cafes, a conveniences, and a short drive to Pukalani, Haiku and premier Upcountry schools, this home is positioned for both lifestyle and convenience. Call your favorite REALTOR to schedule a private showing of this must see property.

1072 Aala Pl, Makawao

Listing courtesy of Real Broker.

245 Mokuahi St Unit Unit A, Makawao
$879,000
2 Beds ⋅ 1 Baths ⋅ 410881 MLS ⋅ Fee Simple Tenure
"Treetops Condominium" is a residential condo sale offerinng the Main dwelling (Unit A) with rights to expand the current footprint and/or build an additional cottage. You'll feel at home in this floor plan that offers comfort and charm. The spacious kitchen with granite countertops, cherrywood cabinets and stainless steel appliances opens to the living room where trees and plants fill every window. Koa laminate flooring connects the living spaces throughout and the generous primary bedroom offers a walk-in closet.The spacious, covered deck adds over 350 sq ft of outdoor entertainment and living space. Underneath the house, you have storage for all your toys, tools and gardening supplies.You’ll love the walkable location to Makawao town with its historical vibe, mixed with boutique shops and dining. From this location, you can be at the airport, shopping, and Baldwin Beach all under 15 minutes. There are no common area maintenance fees. The home is sited on just over 15,000 s.f. of Limited common area yard and serviced by a private cesspool and electric meter. Water usage is shared with the cottage (unit B). Be prepared to submit a pre-approval letter or proof of cash funds with any offer. Listor is Seller and part-owner of the property. Listing Broker/Agent is the Principal and a Sole-Proprietor.

245 Mokuahi St Unit Unit A, Makawao

Listing courtesy of Cheryl L Lee.

How much is your home worth?

Get instant property value now!