Upcountry Homes for Sale

Upcountry Homes for Sale

Welcome to Upcountry Maui, a hidden gem nestled in the lush, rolling hills of Hawaii’s second-largest island. This enchanting region offers a unique blend of serene landscapes, charming small towns, and a vibrant agricultural community, making it an ideal destination for those seeking a tranquil lifestyle away from the hustle and bustle of coastal living.

Upcountry is renowned for its breathtaking views, with panoramic vistas of the Pacific Ocean and the majestic Haleakalā volcano. The climate here is pleasantly mild, providing the perfect environment for growing an array of fruits, flowers, and vegetables. Residents enjoy a slower pace of life, with opportunities for outdoor activities like hiking, horseback riding, and exploring local farmers' markets filled with fresh, organic produce.

When it comes to homes for sale in Upcountry, the options are as diverse as the landscape itself. From charming plantation-style cottages to sprawling estates with acres of land, there’s something to suit every taste and lifestyle. Many properties boast expansive gardens, stunning views, and the tranquility that comes with rural living. Whether you’re looking for a cozy retreat or a family home with room to grow, Upcountry Maui has a variety of listings that cater to your needs.

Experience the magic of Upcountry Maui, where the spirit of aloha thrives in every corner. Discover your dream home in this idyllic paradise, and embrace a lifestyle that celebrates nature, community, and the beauty of island living. Your slice of paradise awaits!

Newest Upcountry Homes for Sale

4 Beds ⋅ 3 Baths ⋅ 410811 MLS ⋅ Fee Simple Tenure

Makawao charm, privacy, and versatility, all within walking distance of town. Located on Piikea Place, a quiet cul-de-sac, this remodeled and well-maintained property features a 4-bedroom, 2.5 bath main home, plus a legal, attached 600 sf ohana with its own entrance, kitchenette, and bathroom. The main home's open-plan kitchen and living area make it easy to prepare meals while remaining part of the conversation. The kitchen features a gas stove and bar counter for casual dining and gathering. A 400+ sf enclosed lanai with vaulted, open-beam ceilings provides additional flexible living space. The home also includes a dedicated laundry area, gas dryer, and solar water heater. The versatile layout offers several possibilities: live in the main home and rent the ohana, accommodate extended family or guests, or use the entire property for rental income. Outside, lush landscaping creates a sense of privacy and tranquility. The fully fenced backyard features two raised garden beds, a gazebo, surfboard racks, and two storage sheds. Five on-site parking spaces, plus ample street parking, make coming and going easy for residents and guests. The property is currently tenant-occupied. Please do not disturb the tenants. Showings are available by appointment only.

3650 Piikea Pl, Makawao

Listing courtesy of Compass-W.

1 Baths ⋅ 410809 MLS ⋅ Fee Simple Tenure

First time to market, an incredible corner lot with a charming 500 sq ft cottage, situated in a prime Lower Kula location within Kula Lani Estates. Enjoy the tranquility, convenience, and breathtaking Upcountry beauty with easy access to everything Kula has to offer. This rare gem presents an extraordinary opportunity to expand on a spacious 21.824 sq ft Rural Zoned lot. The property already features a graded building site with two separate entrances if desired. The well-built, fully equipped cottage includes a full kitchen, bathroom, and cozy sleeping area-allowing you to live comfortably on-site while you build your dream estate. A golden opportunity awaits here on the corner of Lower Kula H and Akea Pl.

11 Akea Pl, Kula

Listing courtesy of Coldwell Banker Island Prop(P).

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.

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..

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.

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.

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..

5 Beds ⋅ 5 Baths ⋅ 410637 MLS ⋅ Fee Simple Tenure

Recently completed, brand New custom 5,000 sq ft home with a 3 car garage in the magnificent Kula I'o neighborhood. Perched at the top of a hill, lot 29 a 2.5 acre parcel gently slopes and enjoys morning sun, mountain, and ocean views. A large infinty edge lap pool with spa, baja ledges, and fountain bubblers overlook a picturesque sunset ocean horizon. This masterfully designed home provides a 4 bed 4 bath main residence with a versatile guest wing that could be used for ohana, gym, or a game room.

173 Huahua Pl, Kula

Listing courtesy of Big Wave Realty LLC.

3 Beds ⋅ 2 Baths ⋅ 410627 MLS ⋅ Fee Simple Tenure

Welcome home to 742 Kekona Place, tucked into the heart of Makawao. If you love the charm of country living, the sense of community that comes with a small town, & the convenience of being approximately 20 minutes from the beach, this Upcountry home offers a wonderful blend of it all. Thoughtfully maintained and beautifully updated, 742 Kekona Place is a home where the attention to detail is immediately apparent. The kitchen was refreshed in 2026 with quartz countertops, high-end cabinetry, new lighting fixtures, & a bespoke backsplash inspired by the colors & movement of the sea. Automatic blinds add another thoughtful touch, bringing both convenience and a clean, modern feel to the home. The 500+ sqft garage has been transformed into the ultimate hangout space, creating an incredible extension of the home & an easy connection between indoor and outdoor living. Whether used as a game room, home gym, workshop, entertaining space, or the ultimate "mancave," it adds flexibility and plenty of room to spread out. Outside is where this property truly comes to life. Tropical landscaping, hot tub, ambient lighting, & multiple seating areas create a private backyard oasis that feels especially magical in the evenings. The front lanai wraps around the side of the home, offering even more space to relax outdoors, while a high-end fence accented with beautiful lighting adds privacy & a polished, resort-like feel. The location is equally special. Enjoy fast access to Makawao town with new sidewalks being built, as well as nearby Eddie Tam Park where a new playground is also being added. The Makawao Rodeo grounds are closeby too, putting some of Upcountry’s best-loved community spots right at your fingertips. Every corner of 742 Kekona Place has been thoughtfully enhanced with an eye toward comfort, function, & the smallest details. Come experience this special home for yourself & feel the magic of Makawao.

742 Kekona Pl, Makawao

Listing courtesy of Coldwell Banker Island Prop-Ku.

3 Beds ⋅ 3 Baths ⋅ 410602 MLS ⋅ Fee Simple Tenure

Tucked privately at the top of a cul-de-sac, this beautifully appointed 3-bedroom, 3-bath home plus office is a Makawao residence that offers a rare combination of thoughtful design, lush surroundings, private pool, intimate outdoor spaces, and an exceptionally flexible floor plan. The home feels both gracious and wonderfully easy to live in, with a sense of privacy and tranquillity that is increasingly difficult to find. Upstairs, an inviting living room is warmed by a cozy gas fireplace, while expansive windows draw in abundant natural light and frame the verdant surroundings. The kitchen and living spaces open naturally toward the home's vine-draped lanai on the lee side- the Owner's favorite place to gather, dine, and enjoy the sweet views toward Makawao sunsets. The spacious primary suite offers a private retreat, complete with built-in bookshelves and a serene sense of separation from the rest of the home. Downstairs feels like its own private world. Two additional bedrooms and an exceptionally generous second living room create a versatile configuration for guests, extended family, a home office, or live-in relatives. From the bedrooms, step directly onto your private lanai and toward the pool and gardens, creating an effortless connection to the outdoors. Outside, the beautifully landscaped grounds are designed for privacy and enjoyment. A fabulous intimate lap pool and cozy pool pavilion provides a peaceful focal point for this residence. For energy efficiency, the property is also equipped with 32 photovoltaic panels. The location is equally compelling. Enjoy the charm of Makawao town within walking distance, while Kahului and Baldwin Beach are approximately 20 minutes away. Here, thoughtful architecture, lush grounds, privacy, flexible living spaces, and an enviable Upcountry setting come together in a truly special property. A distinctive home with wonderful possibilities.

1102 Mailuna Pl, Makawao

Listing courtesy of Equity One Real Estate Inc (P).

3 Beds ⋅ 1 Baths ⋅ 410586 MLS ⋅ Fee Simple Tenure

Discover the exceptional opportunity to own over 21 acres of agricultural land in beautiful Kula, Maui. Offering expansive ocean and mountain views across Central Maui. Approximately 7 acres are usable farmland, providing a versatile setting for farming, agriculture pursuits, or a private Maui estate. The property features a charming 3-bedroom, 1-bath plantation-style home, along with a workshop and multiple work bays - ideal for agricultural operations, equipment storage, hobbies, or additional workspace. The productive farm area is securely fenced to help keep axis deer out and protect crops. With two water meters, substantial acreage, useable farmland, existing improvements, and breathtaking views, this property offers rare combination of functionality, privacy, and Upcountry Maui beauty. A unique opportunity to create your own agricultural retreat while enjoying the cool climate and scenic character that makes Kula so special.

302 Naalae Rd, Kula

Listing courtesy of Yoshida Realty Group.

2 Beds ⋅ 3 Baths ⋅ 410570 MLS ⋅ Fee Simple Tenure

Perched in Upcountry Maui with sweeping ocean views, this custom Pukalani residence is a rare blend of craftsmanship and comfort. The home is Unit C of a very friendly Residential CPR. Imperial plaster walls run throughout, lending a warm, hand-finished texture you won't find in a typical build, while thoughtful custom touches elevate every room. Enjoy a spacious covered lanai, a two-car garage, and generous bonus space in the large finished loft. Upstairs, the main living level features two bedrooms and two bathrooms.The kitchen features quartzite countertops, glass-front cabinetry, and bar seating. Vaulted ceilings in the kitchen and living room create a bright and airy environment. Downstairs, a flex space with separate entrance and half bath offer a great opportunity for guests. Contact your favorite Realtor to schedule a showing.

84 Loha St Unit Unit C, Pukalani

Listing courtesy of Keller Williams Realty Maui-Ka.

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