Upcountry Homes for Sale

Upcountry Homes for Sale

Welcome to Upcountry Maui, a hidden gem nestled in the heart of Hawaii. This enchanting region is renowned for its lush landscapes, cool climate, and breathtaking views of both the Pacific Ocean and the majestic Haleakal? volcano. Here, you’ll find a harmonious blend of rural charm and modern conveniences, making it an ideal place for those seeking a tranquil lifestyle while remaining close to the vibrant energy of Maui's coastal towns.

As you explore Upcountry, you’ll be captivated by its diverse agricultural heritage, with rolling pastures, thriving farms, and colorful flower fields dotting the landscape. The area is home to charming towns like Makawao, known for its rich paniolo (cowboy) culture, and Kula, where you can enjoy stunning sunsets and panoramic vistas. With an array of local markets, art galleries, and outdoor adventures, Upcountry Maui offers a unique lifestyle that celebrates both nature and community.

For those considering a move to this idyllic region, there are a variety of homes for sale that cater to different tastes and budgets. From quaint cottages and spacious ranch-style homes to luxurious estates with sprawling gardens, Upcountry has something for everyone. Whether you’re looking for a peaceful retreat or a family home with room to grow, you’ll find properties that perfectly embody the spirit of island living.

Embrace the opportunity to call Upcountry Maui home, where the beauty of nature meets the warmth of community. Discover your dream home today and start your journey in this captivating paradise!

Newest Upcountry Homes for Sale

85 Ulana St, Makawao
$1,700,000
5 Beds ⋅ 3 Baths ⋅ 411184 MLS ⋅ Fee Simple Tenure
Welcome to 85 Ulana Street, a versatile Upcountry property located in the desirable Maui Uplands neighborhood of Makawao. Situated in a peaceful residential setting, the property features a spacious 5-bedroom, 3-bath main residence along with a detached 2-bedroom, 1-bath cottage, offering excellent flexibility for extended family, guests, a home office, or rental income. Mature landscaping and the generous outdoor space create a private Upcountry atmosphere with room to enjoy Maui’s year-round indoor-outdoor lifestyle. Maui Uplands is conveniently located between Makawao and Pukalani, providing easy access to schools, shopping, restaurants, and everyday conveniences while maintaining the quiet residential feel Upcountry is known for. Community amenities include a swimming pool, tennis court, and clubhouse. With a main residence and detached cottage, 85 Ulana Street presents a unique opportunity for those looking for additional living space, rental potential, or a flexible multi-generational property in one of Makawao’s established neighborhoods.

85 Ulana St, Makawao

Listing courtesy of Commercial Prop of Maui LLC.

3260 Kihapai Pl, Makawao
$1,449,000
3 Beds ⋅ 3 Baths ⋅ 411172 MLS ⋅ Fee Simple Tenure
This is it! A super convenient location, a house and ohana, heated swimming pool and best of all… The seller is offering a 4.25% Assumable VA loan…and yes, non-veterans are eligible. This property has been well cared for and is ready for a buyer that wants a turnkey move-in experience. With a 2 to 3 minute drive to Pukalani Terrace and Pukalani Superette, and approximately a 15 minute drive to Kahului makes this property ideally located. The main house features many upgrades including, but not limited to, a 19-panel PV system with Enphase battery back-up, a full kitchen remodel, new flooring throughout, new window coverings, the interior walls are newly plastered, a tub to shower conversion in the main bath, and a beautifully retiled pool with heating system installed in 2026. The back deck overlooks the heated pool and is perfect for outdoor entertaining and year around swimming. The backyard is fully fenced for privacy and security. The 2nd home features a 19 panel PV system, solar water, newer appliances, new kitchen counter and large pantry, and easy access to a spacious back yard, with a covered lanai and gazebo for outdoor gatherings.

3260 Kihapai Pl, Makawao

Listing courtesy of Welcome Hawaii Properties.

734 Upper Kimo Dr, Kula
$975,000
2 Beds ⋅ 1 Baths ⋅ 411123 MLS ⋅ Fee Simple Tenure
Welcome to 734 Upper Kimo Drive, where breathtaking bi-coastal views, Upcountry charm, and numerous possibilities come together in one extraordinary setting. Perched along the slopes of Haleakala, this special property captures sweeping views of Maui’s North and South Shores, offering a spectacular panorama stretching from the mountains to the Pacific Ocean. Steeped in the rich agricultural heritage of Upcountry Maui, this remarkable location celebrates a lifestyle defined by open spaces, rolling green pastures, and a deep connection to the land. Enjoy warm summer days, cooler winter nights, refreshing mountain breezes, and the peaceful rhythm of country living. The property features an approximately 900-square-foot, two-bedroom ohana, along with an elevated building site offering an exceptional opportunity to envision and create your dream home while taking full advantage of the epic views. Whether you’re looking to establish an Upcountry retreat, embrace Maui’s agricultural lifestyle, or create a legacy property for generations to come, 734 Lower Kimo Drive offers a rare opportunity to turn that vision into reality. This is more than just a property. It’s an opportunity to experience the very best of Upcountry Maui, where spectacular scenery, agricultural heritage, and an extraordinary lifestyle come together.

734 Upper Kimo Dr, Kula

Listing courtesy of Coldwell Banker Island Prop(S).

462 Ainakula Rd, Kula
$4,500,000
3 Beds ⋅ 4 Baths ⋅ 411120 MLS ⋅ Fee Simple Tenure
Views Galore. Kula Orchards Coffee Farm Estate is Maui’s gem, a true estate on the slopes of Haleakala at 3200ft elevation with a sweeping wide unobstructed bicoastal view, just 25 minutes to town. Set behind gates on 2.77 fully fenced acres, this one-of-a-kind estate unfolds around a custom three-bedroom, three-and-a-half-bath residence with three car garage. An expansive open-beam great room creates the heart of the home, complemented by white oak floors, custom cherry cabinetry, and new appliances in the kitchen and laundry room. Other features include solar panels with Tesla battery, reverse osmosis water filter, resort style decks and a large multipurpose or game room. The home is tastefully furnished with custom Kimo’s furniture and has 2 separate entertainment systems with surround sound. Winding paths lead from the residence into established orchards where coffee grows alongside cacao, avocado, citrus, peach, apricot, apple, pear, papaya, banana, pineapple, guava, olive, tropical flowers, and other carefully cultivated plantings. A greenhouse and 12-zone smart irrigation system support the agricultural landscape while a new custom flex building offers additional space for agricultural pursuits. A bonus new improvement to the property is a separate 5/8-inch water meter offering an option to build an additional residence or expand the orchards.

462 Ainakula Rd, Kula

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

122 Ka Dr, Kula
$1,875,000
3 Beds ⋅ 3 Baths ⋅ 411090 MLS ⋅ Fee Simple Tenure
Expansive ocean and island views take center stage from this spacious 3-bedroom, 2.5-bath, 3,034 sq. ft. home near the top of popular Kula Kai. The open main level is filled with natural light, with large windows framing the impressive views and sliding doors opening to a covered deck—an ideal extension of the living space and a wonderful place to enjoy the Upcountry setting. The main residence also features PV panels and an attached 2-car garage. Set on over one-third of an acre, the property includes a detached 1-bedroom cottage with its own driveway and carport, providing excellent flexibility for guests, extended living, a home office or potential rental use. Located in long-established Kula Kai, this property offers generous living space, versatility and truly remarkable views. All furniture and furnishings are either staged or virtually staged.

122 Ka Dr, Kula

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

50 Kaalele Pl, Kula
$2,700,000
4 Beds ⋅ 3 Baths ⋅ 411081 MLS ⋅ Fee Simple Tenure
At the top of Kula’s sought-after Kulamanu neighborhood sits Kaalele Place: where the sunlight reflects off the manicured hedgerows, framing some of the best views on the island. As you approach the very top of the neighborhood, 50 Kaalele Place comes into view. With striking Hawaiian-style architecture, its presence will make you proud to call it home. Unobstructed five-island views from the entire main floor (including the luxurious primary suite), impeccable high-end finishes, a curb appeal rarely found in Upcountry: this is the house that asks you to compromise absolutely nothing. Long-term guests and family will appreciate the private lower level, with its own expansive living areas, 1-car garage, as well as a spacious full bath and bright guest bedroom with walls of windows. The star of the show, however, is the main level. After entering through the automatic gate clad with exotic hardwood, pull into your oversized 2-car garage, and enter your home, only to be greeted by views that will take your breath away, day or night. This level boasts tall wood-accented ceilings, a primary suite you will never want to leave, a stunning two-sided fireplace, a chef’s kitchen with a SubZero refrigerator and Wolf gas range, two additional bedrooms, an additional full bath, and a lanai framed by high-end zero-maintenance aluminum Knotwood railing and pillars. With whole-house water filtration, a top-of-the line solar + Tesla battery system that all-but eliminates your grid reliance, and the ability to live exclusively on one level if desired, this house thought of everything - so you don’t have to. No to-do lists, no compromises, no worries - 50 Kaalele Place is a home you can take the time to enjoy.

50 Kaalele Pl, Kula

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

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.

41 Poha Pl, Pukalani
$2,700,000
4 Beds ⋅ 3 Baths ⋅ 411027 MLS ⋅ Fee Simple Tenure
1973 was the year Secretariat ran the fastest Triple Crown in history, American troops came home from Vietnam, and lines at gas stations wrapped around the block. But in Kula 200, someone poured a masonry foundation on a fresh two-acre lot and built a home meant to last. When a stretch of Upcountry agricultural land was divided into two hundred two-acre parcels, it gave rise to what is known today as Kula 200, one of the most sought-after pockets along the edge of Kula and Pukalani/Makawao. Built in 1973, with a distinctive brick and masonry exterior, generously proportioned rooms, vaulted tongue-and-groove ceilings, and a wood-burning fireplace anchoring the sunken living room. Two bedrooms are en-suite, and a library/den and an extra room off primary suite create additional flexibility. Storage is abundant throughout. The setting may be the property's greatest asset. Positioned at the end of a cul-de-sac with no through traffic, the home sits privately within two fully fenced acres with a new lawn, zoned irrigation, mature landscaping, and views stretching across the valley to the West Maui Mountains, ocean, and Haleakala. Much of the interior remains original, and that's part of the opportunity. Rather than paying for someone else's renovation choices, the next owner can approach the home as a blank canvas and create an interior specific to their own taste. An enclosed sunroom and lanai take advantage of the views and Upcountry setting, while an owned photovoltaic system adds a practical update to this 1973 home. Currently tenant-occupied through May 2027, there is time to plan thoughtfully for what comes next. Two private acres, enduring craftsmanship, expansive views, and a Kula 200 location ready for its next chapter.

41 Poha Pl, Pukalani

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

1160 Ehu Rd, Makawao
$1,500,000
3 Beds ⋅ 2 Baths ⋅ 411002 MLS ⋅ Fee Simple Tenure
Enjoy the space, privacy and cooler climate of Upcountry living in this single-level 3-bedroom, 2-bath home set on 2.5 level, usable acres. High vaulted ceilings create an open, airy feel, while a wrap-around covered deck extends the living space outdoors and provides a comfortable setting to enjoy the peaceful surroundings. The fully fenced and gated property features an expansive green lawn with plenty of room to enjoy the acreage. A detached 2.5-car garage offers space for two vehicles plus a workshop, storage or hobby area. Privately situated yet easy to show, this Upcountry property combines comfortable single-level living with generous usable land and versatile outdoor space. Photos have been virtually staged. This is not a CPR. Zoning allows for 1 main house, a 2nd dwelling of up to 1,500 sf. (permitting conditions apply).

1160 Ehu Rd, Makawao

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

143 Leiohu Cir, Makawao
$2,641,000
3 Beds ⋅ 3 Baths ⋅ 410991 MLS ⋅ Fee Simple Tenure
Enjoy cool upcountry breezes, bicoastal views and the convenience of nearby Makawao Town in this thoughtfully upgraded ranch style residence. Situated in a gated community on a peaceful cul-de-sac, this home showcases quality upgrades and timeless finishes throughout including; cherry wood cabinetry, soft close drawers, gas cooktop, double ovens, new dishwasher and quartz countertops blending warmth and functionality. The home includes a gas fireplace, gas tankless water heater, 15 PV panels (leased, transferable to qualified buyer) and a Tesla charger delivering modern performance with island practicality. The outdoor space is equally inviting with established grapefruit, lemon and avocado trees. A beautiful home being offered furnished (with a separate bill of sale) , bring your personal touch and make 143 Lei‘ohu Circle your Maui Dream Home.

143 Leiohu Cir, Makawao

Listing courtesy of Keller Williams Realty Maui-Ki.

1175 Kamehameiki Rd, Kula
$1,200,000
3 Beds ⋅ 2 Baths ⋅ 410974 MLS ⋅ Fee Simple Tenure
Coming soon. Currently tenant occupied.

1175 Kamehameiki Rd, Kula

Listing courtesy of Coldwell Banker Island Prop(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.

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