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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.

$725,000

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.

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.

$1,025,000

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.

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.

$2,641,000

Enjoy cool upcountry breezes, bicoastal views and the convenience of nearby Makawao Town in this thoughtfully upgraded ranch style residence. Situated in a gated community on a peaceful cul-de-sac, this home showcases quality upgrades and timeless finishes throughout including; cherry wood cabinetry, soft close drawers, gas cooktop, double ovens, new dishwasher and quartz countertops blending warmth and functionality. The home includes a gas fireplace, gas tankless water heater, 15 PV panels (leased, transferable to qualified buyer) and a Tesla charger delivering modern performance with island practicality. The outdoor space is equally inviting with established grapefruit, lemon and avocado trees. A beautiful home being offered furnished (with a separate bill of sale) , bring your personal touch and make 143 Lei‘ohu Circle your Maui Dream Home.

3 Beds ⋅ 3 Baths ⋅ 410991 MLS ⋅ Fee Simple Tenure

Enjoy cool upcountry breezes, bicoastal views and the convenience of nearby Makawao Town in this thoughtfully upgraded ranch style residence. Situated in a gated community on a peaceful cul-de-sac, this home showcases quality upgrades and timeless finishes throughout including; cherry wood cabinetry, soft close drawers, gas cooktop, double ovens, new dishwasher and quartz countertops blending warmth and functionality. The home includes a gas fireplace, gas tankless water heater, 15 PV panels (leased, transferable to qualified buyer) and a Tesla charger delivering modern performance with island practicality. The outdoor space is equally inviting with established grapefruit, lemon and avocado trees. A beautiful home being offered furnished (with a separate bill of sale) , bring your personal touch and make 143 Lei‘ohu Circle your Maui Dream Home.

143 Leiohu Cir, Makawao

Listing courtesy of Keller Williams Realty Maui-Ki.

$1,525,000

Discover Hoku’ula in the charming town of Haliimaile, set on the mild slopes of Haleakala and overlooking Maui’s famous North Shore. Construction is underway, with an estimated completion date of November 2026. Expansive ocean and mountain views will greet you from this bottom row, two-story C floor plan home with 4 bedrooms and 2.5 bathrooms. Features include; 9 foot ceilings, open layout, covered lanai, and an attached two car garage. Notable amenities include; split air-condition, rain gutters, stainless-steel appliances, double paned windows, soft close cabinetry, upgraded carpet, upgraded LVP flooring, Kohler tubs, sinks and toilets. Located just minutes from Kahului’s modern conveniences and the quiet appeal of Paia and Makawao. This is truly a unique opportunity to own your piece of paradise on Maui, a wonderful place to call home. All renderings and floor plans are conceptual and are not intended to be an actual depiction of the home, driveway, or landscaping. Square footage and room sizes are approximate. Buyer and Buyer's Agent to conduct due diligence.

4 Beds ⋅ 3 Baths ⋅ 410946 MLS ⋅ Fee Simple Tenure

Discover Hoku’ula in the charming town of Haliimaile, set on the mild slopes of Haleakala and overlooking Maui’s famous North Shore. Construction is underway, with an estimated completion date of November 2026. Expansive ocean and mountain views will greet you from this bottom row, two-story C floor plan home with 4 bedrooms and 2.5 bathrooms. Features include; 9 foot ceilings, open layout, covered lanai, and an attached two car garage. Notable amenities include; split air-condition, rain gutters, stainless-steel appliances, double paned windows, soft close cabinetry, upgraded carpet, upgraded LVP flooring, Kohler tubs, sinks and toilets. Located just minutes from Kahului’s modern conveniences and the quiet appeal of Paia and Makawao. This is truly a unique opportunity to own your piece of paradise on Maui, a wonderful place to call home. All renderings and floor plans are conceptual and are not intended to be an actual depiction of the home, driveway, or landscaping. Square footage and room sizes are approximate. Buyer and Buyer's Agent to conduct due diligence.

189 Hokupa St Unit Lot 36, Makawao

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

$1,475,000

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.

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).

$1,095,000

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 bonus living space with beautiful 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 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. Multiple avocado trees, fig, citrus, banana, lime, dragonfruit, pineapple and a bountiful spice garden offers options for additional income, or just to enjoy the bounties of island living. 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.

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 bonus living space with beautiful 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 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. Multiple avocado trees, fig, citrus, banana, lime, dragonfruit, pineapple and a bountiful spice garden offers options for additional income, or just to enjoy the bounties of island living. 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.

$1,495,000

Owner financing is possible! Discover a rare opportunity to own approximately 11.3 acres in the peaceful Hali’imaile/Makawao area. This private agricultural-zoned Lot A CPR parcel offers ocean and mountain views, cool breezes, and a true Upcountry ranch feel. Located within the Kaluanui Ridge 7-lot subdivision, the property is conveniently positioned between Makawao and Paia, with approximately a 5-minute drive in either direction. At an elevation of about 1200 ft this area reportedly gets an average of about 59 inches of rainfall per year and mostly sunny days all year round. This spacious property offers the privacy, open space, and quiet rural lifestyle that make Upcountry Maui so desirable. The land is mostly fenced and includes an approx. one-acre fenced animal pasture, making it well suited for livestock, farming, homesteading, or creating your ideal Maui country retreat. The lot also borders a drainage reserve, providing additional privacy and a natural buffer. Two existing container home dwellings are already in place. The larger dwelling features 4 bedrooms, a kitchen, bathroom, 40ft storage container, off-grid solar system with 21 PV panels, inverter setup, and roughly 14 kWh of 48V battery storage, and an 800-gallon water catchment system. The second container dwelling includes 2 bedrooms, 1 bathroom, kitchen, and catchment system, with power available by generator or from the main solar setup. Enjoy privacy, acreage, views, and the peaceful beauty of Maui’s Upcountry lifestyle—all while remaining close to town, beaches, schools, shops, and conveniences.

410547 MLS ⋅ Fee Simple Tenure

Owner financing is possible! Discover a rare opportunity to own approximately 11.3 acres in the peaceful Hali’imaile/Makawao area. This private agricultural-zoned Lot A CPR parcel offers ocean and mountain views, cool breezes, and a true Upcountry ranch feel. Located within the Kaluanui Ridge 7-lot subdivision, the property is conveniently positioned between Makawao and Paia, with approximately a 5-minute drive in either direction. At an elevation of about 1200 ft this area reportedly gets an average of about 59 inches of rainfall per year and mostly sunny days all year round. This spacious property offers the privacy, open space, and quiet rural lifestyle that make Upcountry Maui so desirable. The land is mostly fenced and includes an approx. one-acre fenced animal pasture, making it well suited for livestock, farming, homesteading, or creating your ideal Maui country retreat. The lot also borders a drainage reserve, providing additional privacy and a natural buffer. Two existing container home dwellings are already in place. The larger dwelling features 4 bedrooms, a kitchen, bathroom, 40ft storage container, off-grid solar system with 21 PV panels, inverter setup, and roughly 14 kWh of 48V battery storage, and an 800-gallon water catchment system. The second container dwelling includes 2 bedrooms, 1 bathroom, kitchen, and catchment system, with power available by generator or from the main solar setup. Enjoy privacy, acreage, views, and the peaceful beauty of Maui’s Upcountry lifestyle—all while remaining close to town, beaches, schools, shops, and conveniences.

2759 Baldwin Ave Unit A, Makawao

Listing courtesy of Hawaii Life (W).

$1,100,000

One of the most turnkey development opportunities in Upcountry Maui. This 1.8-acre vacant lot comes with its own three rare 5/8" county water meters and county-approved building plans for a main house with an attached ohana ready to break ground. Skip the years of waiting for the county, architectural fees, and uncertainty. Lot A is zoned R-3, which allows for a total of three homes of any size to be built. On level to gently sloping topography, the site offers sweeping views of the North Shore, Haleakala, and the West Maui Mountains. Tucked at the end of a quiet road, you get the peace of a private country setting while still being walking distance to the shops, restaurants, and charm of historic Makawao Town. Baldwin Beach is 10 minutes down the hill, and Costco and the airport are about 20 minutes away. At nearly 1,500 feet elevation, the weather is consistently cool and comfortable. Three water meters. R-3 zoning on nearly two acres. Approved plans in hand. Unit A of a 5.68 acre 3-unit CPR. The hidden gem you've been looking for!

410399 MLS ⋅ Fee Simple Tenure

One of the most turnkey development opportunities in Upcountry Maui. This 1.8-acre vacant lot comes with its own three rare 5/8" county water meters and county-approved building plans for a main house with an attached ohana ready to break ground. Skip the years of waiting for the county, architectural fees, and uncertainty. Lot A is zoned R-3, which allows for a total of three homes of any size to be built. On level to gently sloping topography, the site offers sweeping views of the North Shore, Haleakala, and the West Maui Mountains. Tucked at the end of a quiet road, you get the peace of a private country setting while still being walking distance to the shops, restaurants, and charm of historic Makawao Town. Baldwin Beach is 10 minutes down the hill, and Costco and the airport are about 20 minutes away. At nearly 1,500 feet elevation, the weather is consistently cool and comfortable. Three water meters. R-3 zoning on nearly two acres. Approved plans in hand. Unit A of a 5.68 acre 3-unit CPR. The hidden gem you've been looking for!

281 Maha Rd Unit Unit A, Makawao

Listing courtesy of Coldwell Banker Island Prop-Ku.

$550,000

Perched along desirable Alaluana Road in Olinda, this exceptional vacant parcel offers breathtaking mountain and ocean views in one of Upcountry Maui's most scenic locations. The dramatic sloped topography is enhanced by several terraces, creating visual interest and providing a unique setting for a custom home designed to complement the land's natural contours. The lower portion of the property is planted with renowned Hawaiian Koa hardwood trees, adding to the property's natural beauty and Upcountry character. Enjoy cool Olinda temperatures, spectacular sunsets, and panoramic vistas stretching from the slopes of Haleakala to the coastline. Overhead electricity is available, and catchment water systems are common in the area. Conveniently located just minutes from Makawao Town while offering the peace and privacy of Upcountry living. Buyer to conduct their own due diligence regarding water, utilities, building feasibility, grading requirements, access, and all development possibilities.

410167 MLS ⋅ Fee Simple Tenure

Perched along desirable Alaluana Road in Olinda, this exceptional vacant parcel offers breathtaking mountain and ocean views in one of Upcountry Maui's most scenic locations. The dramatic sloped topography is enhanced by several terraces, creating visual interest and providing a unique setting for a custom home designed to complement the land's natural contours. The lower portion of the property is planted with renowned Hawaiian Koa hardwood trees, adding to the property's natural beauty and Upcountry character. Enjoy cool Olinda temperatures, spectacular sunsets, and panoramic vistas stretching from the slopes of Haleakala to the coastline. Overhead electricity is available, and catchment water systems are common in the area. Conveniently located just minutes from Makawao Town while offering the peace and privacy of Upcountry living. Buyer to conduct their own due diligence regarding water, utilities, building feasibility, grading requirements, access, and all development possibilities.

Alaluana Rd, Makawao

Listing courtesy of Hawaii Life (MA).

$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).

$1,195,000

This super charming 5-bedroom, 2.5-bathroom home in Pukalani is set on nearly 14,000 sq.ft., the property showcases sweeping 180-degree ocean and mountain views from its expansive lanai, kitchen, and the primary bathroom's vintage tub! The generous fenced grounds—including a permitted 80-foot shed, large yard, and fruit trees—provide ample space to relax, entertain, or play, while an outdoor shower enhances the island lifestyle. A newly installed 1500-gallon septic system is a very valuable improvement for future owners on Maui! Ideally located near parks, shopping, trendy Upcountry eateries, and the popular Saturday farmers market, this timeless haven blends views, open-air living, opportunity, versatility, and location convenience. Layout and square footage may differ from tax records. Bring your vision to life! Call your realtor, easy to see!

5 Beds ⋅ 3 Baths ⋅ 410149 MLS ⋅ Fee Simple Tenure

This super charming 5-bedroom, 2.5-bathroom home in Pukalani is set on nearly 14,000 sq.ft., the property showcases sweeping 180-degree ocean and mountain views from its expansive lanai, kitchen, and the primary bathroom's vintage tub! The generous fenced grounds—including a permitted 80-foot shed, large yard, and fruit trees—provide ample space to relax, entertain, or play, while an outdoor shower enhances the island lifestyle. A newly installed 1500-gallon septic system is a very valuable improvement for future owners on Maui! Ideally located near parks, shopping, trendy Upcountry eateries, and the popular Saturday farmers market, this timeless haven blends views, open-air living, opportunity, versatility, and location convenience. Layout and square footage may differ from tax records. Bring your vision to life! Call your realtor, easy to see!

84 Kilakila Pl, Makawao

Listing courtesy of eXp Realty.

$4,400,000

Located in Baldwin Ranch Estates, this property is a refined expression of contemporary plantation coastal design, where timeless architecture and effortless indoor-outdoor living come together against a backdrop of sweeping ocean and West Maui Mountain views. Designed by Jeff Lundahl, the residence is oriented to capture Maui's natural beauty from nearly every room, with expansive pocketing doors opening to an oversized covered lanai that becomes a seamless extension of the living space. The gated entry to resort-inspired grounds are designed for both relaxation and entertaining, featuring a sparkling pool, a pool cabana with a lounge area, a bathroom, and an outdoor shower, all surrounded by beautifully landscaped living areas that embrace Maui's year-round climate. A spacious three-bay garage of more than 1,000 square feet includes versatile air conditioned flex space and a bathroom, providing options for a home gym, workshop, creative studio, and additional storage for surfboards, bikes, and other North Shore pursuits. Positioned between the charming boutiques and cafés of Makawao and the vibrant beaches and lifestyle of Paia, this exceptional property has refreshing trade winds, panoramic vistas, and convenient access to some of Maui's most sought-after schools, world-class beaches and connections to Maui's North Shore lifestyle. The is Unit B of a CPR.

2 Beds ⋅ 3 Baths ⋅ 410147 MLS ⋅ Fee Simple Tenure

Located in Baldwin Ranch Estates, this property is a refined expression of contemporary plantation coastal design, where timeless architecture and effortless indoor-outdoor living come together against a backdrop of sweeping ocean and West Maui Mountain views. Designed by Jeff Lundahl, the residence is oriented to capture Maui's natural beauty from nearly every room, with expansive pocketing doors opening to an oversized covered lanai that becomes a seamless extension of the living space. The gated entry to resort-inspired grounds are designed for both relaxation and entertaining, featuring a sparkling pool, a pool cabana with a lounge area, a bathroom, and an outdoor shower, all surrounded by beautifully landscaped living areas that embrace Maui's year-round climate. A spacious three-bay garage of more than 1,000 square feet includes versatile air conditioned flex space and a bathroom, providing options for a home gym, workshop, creative studio, and additional storage for surfboards, bikes, and other North Shore pursuits. Positioned between the charming boutiques and cafés of Makawao and the vibrant beaches and lifestyle of Paia, this exceptional property has refreshing trade winds, panoramic vistas, and convenient access to some of Maui's most sought-after schools, world-class beaches and connections to Maui's North Shore lifestyle. The is Unit B of a CPR.

2350 Baldwin Ave Unit B, Makawao

Listing courtesy of Hawaii Life (W).

$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.

$1,725,000

Discover Hoku’ula 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. Hoku’ula 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 upstairs living F floor plan home has 4 bedrooms and 2.5 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 ⋅ 407513 MLS ⋅ Fee Simple Tenure

Discover Hoku’ula 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. Hoku’ula 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 upstairs living F floor plan home has 4 bedrooms and 2.5 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.

139 Maiaku St Unit Lot 168, Makawao

Listing courtesy of Island Sotheby's Int'l Rlty(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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