Upcountry Real Estate

Located in the beautiful state of Hawaii and nestled in the heart of Maui County, Upcountry is a region that offers a unique and enchanting experience. With its picturesque landscapes, cool climate, and rich cultural heritage, Upcountry is a sought-after destination for both residents and visitors alike.

One of the most appealing aspects of Upcountry is its natural beauty. The region is blessed with rolling hills, lush green pastures, and breathtaking views of the Pacific Ocean. It is also home to the majestic Haleakala volcano, which attracts hikers, nature enthusiasts, and stargazers from all over the world. The cool climate of Upcountry makes it an ideal escape from the heat and humidity of the coastal areas, offering a refreshing change of pace.

In addition to its natural wonders, Upcountry is known for its vibrant arts and culture scene. The region is dotted with art galleries, craft shops, and local boutiques, showcasing the talent and creativity of the community. Upcountry also hosts various festivals and events throughout the year, celebrating the island's diverse cultural heritage.

For those seeking a more laid-back lifestyle, Upcountry offers a range of charming towns and communities to choose from. From the historic town of Makawao, known for its cowboy culture and Paniolo (Hawaiian cowboy) traditions, to the quaint village of Kula, famous for its farms and breathtaking views, there is a place for everyone in Upcountry.

Whether you are looking to relocate or simply visit, Upcountry in Maui County, Hawaii, promises a truly unforgettable experience. From its natural beauty to its vibrant arts scene and unique cultural heritage, this region has something for everyone to enjoy.

Newest Listings in Upcountry

$4,400,000

4 Beds ⋅ 3 Baths ⋅ 410494 MLS ⋅ Fee Simple Tenure

This rare Kamaole Kula property is situated on Maui's leeward, sunset coast at an elevation of 2,450 feet. It boasts stunning bi-coastal views and a low-humidity climate with an ideal blend of subtropical days and cool mornings and evenings. Over the years, the original owners have thoughtfully developed and meticulously cared for this beautifully graded and contoured two-acre parcel. Their stewardship has created a mature and thriving landscape featuring approximately 1,000 feet of rock walls, an abundance of productive fruit trees—including avocado, citrus, cherimoya, and macadamia nut—a fertile garden, and exceptional privacy. The sturdy, custom-built home and detached garage were constructed using irreplaceable old-growth, clear vertical-grain (CVG), Western red cedar, sourced from virgin forests in British Columbia. The timber was obtained through a rare special-use permit issued by the Canadian government, allowing the purchase of wind-felled trees approaching 400 years in age that were extracted by helicopter. Even in the 1980s, wood of this caliber was rare; today, it is virtually priceless. This premium lumber is naturally resistant to termites and rot, including all studs and joists, and the home is finished with the highest-grade roof tiles. The construction was executed by master craftsman and boat builder John Cahill, of Cahill Construction. The property also features a 48-panel solar array equipped with top-quality SMA Sunny Boy inverters and a state-of-the-art Heliotex automated cleaning system. Additionally, this parcel benefits from a grandfathered net-zero interactive electric meter with a minimal monthly service charge—a program that has since been discontinued by Hawaiian Electric. Keokea Town is a short drive away, offering convenient access to Ching Store, Fong Store, Grandma's Coffee House, Keokea Park, and the Kula Clinic. Schools and the post office are approximately 10 minutes away. This timeless, classic, one-of-a-kind home is a true real estate outlier. It offers a peaceful and comfortable Maui lifestyle. This is a Residential CPR property. Call your Realtor for a private viewing.

10898 Kula Hwy, Kula

Listing courtesy of Compass-W.

$875,000

2 Beds ⋅ 1 Baths ⋅ 410486 MLS ⋅ Fee Simple Tenure

Discover your own private paradise in this beautifully renovated 2-bedroom, 1-bath cottage nestled in the heart of serene Upcountry Maui. Located at a cool and comfortable 2,200 ft elevation, this charming Kula property offers Haleakala view, open skies, and an ideal year-round cool climate. Surrounded by mature trees and natural beauty, the home features cozy, light-filled living spaces with tasteful upgrades throughout. Enjoy a renovated kitchen, an updated bathroom, and stylish finishes that blend modern tastes with comfort. Fresh interior and exterior paint enhance the bright, airy feel of the home. This CPR unit B can be expanded up to 1500sf. Perfect as a first home or a downsized sanctuary, this move-in-ready cottage invites you to experience the best of Upcountry living.

1298 Naalae Rd, Kula

Listing courtesy of ENRG Realty.

$1,250,000

2 Beds ⋅ 1 Baths ⋅ 410471 MLS ⋅ Fee Simple Tenure

Large sunny easy to build one-half-acre lot with a two-bedroom one bath accessory dwelling. The location of the accessory dwelling towards the rear of the lot provides ample space for your new main dwelling and another accessory dwelling. Amazingly easy to build lot that is flat with multiple building sites to provide privacy and room for your desired home. Accessary dwelling is well maintained to allow living on site or rental income. Reroofed and deck repairs made. On the mauka side of Mikiola with some pine trees in the front, give you that country living feeling. Bearing trees on property include avocado, coconut, lime, and Lemon.

29 Mikiola St, Makawao

Listing courtesy of ZT Hawaii LLC.

$2,000,000

410451 MLS ⋅ Fee Simple Tenure

Take a quick drive down a country road in lower Kula, Maui's breadbasket, and you'll find 20 acres of gorgeous, vacant, gently sloping agricultural land. You will be greeted with big ocean views across the North Shore to Molokai, the West Maui Mountains, and Ma'alaea harbor. When you look mauka, you'll see absolutely majestic Haleakala vistas as well. You may come for the views, but you'll stay for the rich soil and the land's diversity. The most difficult decision you will have to make may be where to build, as there are multiple spots with different perspectives. Gentle access to a gulch along the eastern boundary adds privacy and excellent areas to hike. All at a near perfect altitude in Kula, 2,275 feet of elevation. Aspire to Upcountry living, but want to be close to the airport, shopping, and Maui's finest schools? This property has many options and could serve as a boutique agri-tourism business, horse property, family farm, or private estate. A Maui County water meter is installed near the top of the property. This property was previously used as a nursery and pasture. Call your favorite Realtor for a private tour.

Naele Rd, Kula

Listing courtesy of The Maui Real Estate Team Inc.

$835,000

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.

$1,239,000

3 Beds ⋅ 3 Baths ⋅ 410434 MLS ⋅ Fee Simple Tenure

Set atop a quarter-acre lot across from the 12th fairway in Pukalani Terrace, 185 Hololani Street offers the rare combination of move-in-ready comfort and future potential. The home features 3 bedrooms, 2.5 baths, plus a versatile bonus room ideal as a dedicated office or fourth bedroom, abundant storage, a separate storage room or workshop, and two carports with covered parking for up to three vehicles. A rare private sewer connection enhances the property's long-term flexibility, allowing you to fully enjoy and maximize the land without the constraints of a cesspool or septic system. Whether you envision a future cottage or ADU, expanded living space, or simply the luxury of a generous yard, the possibilities are yours to explore (subject to County approval). Just minutes from Pukalani Country Club, shopping, parks, historic Makawao town, Kulamalu Town Center & food trucks, and some of Maui's most distinguished private schools, this is Upcountry living with room to imagine more.

185 Hololani St, Makawao

Listing courtesy of Coldwell Banker Island Prop(S).

$1,099,000

3 Beds ⋅ 3 Baths ⋅ 410426 MLS ⋅ Fee Simple Tenure

This property is the Main house of a residential CPR. Built in 2021, this beautifully maintained 3-bedroom, 2.5-bath home offers the perfect blend of modern comfort and Upcountry convenience. Ideally situated in Pukalani with easy access to Haleakala Highway. The thoughtfully designed floor plan features bright, open living spaces, contemporary finishes, and a well-appointed kitchen with stainless steel appliances, creating a welcoming atmosphere for everyday living and entertaining. Step outside to a spacious yard with plenty of room for children, furry family members, gardening, or weekend gatherings. Additional highlights include a spacious two-car garage with a dedicated 220-volt outlet, making it ready for electric vehicle charging, along with ample room for storage and outdoor gear. A solar hot water system adds to the home’s energy-efficient features. Conveniently located near some of Upcountry Maui’s highly regarded schools, parks, shopping, dining, and recreational opportunities, this move-in-ready home offers quality construction, modern amenities, and the relaxed Upcountry lifestyle you’ve been searching for.

136 Tam Yau Pl Unit 12H, Makawao

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

$975,000

410418 MLS ⋅ Fee Simple Tenure

Heavenly Kula! This fully fenced property of just over 6 acres is a beautiful pastoral slice of Upcountry life. Located around the 2200' elevation, the climate here is one of the most desirable in all of Maui. A new 5/8" County water meter was recently installed making this the perfect time to get started. Multiple potential homesites with incredible bi-coastal ocean views make this the perfect blank canvas for wonderful Agricultural living. Don't miss this!

Calasa Rd, Kula

Listing courtesy of Compass.

$1,500,000

2 Beds ⋅ 2 Baths ⋅ 410416 MLS ⋅ Fee Simple Tenure

Secluded at the top of Olinda and surrounded by state forest, 115 Alaluana Road offers privacy and profound quiet above Makawao town. Set on 1.4 agricultural acres, this classic Frank Stiller pole home reflects decades of island living through its natural, lived-in character. The two-bedroom, two-bath residence spans 2,113 square feet across two connected, single-level living spaces. Vaulted open-beam ceilings, skylights, and broad windows draw sunlight and greenery indoors, while twin lofts add versatility. The flexible floor plan offers separate great rooms, each with a wood-burning stove, for hosting, working, or creative pursuits. An open-air entry courtyard welcomes you home, while wraparound decks invite outdoor living. The back lanai sets the stage for morning coffee, relaxed meals, sunset gatherings, and stargazing. Beyond the home, an open lawn and a blue-rock retaining wall define the outdoor space, while a 600-square-foot greenhouse with garden beds offers room for growing and hands-on projects. Beneath the main living area, 1,250 covered square feet provide workspace and storage, complemented by an outdoor shower. 115 Alaluana is a unique Upcountry retreat—offering adaptable living spaces, abundant room to work and create, and an intimate connection to nature for those seeking solitude.

115 Alaluana Rd, Makawao

Listing courtesy of Compass-W.

$1,100,000

410399 MLS ⋅ Fee Simple Tenure

One of the most turnkey development opportunities in Upcountry Maui. This 1.8-acre vacant lot comes with its own three rare 5/8" county water meters and county-approved building plans for a main house with an attached ohana ready to break ground. Skip the years of waiting for the county, architectural fees, and uncertainty. Lot A is zoned R-3, which allows for a total of three homes of any size to be built. On level to gently sloping topography, the site offers sweeping views of the North Shore, Haleakala, and the West Maui Mountains. Tucked at the end of a quiet road, you get the peace of a private country setting while still being walking distance to the shops, restaurants, and charm of historic Makawao Town. Baldwin Beach is 10 minutes down the hill, and Costco and the airport are about 20 minutes away. At nearly 1,500 feet elevation, the weather is consistently cool and comfortable. Three water meters. R-3 zoning on nearly two acres. Approved plans in hand. Unit A of a 5.68 acre 3-unit CPR. The hidden gem you've been looking for!

281 Maha Rd Unit Unit A, Makawao

Listing courtesy of Coldwell Banker Island Prop-Ku.

$1,420,000

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).

$1,795,000

5 Beds ⋅ 4 Baths ⋅ 410364 MLS ⋅ Fee Simple Tenure

Tucked away on a quiet cul-de-sac in one of Kula's most sought-after neighborhoods, this beautifully updated 5-bedroom residence combines Upcountry privacy with sweeping ocean and mountain views. Filled with natural light, the main level features an open living area, a renovated kitchen, central air conditioning, and seamless access to the lanai, creating an inviting space for everyday living and entertaining. The lower level offers exceptional flexibility with two bedrooms, two full baths, and a separate sitting area, providing comfortable space for long-term guests, a home office, creative studio, or additional living quarters. Owned photovoltaic solar panels, a garage with durable epoxy flooring and bonus flex space, mature tropical landscaping, and a peaceful setting completes this thoughtfully designed Kula home.

40 Kapalulu Pl, Kula

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

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Based on information from the Multiple Listing Service of Hicentral MLS, Ltd. Listings last updated on . Information is deemed reliable but not guaranteed. Copyright: 2026 by HiCentral MLS, Ltd. IDX information is provided exclusively for consumers' personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.