Upcountry Homes with Fee Simple Land tenure

Welcome to Upcountry Maui, a hidden gem that beautifully marries the allure of island living with the charm of rural tranquility. Nestled in the heart of Maui, this enchanting region offers breathtaking views of the lush landscapes, rolling hills, and vibrant gardens that make it a sought-after destination for both residents and visitors alike. Known for its cooler climate and stunning vistas, Upcountry is the perfect escape from the hustle and bustle of coastal life, providing a serene backdrop for those seeking a more laid-back lifestyle.

One of the many appealing aspects of Upcountry Maui is its diverse selection of homes, particularly those with Fee Simple land tenure. This means that homeowners enjoy complete ownership of both their property and the land it sits on, giving them the freedom to personalize and invest in their slice of paradise. Whether you’re looking for a charming cottage in Makawao, a sprawling estate in Kula, or a cozy ranch in Olinda, Upcountry offers a variety of properties that cater to different lifestyles and budgets.

In addition to its picturesque homes, Upcountry is rich in cultural experiences, featuring local markets, art galleries, and farm-to-table dining that showcase the best of Hawaiian agriculture. Residents can enjoy hiking trails, breathtaking sunsets, and a strong sense of community, all while being just a short drive from the stunning beaches of the coast. Embrace the unique charm of Upcountry Maui, where every day feels like a vacation and the possibilities for adventure are endless. Come discover your dream home in this idyllic paradise!

Newest Upcountry Homes with Fee Simple Land tenure

$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.

$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..

$4,500,000

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.

$2,700,000

4 Beds ⋅ 3 Baths ⋅ 410633 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).

$1,100,000

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.

$1,569,500

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).

$2,250,000

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.

$1,100,000

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.

$799,000

1 Beds ⋅ 1 Baths ⋅ 410552 MLS ⋅ Fee Simple Tenure

Bring your vision and a contractor to this unique Makawao opportunity. Situated to capture a partial ocean view, this property offers a rare setup featuring a one-bedroom, one-bathroom main residence paired with an attached studio ohana .The bones are solid and offer a fantastic footprint, though they are in need of significant renovation and a complete aesthetic overhaul. This is a true fixer-upper, perfect for a buyer looking to customize a space from the studs up. The potential here is undeniable. Opportunities to secure a view-oriented property with this much upside are few and far between—bring your tools and unlock the possibilities. Property may not conform to County of Maui tax records. Buyer is advised to do their own due diligence

22 Pakani Pl, Makawao

Listing courtesy of Compass-W.

$1,145,000

4 Beds ⋅ 3 Baths ⋅ 410550 MLS ⋅ Fee Simple Tenure

Welcome to 30 Paha‘a Place, a beautifully updated and exceptionally versatile Upcountry Maui home tucked away on a flag lot at the end of a quiet cul-de-sac in Pukalani. Situated on approximately ¼ acre, this private property offers generous indoor and outdoor living, a flexible floor plan, mature landscaping and numerous recent improvements, including nearly 1000 additional square feet of unpermitted bonus rooms with peekaboo ocean views from the backyard and Haleakala views from the front yard. The bright and refreshed main residence features new interior paint and numerous updated doors, fixtures and finishes. The well-appointed kitchen offers cherry cabinetry, granite countertops, stainless steel appliances and gas cooking. Photovoltaic solar panels, solar hot water and seven split-system A/C units add comfort and energy efficiency throughout the property. A converted garage now serves as a spacious bonus room/gym with Murphy bed, offering flexible possibilities for recreation, work or guests. The attached nohana space has also been substantially upgraded with a remodeled kitchen and bathroom, stacked washer/dryer and an enclosed former porch creating additional usable library space. Outside, a newly stained deck and patio overlook the spacious, fully fenced yard shaded by mature fruit trees, with two sheds providing additional storage and garden space. Conveniently located near Pukalani and Makawao shopping, schools, parks and Upcountry amenities, and approximately 15 minutes from Kahului and the North Shore, 30 Paha‘a Place offers the space, flexibility and relaxed lifestyle that make Upcountry Maui living so special. Private. Updated. Versatile. Energy-conscious. And ready for its next chapter.

30 Pahaa Pl, Makawao

Listing courtesy of Keller Williams Realty Maui-Ka.

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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.