Upcountry Homes with Detached Ohana

Upcountry Homes with Detached Ohana

Welcome to Upcountry Maui, a hidden gem nestled in the heart of Hawaii that beautifully marries breathtaking landscapes with a serene lifestyle. This enchanting region, perched at a higher elevation, boasts stunning views of the Pacific Ocean, lush greenery, and the majestic Haleakal? volcano. Known for its cooler climate and rich agricultural heritage, Upcountry is a haven for those seeking a peaceful retreat while still being close to the vibrant culture of Maui.

One of the most appealing aspects of Upcountry living is the availability of homes with detached ohanas. These charming, self-contained units provide the perfect opportunity for multi-generational living, guest accommodations, or even a rental income source. Imagine having your own private space just steps away from your main home, where family and friends can enjoy their own slice of paradise. With the flexibility that detached ohanas offer, homeowners can create a personalized living arrangement that suits their unique needs.

The Upcountry area is renowned for its local farmers' markets, artisanal shops, and exquisite dining options, all of which reflect the rich cultural tapestry of Hawaii. Residents enjoy a close-knit community, where neighbors become friends, and the spirit of ‘Aloha’ thrives. Whether you’re exploring the picturesque landscapes of Kula, the charming town of Makawao, or the lush pastures of Pukalani, Upcountry Maui offers an idyllic lifestyle that’s hard to resist.

Experience the best of island living in Upcountry Maui, where homes with detached ohanas await to welcome you to your next chapter in paradise!

Newest Upcountry Homes with Detached Ohana

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.

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).

1199 Freitas Pl Pl, Makawao
$1,200,000
3 Beds ⋅ 2 Baths ⋅ 410916 MLS ⋅ Fee Simple Tenure
Up country living at its best downtown Makawao. Lightfilled 3 bed, 2 bath one story home, new vinyl windows throughout. Expansive living room that moves into a large entertainment room, & an additional room that leads to the covered patio. Enjoy the large fenced lot filled with an abundance of fruit trees, established hedge for privacy, & roomy tool shed. The main bath has been beautifully remodeled with custom tile, counter top, & storage. Kitchen boasts new countertops & tile backsplash. The original kitchen sink stainless steel with side boards, not to be missed. Huge 2 car garage with storage, laundry room & bath with furo. Detached cottage is approx. 660 st. ft with its own electric meter and carport. A blank canvas for you to make it your own. Easy to show. This location is close to the Makawao rest., shops, entertainment, famous Komoda Bakery, schools, gyms, and other amenities.

1199 Freitas Pl Pl, Makawao

Listing courtesy of Chris Bakeman Realty LLC.

140 Kahala Pl, Kula
$2,495,000
2 Beds ⋅ 1 Baths ⋅ 410870 MLS ⋅ Fee Simple Tenure
3 1/2 acres of fertile farm ground with 1 1/2" water meter and bonus buildings. Seller may Carry Owner Financing with large down and fair terms. (2) 2 Bedroom 1 bath homes plus an addition 4480 sq ft bonus building with septic, electric and plumbing that can be used as farm operations building or you can apply for permit to make it the main house. 710 Sq ft Ohana has it's own cesspool and there is also another bonus stand alone octagonal office or yoga studio. 888 sq ft Main house also has a bonus office/ohana next to it and it's own cesspool. This property is a must see. Close to Makawao town and Pukalani. Only 20 minutes to north shore beaches and Paia. Perfect for Owner Farmer who needs housing for workers or Contractor who needs equipment storage and worker housing. Multiple Mango, Avocado, Lychee, Coconut and other mature fruit bearing trees. Dead end Street for safety and privacy. Seller may consider seller financing with acceptable terms.

140 Kahala Pl, Kula

Listing courtesy of Pacific Shores Realty.

190 Aliiolani St, Pukalani
$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.

68 Ka Dr, Kula
$2,235,000
3 Beds ⋅ 3 Baths ⋅ 410282 MLS ⋅ Fee Simple Tenure
Enjoy the best of Upcountry Maui from this beautifully maintained Kula Kai residence offering spectacular bi-coastal ocean views, comfortable single-level living, and exceptional flexibility. The thoughtfully designed 3 bedroom, 3 bathroom main home offers 2,340 sq. ft. of living space and is complemented by a private detached 680 sq. ft. 1 bedroom cottage, ideal for extended family, guests, or additional living space. Recent improvements include a new roof and fresh interior and exterior paint. The open-concept floor plan is highlighted by vaulted wood ceilings, a gas fireplace in the living room, abundant natural light, and an updated kitchen complete with a large quartz island, premium appliances, dual ovens, and a walk-in pantry. A loft above the main living area provides the perfect space for a home office or quiet retreat with sweeping island views. The spacious primary suite includes dual walk-in closets, a spa-inspired bath, and an adjoining bonus room ideal for an office, fitness room, or library. Outdoor living is a true highlight, with multiple lanais, an outdoor kitchen, and landscaped grounds featuring mature fruit trees and terraced gardens. Stargaze from the private hot tub and rinse off after a day in the garden in the outdoor shower. Additional amenities include split-system air conditioning, whole-house water filtration, on-demand hot water, separate utility services for the main home and cottage, photovoltaic infrastructure in place (panels not reinstalled following the new roof), an oversized attached two-car garage with loft storage, a second two-car garage beneath the cottage, and a versatile detached studio perfect for creative or recreational use. Located in one of Kula's most desirable neighborhoods at approximately 2,500 feet elevation, this exceptional property offers the ideal combination of privacy, panoramic views, and the cool Upcountry climate, all within easy reach of schools, shopping, dining, and Central Maui.

68 Ka Dr, Kula

Listing courtesy of Compass-W.

1740 Piiholo Rd, Makawao
$2,649,000
5 Beds ⋅ 4 Baths ⋅ 410159 MLS ⋅ Fee Simple Tenure
Crest the rolling hills and you’ll discover this breathtaking Upcountry Maui estate: a one-of-a-kind property with a rare combination of privacy, expansive space, and timeless charm. The property lies on 4.38 acres of vibrant, open land. It could be your own little oasis, with lush landscaping and tranquility within a short driving distance to charming Makawao Town. The main residence is custom-built with rich redwood walls on both the interior and exterior, a dramatic fireplace hearth formed from black lava rock, teak bannisters, and other handcrafted architectural details throughout. The brand-new deck stretches around the home, providing glorious views of both the mountains and the North Shore. This home was built with love, and the living experience is sure to be warm and absolutely unforgettable. Beyond the primary residence, this property boasts a separate cottage with its own private entrance. This second dwelling offers exceptional flexibility for guests, extended family, or even rental potential.

1740 Piiholo Rd, Makawao

Listing courtesy of Coldwell Banker Island Prop(S).

15 Olinda Rd, Makawao
$2,350,000
5 Beds ⋅ 4 Baths ⋅ 409724 MLS ⋅ Fee Simple Tenure
Also listed under Multi-Dwelling (MLS 409725). This unique multi-unit property (4 structures, 8 units) offers a rare opportunity for investors seeking strong cash flow and long-term upside. There are 5 one bedroom units, and 3 two bedroom units. Situated on just over half an acre, the property features four separate structures with a total of eight tenant-occupied units, creating an income-producing compound in one of Upcountry Maui’s most desirable locations. Tenants enjoy dedicated parking, on-site laundry, and the convenience of being moments from Makawao’s shops, restaurants, galleries, and local charm. Numerous improvements have already been completed, making this an attractive opportunity for an investor looking to step into an established rental property with immediate income potential. The property also has 3 water meters. Listing includes photos of one of the 8 units. A truly one-of-a-kind upcountry investment property.

15 Olinda Rd, Makawao

Listing courtesy of eXp Realty.

191 Alohilani St, Makawao
$1,249,000
2 Beds ⋅ 2 Baths ⋅ 410052 MLS ⋅ Fee Simple Tenure
House and cottage! Now offering a $20,000 buyer credit at closing. The main home has two-bedrooms, with a bonus room that could be used as a third bedroom. The cottage has two bedrooms and one half bathroom. The well-cared-for main home includes a covered, screened lanai with ocean and mountain views and an owned solar system to keep electric bills down. A covered hot tub is a great place to watch the sunset and melt away the day’s cares. Plenty of storage is available, including a large closet off the carport and a separate shed for all your yard tools or Maui toys. The cute, cozy cottage has its own lanai with views of Haleakala, the West Maui Mountains, and the ocean. The well-landscaped property offers a mix of beautiful flowers, edibles, and native plants. Handsome stone terraces at the front of the property are interspersed with lime, sugar cane, pohole fern, starfruit, ohia, papaya, banana, and a variety of herbs. The property’s convenient location is within walking distance of Pukalani Park, the Upcountry Pool, and Pukalani Terrace Shopping Center. It is a short drive to Central Maui or North Shore Beaches. It's a tidy, move-in-ready package for Upcountry Home buyers. Contact your favorite Maui Realtor to set up a showing today.

191 Alohilani St, Makawao

Listing courtesy of The Maui Real Estate Team Inc.

162 Koheo Rd, Kula
$1,650,000
3 Beds ⋅ 2 Baths ⋅ 409893 MLS ⋅ Fee Simple Tenure
Tucked just off coveted Polipoli Road in Kula, this remarkable Upcountry estate is a rare blend of artistic legacy, architectural pedigree, and timeless Maui beauty. Once home to celebrated Hawai‘i artist and educator Richard “Dick” L. Nelson — creator of the renowned Tri-Hue watercolor technique the property reflects a life inspired by creativity, tranquility, and the extraordinary natural surroundings of Upcountry Maui. Designed in collaboration with distinguished mid-century architect Edward Sullam, a protégé of legendary architect Vladimir Ossipoff and architect of the original Shops at Wailea, the residence was thoughtfully positioned to embrace breathtaking bi-coastal views stretching from mountain to ocean. A charming one-bedroom cottage welcomes you near the entry, while the main residence sits gracefully atop the property, capturing panoramic vistas, golden sunsets, and the peaceful ambiance that makes Kula one of Maui’s most treasured communities. The home showcases quality construction and timeless architectural design with expansive windows, skylights, and abundant natural light throughout. Rich character and warmth are felt in every space. One of the three bedrooms served as Dick Nelson’s private art studio and features its own separate entrance, creating endless possibilities for a creative retreat, guest suite, family room, home office, or private sanctuary. The spacious primary suite offers two walk-in closets and easy access to a beautifully appointed bath with dual vanities, walk-in shower, and heated towel bar. The additional bedroom is ideal for guests, or flexible work-from-home living. The kitchen features koa-accented cabinetry, updated built-in appliances, and stainless-steel refrigeration, blending island character with everyday functionality. The open plan living/dining/kitchen features a wood burning fireplace, vaulted wood ceiling, built in credenza and a front viewing deck perfect for drinks at sunset. A two-car garage with loft storage adds convenience and practicality. Located in the heart of Kula, this exceptional property offers the coveted Upcountry lifestyle — cool evenings, scenic paths, and close proximity to beloved local destinations including Grandma’s Coffee House, Kula Bistro, the Kula Market, Haleakala Waldorf School, and Kula Elementary. Nearby attractions such as the Lavender Farm, Strawberry Farm, and Ulupalakua Ranch & Winery complete the idyllic Maui experience. Rarely does a property combine such artistic provenance, architectural significance, and awe-inspiring beauty. This is more than a home, it is a legacy property where inspiration, serenity, and Maui’s finest views come together in perfect harmony.

162 Koheo Rd, Kula

Listing courtesy of ENRG Realty.

2450 Piiholo Rd, Makawao
$4,750,000
3 Beds ⋅ 4 Baths ⋅ 409873 MLS ⋅ Fee Simple Tenure
This 10 acre Piiholo property at 4,000' elevation borders a 41-acre State forest and has incredible ocean and mountain views. The very distinctive and extraordinary main residence, designed by renowned architect Jim Hestand of Maui Architectural Group, is an absolute work-of-art. Almost entirely constructed with old-growth redwood, the architectural inspiration was designed for the well-known concerts and poetry gatherings among the owners in the days of its grandeur...a true legacy property. The main home has recently been thoroughly and lovingly returned to its original beauty and beyond, with the remodeling and modernizing of the kitchen and bathrooms. All of the out-buildings, concrete driveway and landscaping have also been restored. Rare peace and privacy are assured within the grounds. The 2nd residence is reminiscent of a mountain cabin vibe. The 2 residences are separated by many usable acres of trees and orchards. One could certainly imagine this property being ideal for horses. In between the two homes there is an artist/musician studio with flexible use. There are 2 water meters, serving each end of the property. Additionally, there is a large garage/workshop and a useful farm structure. Pi'iholo, is known for cool days and cooler evenings with passing mists, reliable rainfall and refreshing trade winds. There are several respected public schools and excellent private schools in the region. Farmers markets, supermarkets and roadside stands assure you can keep your shopping Up Country. The range of restaurants is remarkable. And for health care, Up Country has it all.

2450 Piiholo Rd, Makawao

Listing courtesy of Coldwell Banker Island Prop(P).

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