Makawao/Olinda/Haliimaile Homes with Fee Simple Land tenure

Makawao/Olinda/Haliimaile Homes with Fee Simple Land tenure

Welcome to the enchanting neighborhoods of Makawao, Olinda, and Haliimaile, nestled in the lush, rolling hills of Maui, Hawaii. This picturesque region is a hidden gem that beautifully marries the charm of old Hawaii with the vibrancy of modern living. Known for its cool climate and breathtaking views, these neighborhoods offer a serene escape from the bustling beaches, while still being just a short drive from the coast.

Makawao, a historic paniolo (cowboy) town, is rich in culture and tradition. Stroll through its quaint streets lined with art galleries, boutique shops, and delightful eateries that showcase local flavors. The annual Makawao Rodeo draws visitors from all over, celebrating the town’s cowboy heritage. Just a stone's throw away, Olinda boasts stunning vistas and an abundance of lush greenery, making it a nature lover's paradise. Hiking trails weave through the area, leading you to breathtaking lookout points and the vibrant flora of Maui's highlands.

Haliimaile, known for its friendly community atmosphere, is home to charming residences that often come with fee simple land tenure, providing homeowners with full ownership and peace of mind. This feature is particularly appealing for those seeking stability and a sense of belonging in this idyllic locale.

Whether you're looking for a cozy cottage or a spacious family home, the Makawao, Olinda, and Haliimaile neighborhoods offer a unique blend of tranquility, community spirit, and natural beauty. Experience the best of island living in these enchanting Maui neighborhoods, where every day feels like a vacation!

Newest Makawao/Olinda/Haliimaile Homes with Fee Simple Land tenure

$1,185,000
4 Beds ⋅ 3 Baths ⋅ 410811 MLS ⋅ Fee Simple Tenure
Makawao charm, privacy, and versatility, all within walking distance of town. Located on Piikea Place, a quiet cul-de-sac, this remodeled and well-maintained property features a 4-bedroom, 2.5 bath main home, plus a legal, attached 600 sf ohana with its own entrance, kitchenette, and bathroom. The main home's open-plan kitchen and living area make it easy to prepare meals while remaining part of the conversation. The kitchen features a gas stove and bar counter for casual dining and gathering. A 400+ sf enclosed lanai with vaulted, open-beam ceilings provides additional flexible living space. The home also includes a dedicated laundry area, gas dryer, and solar water heater. The versatile layout offers several possibilities: live in the main home and rent the ohana, accommodate extended family or guests, or use the entire property for rental income. Outside, lush landscaping creates a sense of privacy and tranquility. The fully fenced backyard features two raised garden beds, a gazebo, surfboard racks, and two storage sheds. Five on-site parking spaces, plus ample street parking, make coming and going easy for residents and guests. The property is currently tenant-occupied. Please do not disturb the tenants. Showings are available by appointment only.

3650 Piikea Pl, Makawao

Listing courtesy of Compass-W.

$1,599,000
4 Beds ⋅ 2 Baths ⋅ 410773 MLS ⋅ Fee Simple Tenure
Over two acres on Makawao Avenue, held by the same owners for generations. The property sits up on a rise in the band between Pukalani and Makawao, with Haleakala above it and open sky in every direction. Cool mornings, usable ground, and a location that needs no explaining to anyone who knows upcountry. The parcel is zoned agricultural and largely open. Room for pasture, orchard, gardens, animals, or equipment, with space left over. A 4 bedroom, 2 bath home sits on the property and is ready to live in now. Makawao town and the shops and restaurants along Baldwin Avenue are minutes away, with Kahului a short drive down the hill. Over two acres fronting Makawao Avenue rarely becomes available, and property held this long tends to sell once and stay put. Come see it in person, since the size and the setting read differently on the ground than they do in photos. Contact your agent to schedule a private showing.

640 Makawao Ave, Makawao

Listing courtesy of Keller Williams Realty Maui-Ka.

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

284 Alalani St, Makawao

Listing courtesy of Shore To Shore Realty, Inc..

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

742 Kekona Pl, Makawao

Listing courtesy of Coldwell Banker Island Prop-Ku.

$1,569,500
3 Beds ⋅ 3 Baths ⋅ 410602 MLS ⋅ Fee Simple Tenure
Tucked privately at the top of a cul-de-sac, this beautifully appointed 3-bedroom, 3-bath home plus office is a Makawao residence that offers a rare combination of thoughtful design, lush surroundings, private pool, intimate outdoor spaces, and an exceptionally flexible floor plan. The home feels both gracious and wonderfully easy to live in, with a sense of privacy and tranquillity that is increasingly difficult to find. Upstairs, an inviting living room is warmed by a cozy gas fireplace, while expansive windows draw in abundant natural light and frame the verdant surroundings. The kitchen and living spaces open naturally toward the home's vine-draped lanai on the lee side- the Owner's favorite place to gather, dine, and enjoy the sweet views toward Makawao sunsets. The spacious primary suite offers a private retreat, complete with built-in bookshelves and a serene sense of separation from the rest of the home. Downstairs feels like its own private world. Two additional bedrooms and an exceptionally generous second living room create a versatile configuration for guests, extended family, a home office, or live-in relatives. From the bedrooms, step directly onto your private lanai and toward the pool and gardens, creating an effortless connection to the outdoors. Outside, the beautifully landscaped grounds are designed for privacy and enjoyment. A fabulous intimate lap pool and cozy pool pavilion provides a peaceful focal point for this residence. For energy efficiency, the property is also equipped with 32 photovoltaic panels. The location is equally compelling. Enjoy the charm of Makawao town within walking distance, while Kahului and Baldwin Beach are approximately 20 minutes away. Here, thoughtful architecture, lush grounds, privacy, flexible living spaces, and an enviable Upcountry setting come together in a truly special property. A distinctive home with wonderful possibilities.

1102 Mailuna Pl, Makawao

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

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

30 Pahaa Pl, Makawao

Listing courtesy of Keller Williams Realty Maui-Ka.

$835,000
4 Beds ⋅ 2 Baths ⋅ 410447 MLS ⋅ Fee Simple Tenure
Warm 4-bedroom, 2-bath home in the heart of Makawao! Conveniently located within walking distance to schools, parks, shopping, and local restaurants, this property offers the charm of Upcountry living in a well-established neighborhood where neighbors know and care for one another. Situated on a quiet, private street, the home provides a peaceful setting while remaining close to everyday conveniences. This longtime family home has been expanded over the years, creating additional living space. The improvements were completed without permits, and county records do not reflect the current configuration. Buyers are advised to conduct their own due diligence regarding the property's condition, improvements, and county records. Property is served by county water, a cesspool, and county trash service. Open House: Sunday, August 9, from 10:00 AM to 2:00 PM. Come explore the possibilities this centrally located Makawao home has to offer!

3566 Kalua Pl, Makawao

Listing courtesy of Tri-Isle Rlty & Dev Co Inc.

$1,100,000
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.

$1,390,000
4 Beds ⋅ 4 Baths ⋅ 410393 MLS ⋅ Fee Simple Tenure
In the Hawaiian language, Iini means "to desire, yearn for, or long for"—a fitting introduction to this tastefully renovated 4-bedroom, 3.5-bath home with a new shingle roof conveniently located in Makawao. The well-designed floor plan places the spacious living and dining areas at the center of the home, separating two bedrooms on each side to provide both privacy and functionality. The remodeled kitchen features custom cabinetry, a gas range, and a convenient pass-through window to the outdoor dining area, making entertaining a breeze. This versatile space can also serve as a covered carport when desired. Recent upgrades include luxury vinyl plank flooring, split A/C throughout, instant water heater shared by primary bath and 2nd bedroom bath, and numerous thoughtful updates throughout. Beyond the dining area, the covered pavilion and expansive interlocking deck tile patio create an inviting outdoor retreat with plenty of room for relaxing, entertaining, or enjoying Makawao's comfortable Upcountry climate. 305 Iini Way—a home you'll be longing to come home to.

305 Iini Way, Makawao

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

$1,650,000
2 Beds ⋅ 2 Baths ⋅ 410267 MLS ⋅ Fee Simple Tenure
Follow the country road to the very top of Piiholo Road, where peaceful Upcountry living, privacy, and breathtaking surroundings await. Nestled on this exceptional 3 Acre property is a custom-crafted 2-bedroom bamboo home that blends natural beauty, sustainability, and timeless design. Bamboo is prized around the world for its strength, warmth, and renewable qualities, creating a truly unique living environment. A long ribbon driveway welcomes you to the home, where custom craftsmanship and thoughtful details create living spaces with views of the surrounding countryside and the ocean beyond. The property is well equipped with abundant potable water supplied by three 30,000-gallon water storage tanks, providing ample capacity for the home and agricultural uses. A spacious barn adds versatility, featuring a separate apartment and a large workshop currently used for woodworking. Whether you're looking for space to farm, create, work, or simply enjoy the Upcountry lifestyle, this property offers endless possibilities. An opportunity to own a private Maui property where craftsmanship, sustainability, and quiet country living come together. So peaceful!

156 Alaluana Rd, Makawao

Listing courtesy of Coldwell Banker Island Prop(P).

$999,000
2 Beds ⋅ 1 Baths ⋅ 410243 MLS ⋅ Fee Simple Tenure
Nestled on a private road, 37 Pukiki Place offers the peace, privacy, and tranquility that define Upcountry Maui living. This recently renovated single-level residence is located in one of Maui’s most sought-after microclimates, where cool trade winds, beautiful ocean and North Shore views, and a serene setting create an exceptional place to call home. Thoughtfully designed with an emphasis on indoor-outdoor living, the spacious 253 square foot covered lanai and enclosed carport provide the perfect space for entertaining, dining, or simply unwinding while enjoying the surrounding beauty. Recently CPR’d and complete with its own septic system, this move-in-ready home offers the ideal blend of comfort, functionality, and low-maintenance living. The fully fenced yard provides ample space for pets, gardening, and enjoying the Upcountry lifestyle, with room to create your own private oasis. Conveniently located just minutes from Makawao Town’s charming boutiques, local restaurants, cafés, and renowned art galleries, you’ll also appreciate easy access to Seabury Hall, Carden Academy, Montessori School of Maui, and many of the island’s top public and private schools. If you’ve been searching for the “right-sized” Upcountry home that combines privacy, convenience, breathtaking views, and a true sense of tranquility, 37 Pukiki Place delivers. This is a CPR Residential condo Unit #B.

37 Pukiki Pl Unit B, Makawao

Listing courtesy of Coldwell Banker Island Prop(S).

$1,350,000
6 Beds ⋅ 4 Baths ⋅ 410242 MLS ⋅ Fee Simple Tenure
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).

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