Maui Properties

This 10 acre Piiholo property at 4,000' elevation borders a 41-acre State forest and has incredible ocean and mountain views. The very distinctive and extraordinary main residence, designed by renowned architect Jim Hestand of Maui Architectural Group, is an absolute work-of-art. Almost entirely constructed with old-growth redwood, the architectural inspiration was designed for the well-known concerts and poetry gatherings among the owners in the days of its grandeur...a true legacy property. The main home has recently been thoroughly and lovingly returned to its original beauty and beyond, with the remodeling and modernizing of the kitchen and bathrooms. All of the out-buildings, concrete driveway and landscaping have also been restored. Rare peace and privacy are assured within the grounds. The 2nd residence is reminiscent of a mountain cabin vibe. The 2 residences are separated by many usable acres of trees and orchards. One could certainly imagine this property being ideal for horses. In between the two homes there is an artist/musician studio with flexible use. There are 2 water meters, serving each end of the property. Additionally, there is a large garage/workshop and a useful farm structure. Pi'iholo, is known for cool days and cooler evenings with passing mists, reliable rainfall and refreshing trade winds. There are several respected public schools and excellent private schools in the region. Farmers markets, supermarkets and roadside stands assure you can keep your shopping Up Country. The range of restaurants is remarkable. And for health care, Up Country has it all.

Spacious, private, and full of character, 25 Lumahai Place, just off Olinda Road, sits on 2.88 acres with sweeping ocean and West Maui mountain views, cool fresh air, and temperatures that feel like spring year round. A 2,732 square foot main home and detached cottage, 5-7 minutes from Seabury Hall and Makawao Town. The main home's soaring wood-beam ceilings and wood-burning fireplace set a warm, welcoming tone from the moment you walk in. The living and dining areas flow naturally to a the lanai where the views take center stage. The kitchen is generous in size, flooded with natural light, and thoughtfully appointed with granite and butcher block countertops, a farmhouse sink, walk-in pantry, and a picture window perfectly framing the landscape outside. New refrigerator and stove were added in 2026, along with an updated under-sink water filtration system. A solar PV system with battery storage keeps energy costs in check. The primary suite is privately situated with vaulted ceilings, a gas stove, and a beautifully updated ensuite featuring dual vanities, walk-in shower, and soaking tub. Fresh paint and a fully redone second bathroom reflect the care and attention put into this home. Two additional bedrooms, a dedicated laundry room, built-in storage, and a finished loft, ideal as a library, playroom, or fun creative space, complete the main level. Downstairs, a separate 1-bedroom, 1-bath space with its own entrance and newly added sliding door offers excellent flexibility for guests, extended family, or a home office. The recently remodeled detached cottage has its own driveway, parking area, and cement stairs, providing true separation and privacy, and built to last. Perfect for multigenerational living, long-term guests, or rental income. Extensive eucalyptus clearing has opened up the property, improving views, natural light, and usable space while preserving its peaceful Upcountry character. Wake to birds singing and fall asleep to the sound of wind moving through the trees.

Perched in coveted Upcountry Maui, this original Plantation-style 3-bedroom home captures breathtaking north and south shore views, sweeping across the entire Central Valley to the majestic West Maui Mountains. Large picture windows in the living room take in the huge view as does the kitchen window. A full bath adjoins the bedrooms while a half bath completes the laundry room. An enclosed patio opens up with patio doors to the living room and the large 2 car garage and work area. Rich with timeless charm and character, this property offers an incredible opportunity to restore and create one of the area's most desirable residences. Set up high on a spacious lot, the property features a magnificent mature monkeypod tree, expansive outdoor space, and endless potential for indoor-outdoor island living. With R-3 zoning, there is also the added possibility of constructing an additional dwelling, making this an exceptional investment or multigenerational opportunity. Bring your vision and transform this special property into a true Upcountry gem — where stunning views, classic Hawaiian charm, and future potential come together in one remarkable setting.

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!

Some properties are simply beautiful. Others leave you feeling something long after you’ve gone. Perched along the breathtaking slopes of Olinda Road on over 2 private acres, this extraordinary Upcountry estate is the kind of place people spend years hoping to find on Maui. Expansive yet deeply inviting, refined yet grounded, it offers a rare sense of peace and awe the moment you arrive. Towering skies, sweeping bi-coastal views, cool Olinda air, and the feeling of being completely surrounded by Maui’s natural beauty make this property truly unforgettable. Designed for gathering, celebrating, resting, and living fully, the estate offers a stunning 5,000+ sq ft main residence, attached apartment, detached cottage, and expansive barn/workspace creating an incredibly rare opportunity for multigenerational living, deep community, creativity, and connection. At the center of the home, the kitchen naturally draws people together with its breathtaking Spalted Mango island, custom cabinetry, artistic concrete countertops, and walls of windows framing Maui’s North and South Shores. It is easy to picture slow mornings with coffee as the clouds roll over Haleakala, long meals shared around the table, and evenings where conversations continue long after sunset. Outside, the grounds feel abundant and alive. Mature avocado trees produce some of the best avocados you will ever taste alongside thriving banana and citrus trees woven throughout the property. The infinity-edge pool, spa, pickleball court, basketball court, expansive lawns, and countless outdoor gathering spaces create an environment where family and friends naturally want to linger. Inside, every space has been thoughtfully designed to feel both grand and welcoming. Multiple living areas, a sunroom with a fireplace, spacious bedrooms, and beautifully curated finishes throughout create a home that lives as comfortably as it entertains. Whether hosting intimate dinners, large celebrations, retreats, weddings, or simply enjoying a quiet evening under the stars, the property adapts effortlessly to every season of life. What makes this estate truly special is not simply its size, amenities, or breathtaking views. It is the feeling of possibility that exists here. It is a place where generations can gather, where children can run freely, where creativity can flourish, and where some of life's most meaningful moments naturally unfold. Rarely does a property combine luxury, privacy, functionality, and soul in such a remarkable way. 1630 Olinda Road is more than a home. It is a legacy property, an Upcountry sanctuary, and a once-in-a-lifetime opportunity to own one of Maui's truly exceptional estates.

Discover a rare opportunity to own approximately 11.3 acres in the peaceful Hali’imaile/Makawao area. This private agricultural-zoned Lot A CPR parcel offers ocean and mountain views, cool breezes, and a true Upcountry ranch feel. Located within the Kaluanui Ridge 7-lot subdivision, the property is conveniently positioned between Makawao and Paia, with approximately a 5-minute drive in either direction. At an elevation of about 1200 ft this area reportedly gets an average of about 59 inches of rainfall per year and mostly sunny days all year round. This spacious property offers the privacy, open space, and quiet rural lifestyle that make Upcountry Maui so desirable. The land is mostly fenced and includes an approx. one-acre fenced animal pasture, making it well suited for livestock, farming, homesteading, or creating your ideal Maui country retreat. The lot also borders a drainage reserve, providing additional privacy and a natural buffer. Two existing container home dwellings are already in place. The larger dwelling features 4 bedrooms, a kitchen, bathroom, 40ft storage container, off-grid solar system with 21 PV panels, inverter setup, and roughly 14 kWh of 48V battery storage, and an 800-gallon water catchment system. The second container dwelling includes 2 bedrooms, 1 bathroom, kitchen, and catchment system, with power available by generator or from the main solar setup. Enjoy privacy, acreage, views, and the peaceful beauty of Maui’s Upcountry lifestyle—all while remaining close to town, beaches, schools, shops, and conveniences.

This 3 bedroom, 1 bathroom home offers approximately 1,132 square feet of interior living space and is situated on a spacious 8,730 square foot lot. Ready for renovation, this property presents an excellent opportunity for buyers looking to customize, improve, or invest in an Upcountry Maui property with potential. Conveniently located near Haliimaile General Store and a nearby community park, the property enjoys a desirable location with easy access to local dining, outdoor recreation, and everyday conveniences. Bring your vision and creativity to restore and transform this property into something truly special.

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!

If home is where your horse is, try imagining yourself on this 9.618-acre ranch in the heart of Maui's cowboy town, Makawao! With a 16-stall horse barn and a climate-controlled tack room, a huge riding arena used for horse shows, training, and riding lessons, and farm buildings filling every corner, this has been a working ranch for the last 25 years. The primary dwelling was originally built as a barn but was converted into a 4-bedroom, 3-bath, 2,914 sq. ft. amazing home with windows looking out on the ranch as well as barn-high ceilings that give a spacious feeling to the heart of the house! Enjoy extreme comfort with cooling and heating mini-splits in every room! Wind down the rustic center spiral staircase to the mother-in-law style lower-level, where you'll find 2 of the bedrooms and the laundry room. Across from the main arena is the original home that is now a completely rebuilt cottage with a large attached studio... a great place for a ranch manager to live. The possibilities are endless with this versatile property!

265 Ohaoha Place offers the kind of Upcountry Maui lifestyle so many dream about. This spacious, single-level estate property is located in the gated community of Maunaolu Plantation Estates, ideally situated between historic Makawao Town and lively Paia Town. Set on 2 flat, usable, and beautifully manicured acres, the property is complimented by many mature fruit trees, creating a peaceful and inviting setting with ample room to enjoy wide-open space and island living. The approximately 2,456 sq ft main home features 4 bedrooms, 2 full baths, and 2 half baths, while the approximately 1,006 cottage built in 2021, offers 2 bedrooms, 2 full baths, and an expansive covered patio that serves as a true highlight for relaxed outdoor living. Both dwellings feature new roofs and owned PV solar, adding efficiency and long- term value. Rich with original charm, the property presents a wonderful opportunity for a new owner to make it their own. With nearby access to some of Maui’s most sought-after schools, beautiful Haleakala views, and endless space to dream and grow, 265 Ohaoha Place is a rare Upcountry offering.

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.

Beautiful, ocean view Kama’aina estate ideally located in Lower Olinda…just ¼ mile to Seabury Hall. Completely remodeled, charming and elegant plantation-style home built in the 1939 has all the character of times gone by with the refined touches of today’s thoughtful upgrades. Wrap-around covered lanai overlooks the pool, spa, views and natural beauty of the grounds. Entry lanai opens to spacious living room with fir floors and fireplace. Bright & open kitchen and dining area are also positioned to enjoy the ocean and sunset views and also opens up to covered lanai. Upper level also features three bedrooms and one bath—including beautiful primary bedroom with private lanai. Completely remodeled downstairs works as an ideal guest quarters and features nice bedroom area, disappearing privacy doors, large bathroom, kitchenette and open living area with fireplace…from which you may step right out to pool area and spa. Enjoy the fruit and ambiance of having many mature trees. Nicely landscaped grounds feature design by Chris Curtis with automated sprinklers, large amazing fruit trees, irrigation and dramatic night lighting. Tasteful circular driveway welcomes you from the gated entry off of Olinda Road. Workshop/studio space with toilet/sink and outdoor shower off of garage. Solar hot water, Photo voltic grid-tie plus battery system and gas fireplaces. Abundant built in storage, book-cases and drawers. Mature & fruit trees include: mango, avocado, acai berry, lemon, lime, kukui, coffee, lychee, grapefruit, surnam cherry, tangerine, longuan, magnolia, coral & monkeypod. Completely fenced.

New Opportunity awaits in Makawao! Experience the best of Upcountry living in this maintained single-level home tucked away on a quiet cul-de-sac in one of Makawao’s most desirable neighborhoods. This move-in ready gem features vaulted ceilings, abundant natural light, refreshing cross breezes, owned photovoltaic panels, solar hot water, wood flooring, and a spacious two-car garage. Enjoy indoor-outdoor living with a generous backyard perfect for relaxing or entertaining, all while being just minutes from charming Makawao Town, Eddie Tam Park, schools, shopping, restaurants, and only 15 minutes to beaches and Kahului’s major amenities. Don’t miss this incredible opportunity to enjoy the perfect blend of Upcountry charm, comfort, and island convenience—Schedule your private showing today!

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.

Looking to build Upcountry? 11 Huliamahi Place offers a compelling combination of location, views, and usability. This B unit of a two-unit CPR offers an acre of gently sloped land, views of the ocean, Haleakala, and the West Maui Mountains, and entitlements to build a cottage of up to 1,500 square feet. There is plenty of space to build your home, grow a garden, and plant an orchard. Private water and underground utilities run to the land. There is a storage container for you to keep gardening tools, and building supplies before you build. The location is hard to beat for convenience and climate. It is just minutes away from Kulamalu. There you will find the Saturday Upcountry Farmer’s market, food trucks, Longs Drugs, Farm to Table food at Marlow, organic produce at Okoa Farms Store, and libations at the Lahaina Brewing Company. Other Upcountry restaurants, shops, and amenities are close by in Pukalani and Makawao Town. Central Maui and North Shore Beaches are just 15 minutes away. If you are interested in building your home and life Upcountry, contact your favorite Realtor to arrange a showing.

Your whole family will have space in this energy efficient, turnkey, Bungalow Style, multi-level "Mini Mansion" It's nestled Upcountry on Haleakala. Walking distance to schools and Historical Makawao Town and short drive to town, beaches, and airport. 3 bedroom 2 baths can be divided into a separate 1 bd 1 ba attached ohana with private yard, kitchen, driveway, and entrance that easily could be rented. A new perimeter fence has created 5 enclosed unique yards. Living on a private road is safe for kids and pets. Extra large, tall carport with a workshop and observation deck on top with an incredible view creates one of the best spaces on the property. Pictures don't do it justice I'm able to email more detailed pictures I look forward to hearing from you. All comments, data is provided by seller or seller's representatives. Buyer to confirm all & hold all parties harmless from any discrepancy data in the mls and advertising. Limited Service–Data Entry Addendum signed by seller/s must be signed by buyer/s with Purchase Contract.

Enjoy space, flexibility, and privacy in this charming 3-bedroom, 2-bath home situated on 2 beautiful, useable, acres (not a CPR). Tucked away at the end of a cul-de-sac and bordered by a gulch, the setting feels peaceful and secluded. Inside, adaptable living areas easily accommodate a growing household, remote work, hobbies, or guests. The covered deck gives the feeling of indoor/ outdoor living and is a great place to entertain…..or curl up with a good book. Neat, clean and well-cared for, this home is move-in ready. And did I mention: it’s being sold furnished! Just bring your personal touches and enjoy.

Welcome to 3584 Baldwin Avenue in the heart of Makawao—where Upcountry charm meets thoughtful design and everyday comfort. This beautifully finished single-level 3-bedroom, 2-bath home offers an ideal blend of modern upgrades and classic country character, just steps from the shops and restaurants of Makawao Town. Inside, warm acacia engineered hardwood flooring flows seamlessly throughout, creating a cohesive and inviting feel. The kitchen is both stylish and functional, featuring stainless steel appliances, polished concrete countertops, hardwood cabinetry, and an oversized farmhouse sink—perfect for gathering, cooking, and entertaining. An efficient heat pump AC system, along with ceiling fans, ensures year-round comfort in Makawao’s sought-after climate. Step outside to enjoy the home’s welcoming oversized wraparound front deck, ideal for morning coffee, sunset conversations, or just taking in the Upcountry ambiance. Cedar shingle siding adds timeless appeal and enhances the home’s classic plantation aesthetic. A versatile bonus room with its own covered deck offers flexible space for a home office, studio, guest overflow, or creative retreat. This is an exceptional opportunity to own a move-in-ready home in one of Upcountry Maui’s most desirable and walkable towns. Some photos virtually staged.

Upcountry Maui living at its finest. Approximately 2,500 sq ft under roof featuring a 960 sq ft main upper level with 1 bed / 1 bath and an open-concept layout. Remodeled kitchen and bath (Spring 2022) with new granite and marble countertops, island with bar seating, built-in window seat, wood-burning fireplace with tile surround for cozy nights, and a designated interior laundry area for easy access. Enjoy 704 sq ft of lanai space — now partially covered — allowing year-round indoor/outdoor living in Makawao’s cool climate. The lower level offers over 1,500 sq ft of finished space with a separate entrance, 4 rooms with tall ceilings and a bath. Conforming as shop/storage, providing flexibility for hobbies, workspace, or creative use. There are also additional perks you’ll only discover in person. This beautifully well-maintained exterior is surrounded by lush, mature landscaping including olive, avocado, liliko'i, guava, peach, tropical flowers, and more. Relax in the backyard oasis featuring a serene pond home to goldfish and a private hot tub — your own Upcountry retreat. Private and peaceful with close proximity to Makawao Town, Seabury Hall, King Kekaulike & Kamehameha Schools, and convenient access to Makawao Forest Reserve. No HOA dues. Cool climate. A world-away feel with everyday convenience. This is a CPR'd property.

Discover a rare investment opportunity just steps away from the charming town of Makawao! This diverse property features 3 livable structures. A main house built in 1964, two separate cottages constructed in 1942, all currently tenant-occupied. In addition, there is a spacious Quonset hut. The Quonset hut presents versatility, suitable for a workshop, art studio, music studio, or additional storage. The homes are set amongst a lush, mature landscape with avocado trees, a variety of thriving citrus and bananas. A tropical ambiance and plenty of potential for fruitful harvests. This unique property layout is ideal for anyone seeking rental income, or multi-generational living arrangement. With existing tenants in place. Don't miss this unique opportunity to own a piece of paradise close to Makawao, where rural charm meets modern convenience!