Upcountry Real Estate

Upcountry Real Estate

Welcome to Upcountry Maui, a hidden gem nestled in the lush hills of Hawaii’s second-largest island. This enchanting region offers a delightful blend of stunning landscapes, rich agricultural heritage, and a vibrant community spirit that captures the essence of island living.

Upcountry is renowned for its cooler climate, which is a refreshing contrast to the tropical warmth found in coastal areas. Here, you’ll find charming towns like Makawao and Kula, each with their own unique character and a warm, welcoming atmosphere. The rolling pastures and panoramic views of the Pacific Ocean create a picturesque backdrop that is simply breathtaking.

Explore the thriving local farms and markets, where you can savor fresh produce, artisanal goods, and the famous Upcountry strawberries. The region is also home to several wineries and distilleries, offering tastings that showcase the unique flavors of the land. For outdoor enthusiasts, the hiking trails in Haleakal? National Park provide exhilarating adventures, leading to stunning vistas and diverse ecosystems.

Cultural experiences abound in Upcountry, from art galleries showcasing local talent to the rich history of the paniolo (Hawaiian cowboy) tradition. Community events, fairs, and festivals foster a sense of belonging, making it easy to connect with neighbors and immerse yourself in the local culture.

Whether you’re looking for a serene retreat, a vibrant community, or a taste of Hawaii’s agricultural heart, Upcountry Maui is a captivating destination that promises to enchant and inspire. Come discover the beauty and charm of this remarkable region, where every day feels like a slice of paradise.

Newest Listings in Upcountry

$1,599,000
4 Beds ⋅ 2 Baths ⋅ 410773 MLS ⋅ Fee Simple Tenure
Over two acres on Makawao Avenue, held by the same owners for generations. The property sits up on a rise in the band between Pukalani and Makawao, with Haleakala above it and open sky in every direction. Cool mornings, usable ground, and a location that needs no explaining to anyone who knows upcountry. The parcel is zoned agricultural and largely open. Room for pasture, orchard, gardens, animals, or equipment, with space left over. A 4 bedroom, 2 bath home sits on the property and is ready to live in now. Makawao town and the shops and restaurants along Baldwin Avenue are minutes away, with Kahului a short drive down the hill. Over two acres fronting Makawao Avenue rarely becomes available, and property held this long tends to sell once and stay put. Come see it in person, since the size and the setting read differently on the ground than they do in photos. Contact your agent to schedule a private showing.

640 Makawao Ave, Makawao

Listing courtesy of Keller Williams Realty Maui-Ka.

$850,000
410767 MLS ⋅ Fee Simple Tenure
Perched along the slopes of Haleakala in serene Upcountry Kula, this rare 3.865-acre agricultural parcel offers an exceptional canvas for your dream island estate, private retreat, or sustainable farming vision. Enjoy sweeping, panoramic bi-coastal ocean views stretching across South Maui to the sparkling Pacific, with stunning vantage points taking in Molokini, Kahoolawe, and Lanai, all framed by dramatic sunsets and gentle mountain breezes. The property features gently rolling pasture terrain with native flora, mature trees, and existing pastoral fencing. At an ideal elevation of approximately 2,250 feet, with crisp mornings and temperate Upcountry weather, this acreage offers total privacy while remaining minutes from Sun Yat Sen Park, Thompson Road, Keokea Park, Grandma's Coffee House, Ulupalakua Ranch, Ulupalakua Vineyards, and Kula's charming community hubs. With convenient direct frontage along Kula Highway and an interior 4WD access pathway already navigated across the land, you have multiple vantage points to envision your custom build. Embrace off-grid sustainability or rainwater catchment in this timeless pastoral setting. Discover the magic of Upcountry Maui living and create a legacy for generations to come.

9900 Kula Hwy, Kula

Listing courtesy of Compass-W.

$1,800,000
410762 MLS ⋅ Fee Simple Tenure
Positioned along the tranquil countryside of Keokea, this exceptional 22.356-acre Upcountry estate parcel presents an unparalleled legacy ownership opportunity on Maui. A tremendous and rare asset is an active, installed 5/8-inch County of Maui water meter, securing vital utility infrastructure in an area where water meters are historically scarce and highly coveted. From sunrise to sunset, command sweeping bi-coastal ocean vistas and dramatic mountain panoramas, taking in the South Maui shoreline, the Central Valley, Molokini Crater, Kaho?olawe, Lana?i, and the West Maui Mountains. Embrace the remarkable versatility of Maui County Agricultural zoning, which allows you to create a premier main home, a second farm dwelling or ohana, equestrian stables, expansive barns, groves, or productive agricultural endeavors. The acreage unfolds across rolling pastureland, mature trees, and peaceful pastoral privacy at an elevation of approximately 2,200 feet, complemented by an internal 4WD pathway that traverses the landscape to multiple prime building sites. Situated just minutes from Grandma's Coffee House, Keokea Park, ?Thompson Road, Sun Yat Sen Park, and Ulupalakua, this magnificent property offers an extraordinary blend of secluded island grandeur, cool elevation breezes, and effortless access to Upcountry living.

275 Kealakapu Rd, Kula

Listing courtesy of Compass-W.

$1,150,000
2 Beds ⋅ 1 Baths ⋅ 410747 MLS ⋅ Fee Simple Tenure
Discover the possibilities with this captivating 2-bedroom, 1-bathroom cottage situated on a little over half an acre of flat, fully usable land. Built in 2013, this well-maintained property was thoughtfully updated in 2022 with a remodeled kitchen and luxury vinyl plank flooring throughout. Enjoy gorgeous ocean views from the patio and beautiful mountain views throughout the property. The cottage features stainless steel appliances, split A/C in the primary bedroom and living room, a solar water heater, and 25 owned photovoltaic panels for added energy efficiency. The expansive lot offers plenty of room to enjoy the outdoors while providing significant future potential. The property also includes a small wood-frame shed for additional storage. The high-capacity septic system was intentionally designed to accommodate the future addition of up to a 5-bedroom home, offering flexibility for expansion along with a concrete tank and leech field. There is ample room to add a main house and potentially another cottage, subject to County approvals, permitting, zoning, and applicable regulations. Recent improvements include new exterior paint, adding to the property's inviting appeal. Whether you're looking for a comfortable cottage, additional space for future development, or a property with room to grow, this unique offering provides an exciting combination of usable land, views, solar infrastructure, and potential. Some photographs have been virtually staged for illustrative purposes.

284 Alalani St, Makawao

Listing courtesy of Shore To Shore Realty, Inc..

$1,659,000
3 Beds ⋅ 2 Baths ⋅ 410729 MLS ⋅ Fee Simple Tenure
Unique on Maui, and nestled in the sought-after Upcountry community of Pukalani, this multi-unit property presents a rare chance to own a plantation style home, inviting cottage, versatile workshop, and two separate flex spaces, all set on over 1/2 acre of fully fenced land. The main residence has just been updated with new interior paint, new vinyl plank flooring, and a revamped kitchen featuring beautiful quartz countertops. It is move-in ready with a bright, clean, fresh feel. Enjoy panoramic views of Haleakala and the West Maui Mountains by day and town lights by night as you unwind in the backyard fire pit area. Two strategically positioned flex space studios offer options for a home office, studio, extra storage, or a small business. The layout ensures privacy with generous spacing between the main house, cottage, and workshop, making it ideal for multi-generational living or rental opportunities. There's also potential for a CPR, offering added flexibility for future development or investment. Situated in one of Maui's most ideal climates, this property is minutes away from multiple schools, community parks, boutique shopping, a local golf course, and variety of favorite dining spots. Truly a must-see opportunity that cannot be fully appreciated from a drive-by. Please schedule a private tour through your realtor today.

190 Aliiolani St, Pukalani

Listing courtesy of Compass-W.

$1,725,000
4 Beds ⋅ 4 Baths ⋅ 410722 MLS ⋅ Fee Simple Tenure
Cool, Calm, and Connected in Kulamanu! Nestled on a large and private corner lot, this well-established 4-bedroom, 3.5-bath home offers a rare combination of space, comfort, flexibility, and beautiful mountain and ocean views. This home has 2,038 square feet of interior living space and is complemented by expansive open and covered decks, large lanai,and covered porch providing for exceptional indoor/outdoor living and entertaining. Enjoy added privacy, a fenced yard, garden space, and established landscaping with producing banana, coffee, and citrus trees.The versatile floor plan features an open kitchen, dining, and living room with wood burning fireplace for those cool Kula nights. Within this floor plan you’ll find two very spacious primary suites, each with its own ensuite bathroom, one on the main floor and one on the lower level making this home exceptionally well suited for multigenerational living, guests, or buyers seeking flexible use of space. The two-car garage provides convenient parking, laundry and additional storage. Located in sought-after Kulamanu, known for its peaceful Upcountry setting, underground utilities, sweeping bi-coastal ocean views, and proximity to schools, farmers’ markets, dining, parks, and quaint Upcountry towns. Some photos have been virtually staged.

8 Paliuli Pl, Kula

Listing courtesy of Kulamanu Realty.

$2,445,000
410713 MLS ⋅ Fee Simple Tenure
There is a freedom that comes with having enough land to think beyond the home itself. Lot 1, encompassing approx. 25 acres, looks out across an extraordinary stretch of Maui, with panoramic Ocean, North Shore, West Maui Mountain, South Shore and Neighbor Island views. Haleakala completes the panorama above the property, giving Lot 1 a sense of openness in nearly every direction. At approximately 2,300 feet elevation, warm Upcountry days transition into cooler evenings in Kula, while gentle trade winds and a temperate climate have long supported both comfortable year-round living and productive agriculture. It is a setting defined as much by how it feels as by what the land makes possible. What distinguishes this parcel is not simply what surrounds it, but the land itself. Unlike many Upcountry properties where acreage can be constrained by steep terrain or limited areas for development, these 25 acres are remarkably usable. The gently contoured landscape creates flexibility for a private estate, agricultural pursuits, guest accommodations, or a combination of uses designed around the land and its surroundings. That flexibility defines Kula I'O, an established, 236 acre, gated agricultural community, with parcels ranging from approximately 2.5 to 25 acres, offering thoughtfully planned view corridors, private infrastructure, and substantial residences already built. A private well system supplies two 60,000-gallon potable water tanks, and a 1.6-million-gallon agricultural reservoir, supporting the community’s agricultural use. Each parcel is served by both potable and agricultural ¾” water meters, with additional County of Maui water service supporting the subdivision’s common areas. With essential infrastructure already established, including underground electric and cable access, ownership begins further along than most vacant land opportunities. The CPR process is also allowed at Kula I’O. The location also places everyday Upcountry conveniences within easy reach. Makawao is just minutes away, along with nearby schools, restaurants, a community center, post office, hardware store, gas station and fire station. Maui Memorial Medical Center, Kahului Airport, Wailuku and Maui’s beaches are also within convenient driving distance, creating a balance between a private Upcountry setting and access to all that Maui has to offer. The Canvass is Exceptional the Rest is Yours.

221 Kalelemuku Pl Unit Lot #1, Kula

Listing courtesy of Maui Real Estate Advisors LLC.

$1,945,000
410711 MLS ⋅ Fee Simple Tenure
There is a freedom that comes with having enough land to think beyond the home itself. Lot 7, encompassing 15+ acres, looks out across an extraordinary stretch of Maui, with panoramic Ocean, North Shore, West Maui Mountain, South Shore and Neighbor Island views. Haleakala completes the panorama above the property, giving Lot 7 a sense of openness in nearly every direction. At approximately 2,250 feet elevation, warm Upcountry days transition into cooler evenings in Kula, while gentle trade winds and a temperate climate have long supported both comfortable year-round living and productive agriculture. It is a setting defined as much by how it feels as by what the land makes possible. What distinguishes this parcel is not simply what surrounds it, but the land itself. Unlike many Upcountry properties where acreage can be constrained by steep terrain or limited areas for development, these 15+ acres are remarkably usable. The gently contoured landscape creates flexibility for a private estate, agricultural pursuits, guest accommodations, or a combination of uses designed around the land and its surroundings. That flexibility defines Kula I'O, an established, 236 acre, gated agricultural community, with parcels ranging from approximately 2.5 to 25 acres, offering thoughtfully planned view corridors, private infrastructure, and substantial residences already built. A private well system supplies two 60,000-gallon potable water tanks, and a 1.6-million-gallon agricultural reservoir, supporting the community’s agricultural use. Each parcel is served by both potable and agricultural ¾” water meters, with additional County of Maui water service supporting the subdivision’s common areas. With essential infrastructure already established, including underground electric and cable access, ownership begins further along than most vacant land opportunities. The location also places everyday Upcountry conveniences within easy reach. Makawao is just minutes away, along with nearby schools, restaurants, a community center, post office, hardware store, gas station and fire station. Maui Memorial Medical Center, Kahului Airport, Wailuku and Maui’s beaches are also within convenient driving distance, creating a balance between a private Upcountry setting and access to all that Maui has to offer. The Canvass is Exceptional the Rest is Yours.

275 Kula I'o Rd Unit Lot #7, Kula

Listing courtesy of Maui Real Estate Advisors LLC.

$1,895,000
410712 MLS ⋅ Fee Simple Tenure
There is a freedom that comes with having enough land to think beyond the home itself. Lot 6 represents the last remaining developer parcel at Kula I'O, encompassing 15+ acres. The property looks out across an extraordinary stretch of Maui, with panoramic Ocean, North Shore, West Maui Mountain, South Shore and Neighbor Island views. Haleakala completes the panorama above the property, giving Lot 6 a sense of openness in nearly every direction. At approximately 2,250 feet elevation, warm Upcountry days transition into cooler evenings in Kula, while gentle trade winds and a temperate climate have long supported both comfortable year-round living and productive agriculture. It is a setting defined as much by how it feels as by what the land makes possible. What distinguishes this parcel is not simply what surrounds it, but the land itself. Unlike many Upcountry properties where acreage can be constrained by steep terrain or limited areas for development, these 15+ acres are remarkably usable. The gently contoured landscape creates flexibility for a private estate, agricultural pursuits, guest accommodations, or a combination of uses designed around the land and its surroundings. That flexibility defines Kula I'O, an established, 236 acre, gated agricultural community, with parcels ranging from approximately 2.5 to 25 acres, offering thoughtfully planned view corridors, private infrastructure, and substantial residences already built. A private well system supplies two 60,000-gallon potable water tanks, and a 1.6-million-gallon agricultural reservoir, supporting the community’s agricultural use. Each parcel is served by both potable and agricultural ¾” water meters, with additional County of Maui water service supporting the subdivision’s common areas. With essential infrastructure already established, including underground electric and cable access, ownership begins further along than most vacant land opportunities. The CPR process is also allowed at Kula I’O. The location also places everyday Upcountry conveniences within easy reach. Makawao is just minutes away, along with nearby schools, restaurants, a community center, post office, hardware store, gas station and fire station. Maui Memorial Medical Center, Kahului Airport, Wailuku and Maui’s beaches are also within convenient driving distance, creating a balance between a private Upcountry setting and access to all that Maui has to offer. The Canvass is Exceptional the Rest is Yours.

257 Kula I'o Rd Unit Lot #6, Kula

Listing courtesy of Maui Real Estate Advisors LLC.

$1,895,000
410709 MLS ⋅ Fee Simple Tenure
There is a freedom that comes with having enough land to think beyond the home itself. Lot 8, encompassing 15+ acres, looks out across an extraordinary stretch of Maui, with panoramic Ocean, North Shore, West Maui Mountain, South Shore and Neighbor Island views. Haleakala completes the panorama above the property, giving Lot 8 a sense of openness in nearly every direction. At approximately 2,200 feet elevation, warm Upcountry days transition into cooler evenings in Kula, while gentle trade winds and a temperate climate have long supported both comfortable year-round living and productive agriculture. It is a setting defined as much by how it feels as by what the land makes possible. What distinguishes this parcel is not simply what surrounds it, but the land itself. Unlike many Upcountry properties where acreage can be constrained by steep terrain or limited areas for development, these 15+ acres are remarkably usable. The gently contoured landscape creates flexibility for a private estate, agricultural pursuits, guest accommodations, or a combination of uses designed around the land and its surroundings. That flexibility defines Kula I?O, an established, 236 acre, gated agricultural community, with parcels ranging from approximately 2.5 to 25 acres, offering thoughtfully planned view corridors, private infrastructure, and substantial residences already built. A private well system supplies two 60,000-gallon potable water tanks, and a 1.6-million-gallon agricultural reservoir, supporting the community’s agricultural use. Each parcel is served by both potable and agricultural ¾” water meters, with additional County of Maui water service supporting the subdivision’s common areas. With essential infrastructure already established, including underground electric and cable access, ownership begins further along than most vacant land opportunities. The location also places everyday Upcountry conveniences within easy reach. Makawao is just minutes away, along with nearby schools, restaurants, a community center, post office, hardware store, gas station and fire station. Maui Memorial Medical Center, Kahului Airport, Wailuku and Maui’s beaches are also within convenient driving distance, creating a balance between a private Upcountry setting and access to all that Maui has to offer. The Canvass is Exceptional, the Rest is Yours.

301 Hoohele Malie Pkwy Unit Lot #8, Kula

Listing courtesy of Maui Real Estate Advisors LLC.

$1,895,000
410707 MLS ⋅ Fee Simple Tenure
There is a freedom that comes with having enough land to think beyond the home itself. Lot 9, encompassing 15+ acres, looks out across an extraordinary stretch of Maui, with panoramic Ocean, North Shore, West Maui Mountain, South Shore and Neighbor Island views. Haleakala completes the panorama above the property, giving Lot 9 a sense of openness in nearly every direction. At approximately 2,200 feet elevation, warm Upcountry days transition into cooler evenings in Kula, while gentle trade winds and a temperate climate have long supported both comfortable year-round living and productive agriculture. It is a setting defined as much by how it feels as by what the land makes possible. What distinguishes this parcel is not simply what surrounds it, but the land itself. Unlike many Upcountry properties where acreage can be constrained by steep terrain or limited areas for development, these 15+ acres are remarkably usable. The gently contoured landscape creates flexibility for a private estate, agricultural pursuits, guest accommodations, or a combination of uses designed around the land and its surroundings. That flexibility defines Kula I'O, an established, 236 acre, gated agricultural community, with parcels ranging from approximately 2.5 to 25 acres, offering thoughtfully planned view corridors, private infrastructure, and substantial residences already built. A private well system supplies two 60,000-gallon potable water tanks, and a 1.6-million-gallon agricultural reservoir, supporting the community’s agricultural use. Each parcel is served by both potable and agricultural ¾” water meters, with additional County of Maui water service supporting the subdivision’s common areas. With essential infrastructure already established, including underground electric and cable access, ownership begins further along than most vacant land opportunities. The location also places everyday Upcountry conveniences within easy reach. Makawao is just minutes away, along with nearby schools, restaurants, a community center, post office, hardware store, gas station and fire station. Maui Memorial Medical Center, Kahului Airport, Wailuku and Maui’s beaches are also within convenient driving distance, creating a balance between a private Upcountry setting and access to all that Maui has to offer. The Canvass is Exceptional the Rest is Yours.

328 Hoohele Malie Pkwy Unit Lot #9, Kula

Listing courtesy of Maui Real Estate Advisors LLC.

$1,295,000
3 Beds ⋅ 2 Baths ⋅ 410649 MLS ⋅ Fee Simple Tenure
Set on a spacious 0.5-acre lot in beautiful Kula, this charming two-story home offers 3 bedrooms, 2 bathrooms, and approximately 2,032 square feet of living space. Fresh exterior paint and a new roof, both completed in 2026, provide a fresh and well-maintained exterior. Enjoy wonderful ocean views from the bedrooms, along with the added efficiency of a solar water heater. A two-vehicle garage provides convenient covered parking and additional storage. The expansive property is beautifully complemented by mature landscaping, including multiple varieties of fruitful avocado trees and citrus trees throughout the grounds. A beautiful poinsettia bush welcomes you in the front yard and becomes especially spectacular during the Christmas season, when it is in full bloom and adds a festive burst of color to the property. With its generous lot, ocean views, mature fruit trees, and desirable Kula setting, this home offers a wonderful opportunity to enjoy the peaceful beauty and unique character of Upcountry Maui. Some photos have been virtually staged.

70 Akea Pl, Kula

Listing courtesy of Shore To Shore Realty, Inc..

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