Maui Properties

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.

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.

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!

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.

Bring your vision to this peaceful Upcountry property nestled just below the cool cloud line of Upper Piiholo. Set on two (2) beautifully established acres, this three (3) bedroom two (2) bath home offers more than twenty six hundred (2600+) square feet of interior space along with views that create an inspiring backdrop for a thoughtful renovation. Native trees, tall pines, and fragrant eucalyptus surround this property, offering both privacy and a deep connection to the land. The home is ready for someone who appreciates character and craftsmanship and wants to restore it to its original charm. A generous wraparound deck already frames the exterior, inviting a seamless indoor and outdoor lifestyle. Inside, the main level features an open living, dining and kitchen area with vaulted ceilings and a striking stone accented fireplace. Two (2) bedrooms and a full bath completes this floor. The primary suite rests on the upper level, offering treetop views and natural light. The finished basement offers a one (1) car parking garage and a large room, perfect for a home office, home theatre or possibly a work out/yoga studio. With internet available and plenty of room to reimagine both indoor and outdoor spaces, this property is a rare opportunity to create something truly special. Whether you update the existing layout or transform it into a more modern Upcountry retreat, the setting and foundation are already in place. This much loved home is waiting for its next chapter.

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.

Nestled in the heart of charming Makawao, this versatile Maui home offers the perfect blend of space, privacy, and island lifestyle. Situated on a generous 10,000+ sq. ft. lot, the property features a 3-bedroom, 2-bath main residence upstairs filled with natural light and cool upcountry breezes. Downstairs, a 2 bedroom ohana provides flexible living options—ideal for extended family, guests, or potential rental income—while still maintaining a sense of privacy. The expansive lot offers room to garden, entertain, or simply enjoy the peaceful surroundings and open skies that Makawao is known for. Located in one of Maui’s most desirable upcountry communities, you’re just minutes from local schools, shops, restaurants, and the artistic charm of Makawao town, with cooler temperatures and a true neighborhood feel. This property presents a rare opportunity to enjoy multi-generational living or added income potential in a serene, sought-after setting. *A 3D Virtual Tour is available

Thoughtfully reimagined Upcountry residence set on roughly three acres in Maunaolu Plantation, showcasing ocean and mountain views with easy access to the North Shore, Makawao, Paia, and Central Maui conveniences. The interior layout is designed for privacy and balance, with two well-appointed bedroom suites positioned on either side of the central living and kitchen spaces. High-end finishes include Fleetwood doors, Statuary marble countertops, a Lacanche range, Sub-Zero and Fisher & Paykel appliances. Wide decks extend from both sides of the home, creating effortless indoor-outdoor living while capturing morning sun and cooling trade winds; decking is crafted from Thermory Ash, a durable, eco-conscious alternative to Ipe. Additional highlights include ample storage, a detached outbuilding currently used as an office, and a desirable main home building site offering future flexibility.

A rare 5-acre offering along the highly desired upper stretch of Olinda Road, this property delivers the kind of views and setting that define Upcountry living. Positioned beside Haleakala Ranch core lands, the acreage opens toward sweeping bi-coastal vistas, South Shore sunsets, and the rolling pastureland that makes Olinda so treasured. Framed by a striking jacaranda, a towering ficus, and mature landscaping that has evolved over decades, the land carries both history and potential. Multiple vantage points at higher elevations reveal some of the property’s most impressive outlooks—expansive, cinematic, and uniquely private. Improvements on the property include the main house, a secondary rental unit, and a separate art studio. These structures reflect the charm of an earlier era and offer flexible footprints for those looking to update or reimagine the spaces. Many buyers will approach the property with a vision for renovation or new construction to fully maximize the land’s potential. What remains highly valuable is the combination of acreage, established concrete infrastructure, County water service, and a remarkable setting rarely available in this part of Makawao/Olinda.

Welcome to your luxury upcountry home, just a short stroll to Makawao Town but worlds apart. This 4 bedroom, 3 bath house is located at the bottom of a gated driveway inside a master planned development, providing privacy and a "front row seat" on the panoramic, bi-coastal ocean views found there. Upstairs you will find the great room, 3 bedrooms, 2 baths and a spacious, partially covered deck (already roughed in for a hot tub) with elevated north and south shore views. The 4th bedroom and 3rd bath are located on the lower level with a family room and separate entrance, providing a flexible living space that is also perfect for extended family or guests. The spacious 2 car garage has storage alcoves for all the Maui toys, as well as a large workshop area and separate storage room inside. Two outdoor sheds provide additional storage. Other extras include an owned, 24 panel PV solar system on a net meter, a level 2 EV charger, and hard wired surround sound and deck speakers. This home is built to last with lpe decking, hardie board siding, and copper flashings on the exterior, along with bamboo and tiger wood flooring and natural stone interiors. It is sold turn-key, and includes high end custom furnishings. Owner's personal items inside the garage are excluded. This is a Residential CPR. Buyer and Buyer's Agent shall do their own due diligence regarding the use and structures on the property. Owner listed.

Welcome to 1199 Freitas Place in Makawao town — a well-cared-for home that combines functional design with classic island living. This is truly one of the best values in Makawao on a $/sf basis! The property features a 1635 square foot, 3-bed/2-bath main residence and a 667 square foot detached Ohana. Both structures are situated on a lush 0.39 acre corner lot with established fruit trees and versatile outdoor spaces. The main home has been freshly repainted and maintained with great attention to detail. Its thoughtful layout provides a welcoming atmosphere with space for relaxation and entertaining. The separate Ohana, previously used as a hair salon, offers an open floor plan ready to be tailored to your needs — whether as an additional living area, creative workspace, or guest suite. The fenced-in yard showcases a diverse fruit orchard featuring mountain apples, oranges, tangerines, lemons, limes, bananas, peaches, curry leaf, Suriname cherries, ginger and turmeric. Additional structures include a workspace and storage shed, offering flexibility for hobbies or projects, an ocean view deck for relaxing or sunset dinners, and a large generator to keep the home fully powered during outages. The dryer, cooktop and oven are all gas powered. Owners average electric bill has been less than $100/month! Located within walking distance of Makawao Town and Makawao Elementary School, you’ll enjoy the convenience of local shops, dining, and community events, all while feeling tucked away in your own private oasis. This is a property that’s been genuinely cared for, offering a lifestyle that blends nature, creativity, and Maui comfort.

Welcome to true Upcountry Maui living in Makawao Ranch Acres! Tucked away at the end of a quiet cul-de-sac, this charming property features the main home, a detached cottage, and additional space above the garage. The fairly level lot includes both front and back yards, perfect for outdoor entertaining, gardening, and enjoying privacy. Inside, the main house showcases dramatic vaulted ceilings, a fireplace, and an open floor plan. The property is ideally located within walking distance of Historic Downtown Makawao’s galleries, restaurants, The Eddie Tam Memorial Recreation Center, Public Library, schools and a short drive to Kahului Airport, Paia, and Maui’s famed North Shore beaches. This rare Upcountry compound offers flexible living configurations—ideal for multi-generational living, a guest rental, or simply experiencing the Upcountry lifestyle.

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.

This is an amazing and RARE opportunity to own a SINGLE LEVEL home and POOL in Kula 200! Put your own touches and remodeling ideas together for this home with great bones! You'll appreciate the gigantic living room with stone fireplace, a gorgeous open beam ceiling, and views out to the pool! Enjoy the generous den or game room where you and your loved ones or pals can casually relax. In addition to all of this, there is a luxuriously sized primary bedroom opening out to the pool. This is one of the few locations Upcountry that you can truly enjoy a swimming pool! And, you gotta love that outside shower and original pool slide! This 2 acre parcel boasts an elegant Monkey Pod tree, planted by the Owners. The lychee and mango produce beautifully. The location, architecture and price make this an irresistible purchase. Better than that, it could be HOME SWEET HOME.

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.

Welcome to the Meadows at Makawao subdivision. 244 N Makaleha Pl offers a unique opportunity to own a piece of Upcountry Maui. This 1,774 sq ft, 3 bedroom 3 bath single-family home, built in 1988, sits on a generous 9,221 sq ft lot, providing ample space for comfortable living. Enjoy beautiful ocean views from the deck and master bedroom. The Meadows has underground utilities which makes for beautiful unobstructed views of Haleakala. Located on a peaceful cul-de-sac, residents enjoy the benefits of a close-knit community with sidewalks and streetlights, enhancing safety and walkability. The property's location offers convenient access to Makawao Town, upcountry parks, schools, and shopping centers, making daily errands and leisure activities easily accessible. Don't miss this opportunity to make this house a home! Schedule a showing with your favorite realtor today!