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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.

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.

$1,449,000

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.

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.

$1,200,000

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.

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.

$2,649,000

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.

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).

$2,350,000

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.

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.

$1,249,000

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.

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.

$4,750,000

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.

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).

$1,999,000

Spacious, private, and full of character, 25 Lumahai Place, just off Olinda Road, sits on 2.88 acres with sweeping ocean and West Maui mountain views, cool fresh air, and temperatures that feel like spring year round. A 2,732 square foot main home and detached cottage, 5-7 minutes from Seabury Hall and Makawao Town. The main home's soaring wood-beam ceilings and wood-burning fireplace set a warm, welcoming tone from the moment you walk in. The living and dining areas flow naturally to a the lanai where the views take center stage. The kitchen is generous in size, flooded with natural light, and thoughtfully appointed with granite and butcher block countertops, a farmhouse sink, walk-in pantry, and a picture window perfectly framing the landscape outside. New refrigerator and stove were added in 2026, along with an updated under-sink water filtration system. A solar PV system with battery storage keeps energy costs in check. The primary suite is privately situated with vaulted ceilings, a gas stove, and a beautifully updated ensuite featuring dual vanities, walk-in shower, and soaking tub. Fresh paint and a fully redone second bathroom reflect the care and attention put into this home. Two additional bedrooms, a dedicated laundry room, built-in storage, and a finished loft, ideal as a library, playroom, or fun creative space, complete the main level. Downstairs, a separate 1-bedroom, 1-bath space with its own entrance and newly added sliding door offers excellent flexibility for guests, extended family, or a home office. The recently remodeled detached cottage has its own driveway, parking area, and cement stairs, providing true separation and privacy, and built to last. Perfect for multigenerational living, long-term guests, or rental income. Extensive eucalyptus clearing has opened up the property, improving views, natural light, and usable space while preserving its peaceful Upcountry character. Wake to birds singing and fall asleep to the sound of wind moving through the trees.

4 Beds ⋅ 3 Baths ⋅ 409809 MLS ⋅ Fee Simple Tenure

Spacious, private, and full of character, 25 Lumahai Place, just off Olinda Road, sits on 2.88 acres with sweeping ocean and West Maui mountain views, cool fresh air, and temperatures that feel like spring year round. A 2,732 square foot main home and detached cottage, 5-7 minutes from Seabury Hall and Makawao Town. The main home's soaring wood-beam ceilings and wood-burning fireplace set a warm, welcoming tone from the moment you walk in. The living and dining areas flow naturally to a the lanai where the views take center stage. The kitchen is generous in size, flooded with natural light, and thoughtfully appointed with granite and butcher block countertops, a farmhouse sink, walk-in pantry, and a picture window perfectly framing the landscape outside. New refrigerator and stove were added in 2026, along with an updated under-sink water filtration system. A solar PV system with battery storage keeps energy costs in check. The primary suite is privately situated with vaulted ceilings, a gas stove, and a beautifully updated ensuite featuring dual vanities, walk-in shower, and soaking tub. Fresh paint and a fully redone second bathroom reflect the care and attention put into this home. Two additional bedrooms, a dedicated laundry room, built-in storage, and a finished loft, ideal as a library, playroom, or fun creative space, complete the main level. Downstairs, a separate 1-bedroom, 1-bath space with its own entrance and newly added sliding door offers excellent flexibility for guests, extended family, or a home office. The recently remodeled detached cottage has its own driveway, parking area, and cement stairs, providing true separation and privacy, and built to last. Perfect for multigenerational living, long-term guests, or rental income. Extensive eucalyptus clearing has opened up the property, improving views, natural light, and usable space while preserving its peaceful Upcountry character. Wake to birds singing and fall asleep to the sound of wind moving through the trees.

25 Lumahai Pl, Makawao

Listing courtesy of Compass-W.

$3,400,000

If home is where your horse is, try imagining yourself on this 9.618-acre ranch in the heart of Maui's cowboy town, Makawao! With a 16-stall horse barn and a climate-controlled tack room, a huge riding arena used for horse shows, training, and riding lessons, and farm buildings filling every corner, this has been a working ranch for the last 25 years. The primary dwelling was originally built as a barn but was converted into a 4-bedroom, 3-bath, 2,914 sq. ft. amazing home with windows looking out on the ranch as well as barn-high ceilings that give a spacious feeling to the heart of the house! Enjoy extreme comfort with cooling and heating mini-splits in every room! Wind down the rustic center spiral staircase to the mother-in-law style lower-level, where you'll find 2 of the bedrooms and the laundry room. Across from the main arena is the original home that is now a completely rebuilt cottage with a large attached studio... a great place for a ranch manager to live. The possibilities are endless with this versatile property!

4 Beds ⋅ 3 Baths ⋅ 409325 MLS ⋅ Fee Simple Tenure

If home is where your horse is, try imagining yourself on this 9.618-acre ranch in the heart of Maui's cowboy town, Makawao! With a 16-stall horse barn and a climate-controlled tack room, a huge riding arena used for horse shows, training, and riding lessons, and farm buildings filling every corner, this has been a working ranch for the last 25 years. The primary dwelling was originally built as a barn but was converted into a 4-bedroom, 3-bath, 2,914 sq. ft. amazing home with windows looking out on the ranch as well as barn-high ceilings that give a spacious feeling to the heart of the house! Enjoy extreme comfort with cooling and heating mini-splits in every room! Wind down the rustic center spiral staircase to the mother-in-law style lower-level, where you'll find 2 of the bedrooms and the laundry room. Across from the main arena is the original home that is now a completely rebuilt cottage with a large attached studio... a great place for a ranch manager to live. The possibilities are endless with this versatile property!

61 Kee Rd, Makawao

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

$1,825,000

Discover Hokuula in the quaint town of Haliimaile, nestled on the gentle slopes of Haleakala, overlooking Maui’s world-renowned Northshore coastline. Expansive ocean and mountain views will greet you from this soon to be Upcountry community of 196-single family homes. Featuring contemporary architecture with six unique, 4-bedroom models on lots of approximately 7,500 to 10,000 square feet. Hokuula offers a variety of diverse floor plans in single and two-story designs. In addition, ohana dwellings are available on various lots, providing even more versatility. Each home has been thoughtfully designed. This single-story Floor Plan A home has 4 bedrooms and 3 bathrooms. Features include an open floor plan, 9 foot ceilings, split AC, rain gutters, covered lanai, attached two car garage. Highlighted amenities consist of stainless-steel appliances, double paned windows, soft close cabinetry. A walking path around the perimeter of the community will provide another way to enjoy the panoramic views from Hali?imaile. Located just a few minutes from the modern conveniences of Kahului as well as the quaint charms of Paia and Makawao. This is truly a unique opportunity to own your piece of paradise on Maui, a wonderful place to call home. Developer reserves the right to modify floor plans, elevations, specifications, features, and prices without prior notice. Square footage and room sizes are approximate. All renderings and floor plans are conceptual and are not intended to be an actual depiction of the home, driveway, or landscaping. Prices vary between floor plan and lot selections along with view corridors. Buyer and Buyer's Agent to conduct due diligence.

4 Beds ⋅ 3 Baths ⋅ 407512 MLS ⋅ Fee Simple Tenure

Discover Hokuula in the quaint town of Haliimaile, nestled on the gentle slopes of Haleakala, overlooking Maui’s world-renowned Northshore coastline. Expansive ocean and mountain views will greet you from this soon to be Upcountry community of 196-single family homes. Featuring contemporary architecture with six unique, 4-bedroom models on lots of approximately 7,500 to 10,000 square feet. Hokuula offers a variety of diverse floor plans in single and two-story designs. In addition, ohana dwellings are available on various lots, providing even more versatility. Each home has been thoughtfully designed. This single-story Floor Plan A home has 4 bedrooms and 3 bathrooms. Features include an open floor plan, 9 foot ceilings, split AC, rain gutters, covered lanai, attached two car garage. Highlighted amenities consist of stainless-steel appliances, double paned windows, soft close cabinetry. A walking path around the perimeter of the community will provide another way to enjoy the panoramic views from Hali?imaile. Located just a few minutes from the modern conveniences of Kahului as well as the quaint charms of Paia and Makawao. This is truly a unique opportunity to own your piece of paradise on Maui, a wonderful place to call home. Developer reserves the right to modify floor plans, elevations, specifications, features, and prices without prior notice. Square footage and room sizes are approximate. All renderings and floor plans are conceptual and are not intended to be an actual depiction of the home, driveway, or landscaping. Prices vary between floor plan and lot selections along with view corridors. Buyer and Buyer's Agent to conduct due diligence.

179 Maiaku St Unit Lot 165, Makawao

Listing courtesy of Island Sotheby's International Realty(L).

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