Up Country Real Estate Search

Up Country Properties between $1,000,000 and $2,000,000 for Sale

Our website features the best real estate search for between $1,000,000 and $2,000,000 properties available in Up Country and surrounding areas. It is the only site you will ever need! It is easy-to-use and updated by the official REALTOR®’s database every 15 minutes. 

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Newest Up Country Properties between $1,000,000 and $2,000,000 for Sale

$1,150,000
2 Beds 1 Baths 410747 MLS ACTIVE Status
Discover the possibilities with this captivating 2-bedroom, 1-bathroom cottage situated on a little over half an acre of flat, fully usable land. Built in 2013, this well-maintained property was thoughtfully updated in 2022 with a remodeled kitchen and luxury vinyl plank flooring throughout. Enjoy gorgeous ocean views from the patio and beautiful mountain views throughout the property. The cottage features stainless steel appliances, split A/C in the primary bedroom and living room, a solar water heater, and 25 owned photovoltaic panels for added energy efficiency. The expansive lot offers plenty of room to enjoy the outdoors while providing significant future potential. The property also includes a small wood-frame shed for additional storage. The high-capacity septic system was intentionally designed to accommodate the future addition of up to a 5-bedroom home, offering flexibility for expansion along with a concrete tank and leech field. There is ample room to add a main house and potentially another cottage, subject to County approvals, permitting, zoning, and applicable regulations. Recent improvements include new exterior paint, adding to the property's inviting appeal. Whether you're looking for a comfortable cottage, additional space for future development, or a property with room to grow, this unique offering provides an exciting combination of usable land, views, solar infrastructure, and potential. Some photographs have been virtually staged for illustrative purposes.

284 Alalani St, Makawao

Listing courtesy of Shore To Shore Realty, Inc..

$1,100,000
3 Beds 2 Baths 410627 MLS ACTIVE Status
Welcome home to 742 Kekona Place, tucked into the heart of Makawao. If you love the charm of country living, the sense of community that comes with a small town, & the convenience of being approximately 20 minutes from the beach, this Upcountry home offers a wonderful blend of it all. Thoughtfully maintained and beautifully updated, 742 Kekona Place is a home where the attention to detail is immediately apparent. The kitchen was refreshed in 2026 with quartz countertops, high-end cabinetry, new lighting fixtures, & a bespoke backsplash inspired by the colors & movement of the sea. Automatic blinds add another thoughtful touch, bringing both convenience and a clean, modern feel to the home. The 500+ sqft garage has been transformed into the ultimate hangout space, creating an incredible extension of the home & an easy connection between indoor and outdoor living. Whether used as a game room, home gym, workshop, entertaining space, or the ultimate "mancave," it adds flexibility and plenty of room to spread out. Outside is where this property truly comes to life. Tropical landscaping, hot tub, ambient lighting, & multiple seating areas create a private backyard oasis that feels especially magical in the evenings. The front lanai wraps around the side of the home, offering even more space to relax outdoors, while a high-end fence accented with beautiful lighting adds privacy & a polished, resort-like feel. The location is equally special. Enjoy fast access to Makawao town with new sidewalks being built, as well as nearby Eddie Tam Park where a new playground is also being added. The Makawao Rodeo grounds are closeby too, putting some of Upcountry’s best-loved community spots right at your fingertips. Every corner of 742 Kekona Place has been thoughtfully enhanced with an eye toward comfort, function, & the smallest details. Come experience this special home for yourself & feel the magic of Makawao.

742 Kekona Pl, Makawao

Listing courtesy of Coldwell Banker Island Prop-Ku.

$1,569,500
3 Beds 3 Baths 410602 MLS ACTIVE Status
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).

$1,145,000
4 Beds 3 Baths 410550 MLS ACTIVE Status
Welcome to 30 Paha‘a Place, a beautifully updated and exceptionally versatile Upcountry Maui home tucked away on a flag lot at the end of a quiet cul-de-sac in Pukalani. Situated on approximately ¼ acre, this private property offers generous indoor and outdoor living, a flexible floor plan, mature landscaping and numerous recent improvements, including nearly 1000 additional square feet of unpermitted bonus rooms with peekaboo ocean views from the backyard and Haleakala views from the front yard. The bright and refreshed main residence features new interior paint and numerous updated doors, fixtures and finishes. The well-appointed kitchen offers cherry cabinetry, granite countertops, stainless steel appliances and gas cooking. Photovoltaic solar panels, solar hot water and seven split-system A/C units add comfort and energy efficiency throughout the property. A converted garage now serves as a spacious bonus room/gym with Murphy bed, offering flexible possibilities for recreation, work or guests. The attached nohana space has also been substantially upgraded with a remodeled kitchen and bathroom, stacked washer/dryer and an enclosed former porch creating additional usable library space. Outside, a newly stained deck and patio overlook the spacious, fully fenced yard shaded by mature fruit trees, with two sheds providing additional storage and garden space. Conveniently located near Pukalani and Makawao shopping, schools, parks and Upcountry amenities, and approximately 15 minutes from Kahului and the North Shore, 30 Paha‘a Place offers the space, flexibility and relaxed lifestyle that make Upcountry Maui living so special. Private. Updated. Versatile. Energy-conscious. And ready for its next chapter.

30 Pahaa Pl, Makawao

Listing courtesy of Keller Williams Realty Maui-Ka.

$1,350,000
6 Beds 4 Baths 410242 MLS ACTIVE Status
Tucked away on a peaceful private road, 35 Pukiki Place presents a rare opportunity to enjoy the best of Upcountry Maui living in one of the island’s most desirable microclimates. Recently renovated, this expansive 6 bedroom, 4 bathroom residence captures refreshing trade winds, beautiful ocean and North Shore views, and the privacy and tranquility that make this area so special. This two-story home’s greatest asset is its remarkably versatile floor plan, thoughtfully designed to provide exceptional separation of living spaces, with separate entrances for both levels, that feels like getting two homes for the price of one. Whether accommodating multigenerational living, extended family, long-term guests, a private home office, creative studio, fitness space, or simply providing room for everyone to spread out, the possibilities are endless. Indoor and outdoor spaces blend seamlessly, creating an inviting setting for entertaining, gathering with family and friends, or enjoying peaceful mornings and cool Upcountry evenings surrounded by nature. The fenced yard offers ample room for pets, gardening, outdoor recreation, or creating your own private sanctuary. Recently CPR’d and move-in ready, this property offers flexibility rarely found in today’s market. Conveniently located just minutes from Makawao Town’s acclaimed restaurants, cafes, boutiques, and renowned art galleries, while also providing easy access to Seabury Hall, Carden Academy, Montessori School of Maui, and many of the island’s premier public and private schools. Whether you’re seeking room to grow, a flexible layout to fit your evolving lifestyle, or simply a peaceful retreat with room for everyone, 35 Pukiki Place delivers an exceptional combination of space, comfort, privacy, and convenience in one of Upcountry Maui’s most coveted locations. Experience the side of Maui where life slows down. This is a CPR Residential condo Unit #A.

35 Pukiki Pl Unit A, Makawao

Listing courtesy of Coldwell Banker Island Prop(S).

$1,325,000
2 Beds 2 Baths 410052 MLS ACTIVE Status
Now offering a $20,000 buyer credit at closing! Looking for a home with multi-generational living options or a mortgage helper? Look no further than 191 Alohilani. This two-bedroom, two-bath home and two-bedroom, one-and-a-half-bath cottage offer the perfect setup and much more. The well-cared-for main home includes a covered, screened lanai with ocean and mountain views, an owned solar system to keep electric bills down, and a flex room that could serve as a third bedroom, hobby room, or home office. 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, kalo (taro), 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 d 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.

$1,999,000
4 Beds 3 Baths 409809 MLS ACTIVE Status
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.

$1,100,000
3 Beds 3 Baths 409260 MLS ACTIVE Status
Pukalani Fairway Estates – Unit #5 offers a rare blend of Upcountry charm, privacy, and natural beauty in one of Pukalani’s most desirable communities: 24 homes nestled on the greens of the Pukalani Golf Course. This 3-bedroom, 2.5-bath single-family Residential Condo is uniquely positioned to capture stunning views of Mauna Kahalawai and the central valley creating a serene backdrop to everyday living. The upper level features an open-concept design with vaulted ceilings and abundant natural light, flowing to a spacious lanai—perfect for relaxing or entertaining. The sellers have installed concrete steps and railings leading from the garage to the yard below. The house foyer is enclosed - allowing entrance from the garage directly into the home. The lower level includes three bedrooms and access to a truly special outdoor space. The entire yard has been thoughtfully planted with native Hawaiian plants and enhanced with garden paths creating a park like retreat. Enjoy being among o'hia and other native plants and alongside the rare yellow hibiscus (ma'o hau hele), Hawaii’s State Flower. The primary suite offers an ensuite bath, dual vanity, and walk-in closet. Additional highlights include a 2-car garage with full-sized laundry. Easy access to the golf course, shops, Farmers Market, and restaurants. Listing is a Residential condominium.

2811 Liholani St Unit #5, Pukalani

Listing courtesy of REMAX Hawaii Maui.

$1,399,000
3 Beds 2 Baths 408348 MLS ACTIVE Status
Bring your vision to this peaceful Upcountry property nestled just below the cool cloud line of Upper Piiholo. Set on two (2) beautifully established acres, this three (3) bedroom two (2) bath home offers more than twenty six hundred (2600+) square feet of interior space along with views that create an inspiring backdrop for a thoughtful renovation. Native trees, tall pines, and fragrant eucalyptus surround this property, offering both privacy and a deep connection to the land. The home is ready for someone who appreciates character and craftsmanship and wants to restore it to its original charm. A generous wraparound deck already frames the exterior, inviting a seamless indoor and outdoor lifestyle. Inside, the main level features an open living, dining and kitchen area with vaulted ceilings and a striking stone accented fireplace. Two (2) bedrooms and a full bath completes this floor. The primary suite rests on the upper level, offering treetop views and natural light. The finished basement offers a one (1) car parking garage and a large room, perfect for a home office, home theatre or possibly a work out/yoga studio. With internet available and plenty of room to reimagine both indoor and outdoor spaces, this property is a rare opportunity to create something truly special. Whether you update the existing layout or transform it into a more modern Upcountry retreat, the setting and foundation are already in place. This much loved home is waiting for its next chapter.

2400 Piiholo Rd, Makawao

Listing courtesy of Coldwell Banker Island Prop(Ka).

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