Upcountry Homes with Fee Simple Land tenure

Upcountry Homes with Fee Simple Land tenure

Welcome to Upcountry Maui, a hidden gem nestled in the lush hills of Hawaii's enchanting island. This picturesque region, known for its breathtaking landscapes and charming communities, offers a unique blend of serenity and adventure. With its cooler climate and stunning views of both the ocean and the majestic mountains, Upcountry is a paradise for nature lovers and those seeking a peaceful lifestyle.

As you explore this captivating area, you’ll discover a variety of homes that embody the spirit of Upcountry living. One of the most appealing features of these properties is the fee simple land tenure. This means you own both the home and the land it sits on, providing you with the ultimate sense of security and investment potential. Whether you’re looking for a quaint cottage, a sprawling estate, or a cozy farmhouse, Upcountry offers diverse housing options that cater to every taste and lifestyle.

Beyond the homes, Upcountry Maui is rich in culture and community. Farmers' markets brim with fresh produce, local artisans showcase their crafts, and friendly neighbors create a welcoming atmosphere. Enjoy the scenic beauty of the area by hiking through the lush trails of Haleakalā National Park or savoring the stunning sunset views from the slopes of the mountain.

Whether you’re seeking a permanent residence or a vacation retreat, Upcountry Maui promises a lifestyle filled with natural beauty, community spirit, and the freedom that comes with owning your land. Come and experience the charm of Upcountry—your dream home awaits!

Newest Upcountry Homes with Fee Simple Land tenure

136 Ikena Kai Pl Unit Lot G, Kula
$988,000
411225 MLS ⋅ Fee Simple Tenure
Discover an exceptional opportunity to build your dream home in Omaopio Ridge, a beautiful gated community nestled in the rolling hills of Lower Kula, Upcountry Maui. Spanning 5.03 acres, this remarkable parcel offers breathtaking bi-coastal ocean views, spectacular sunsets, and a peaceful setting surrounded by Maui's natural beauty. Perched at approximately 1,400 feet in elevation, the designated building site is in the upper portion of the property, thoughtfully positioned to maximize the stunning panoramic views. Adding tremendous value, award-winning Design Concepts Hawaii has created an impressive custom home design specifically for this property. The purchase price includes conceptual architectural renderings, proposed finish selections, structural and civil engineering plans, and a geotechnical investigation report, providing a valuable foundation for bringing your vision to life. Omaopio Ridge is a thoughtfully planned community featuring an attractive gated entrance, a private water system, and underground utilities, preserving the area's scenic surroundings. Enjoy the refreshing Upcountry climate, expansive open space, and tranquility of country living while remaining approximately 15 minutes from Kahului's shopping, dining, schools, and everyday conveniences. With its generous acreage, captivating views, and extensive architectural planning already completed, this property presents a rare opportunity to create a custom Maui estate in one of Upcountry's most desirable settings. Experience the perfect balance of privacy, natural beauty, and convenience at Omaopio Ridge.

136 Ikena Kai Pl Unit Lot G, Kula

Listing courtesy of Romvari Realty Ltd.

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.

93 Piiholo Rd Unit B, Makawao
$725,000
411068 MLS ⋅ Fee Simple Tenure
This is a Residential Condo Property, Unit B of the Piiholo Meadows Condominium, and is approved for a cottage (farm dwelling of up to 1,500 square feet of living area). Ocean views stretch across Maui’s North Shore to the island of Molokai from these 3.550 acres of open Upcountry pasture on Piiholo Road in Makawao. The property offers convenient access, a manageable footprint, and views of the West Maui Mountains across the isthmus, making it well suited to a farm cottage, a garden-focused homestead, or a peaceful Upcountry retreat. Mornings here are cool and green, and evenings bring sunset light over the ocean and quiet. Makawao town is just minutes away, with galleries, boutiques, cafes, paniolo heritage, the Hui No’eau Visual Arts Center, and the local favorite, Komoda Bakery. Kahului, the airport, and Paia's beaches are an easy drive. Recorded subdivision CC&Rs include protected ocean-view corridors and architectural review, which help preserve the neighborhood’s character and views. There are no monthly HOA dues. The Piiholo area receives consistent Upcountry rainfall, making rainwater catchment a practical and widely used option. Agricultural zoning.

93 Piiholo Rd Unit B, Makawao

Listing courtesy of Compass-W.

93 Piiholo Rd Unit A, Makawao
$1,025,000
411067 MLS ⋅ Fee Simple Tenure
This is a Residential Condo Property, Unit A of the Piiholo Meadows Condominium, and is approved for the main house. Sweeping North Shore ocean views define this 12.007-acre property of rolling Upcountry pasture at the end of a quiet stretch of Piiholo Road in Makawao. From the main home site, the Pacific stretches across Maui’s North Shore to the island of Molokai on the horizon, with the West Maui Mountains across the isthmus. Turn around, and a lush, forested gulch wraps the back of the property, adding green views and natural privacy. A trail leads down from the pasture into scenic Maliko Gulch, whose streambed flows seasonally after Upcountry rains, a memorable walk right from your own land. Up top, roughly six and a half acres of open, usable pasture are ready for a home site, gardens, orchards, or horses. This is Upcountry living at its best: cool mornings, green hillsides, and ocean views that stretch for miles, yet only minutes from Makawao town, with its galleries, boutiques, cafes, the Hui No’eau Visual Arts Center, and the famous cream puffs at Komoda Bakery. Kahului, the airport, and the North Shore beaches of Paia are an easy drive. Recorded subdivision CC&Rs include protected ocean-view corridors and architectural review, which help preserve the neighborhood’s character and views. There are no monthly HOA dues. The Piiholo area receives consistent Upcountry rainfall, making rainwater catchment a practical and widely used option.

93 Piiholo Rd Unit A, Makawao

Listing courtesy of Compass-W.

26 Kula Hwy Unit Unit D, Pukalani
$548,000
411061 MLS ⋅ Fee Simple Tenure
BUILD YOUR MAUI HOME HERE. New Developer Offering! This shy 3/4 acre property is one of two CPR’d Spatial Units currently being offered for sale. Plenty of Room to BUILD YOUR HOME with lots of space for a wonderful yard, garden, open space, or agricultural purposes. Lovely, all Useable, Gently Sloping, approx. 31,799 SF Lot, Makai (oceanside) of the Kula Hwy. above Pukalani. The property is conveniently located to Shopping, Maui's most revered Educational Institutions and the finest UpCountry Maui has to offer. The property offers nice Central Maui, & West Maui Mountain Views with a North Shore corridor view, blending with lots of Sunshine, Fresh Air and just enough Moisture to make this an Ideal Living Climate and Elevation. At night the Stars Abound as do the Twinkling Lights of Central Maui. The Airport and Costco are approx. 15 minutes away, the Hospital 20 minutes, Makawao Town approx. 5 minutes away and not far to Paia, Beaches and World Class Surf. Grasp this wonderful opportunity to own your Piece of UpCountry Maui and begin the Next Chapter of your Life today!

26 Kula Hwy Unit Unit D, Pukalani

Listing courtesy of Maui Real Estate Advisors LLC.

26 Kula Hwy Unit Unit E, Pukalani
$298,000
411062 MLS ⋅ Fee Simple Tenure
BUILD YOUR MAUI HOME HERE. New Developer Offering! This is one of two CPR’d Spatial Units currently being offered for sale. Room to BUILD YOUR OHANA (Accessory Dwelling) with some space for a wonderful small yard, garden, or whatever your heart desires. Lovely, all Useable, Gently Sloping, property Makai (oceanside) of the Kula Hwy. above Pukalani. The property is conveniently located to Shopping, Maui's most revered Educational Institutions and the finest UpCountry Maui has to offer. The property offers potential Central Maui, Kahului Harbor & West Maui Mountain Views blending with lots of Sunshine, plenty of Fresh Air and just enough Moisture to make this what many consider to be an Ideal Living Climate and Elevation. At night the Stars Abound as do the Twinkling Lights of Central Maui. The Airport and Costco are approx. 15 minutes away, the Hospital 20 minutes away, Makawao Town approx. 5 minutes and not far to Paia, Beaches and World Class Surf. Grasp this wonderful opportunity to own your Piece of UpCountry Maui and begin the Next Chapter of your Life today!

26 Kula Hwy Unit Unit E, Pukalani

Listing courtesy of Maui Real Estate Advisors LLC.

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