Maui Homes with Detached Ohana Cottage

5 Beds ⋅ 3 Baths ⋅ 410440 MLS ⋅ Fee Simple Tenure

33 Hana Highway | An Iconic Legacy Estate on Maui's North Shore There are properties that come to market, and there are properties that define a coastline. Welcome to 33 Hana Highway, an extraordinary beachfront estate in the heart of Paia, offering an exceptionally rare 145 linear feet of pristine white sand beach frontage along one of Maui's most celebrated shorelines. Offered at its July 2026 appraised valued of $13,300,000, this is more than a home—it is an irreplaceable legacy estate where the true luxury lies in the land, the shoreline, and the privilege of ownership. With an unparalleled connection to the Pacific, the residence embraces the timeless character of Maui's North Shore. Thoughtfully designed to complement its spectacular setting, the home captures the relaxed elegance that has long defined Paia—a place where sophistication is measured not by excess, but by authenticity, privacy, and an effortless indoor-outdoor lifestyle. Expansive lanais, light-filled living spaces, and panoramic ocean vistas invite year-round entertaining, quiet reflection, and unforgettable gatherings with family and friends. Beyond the residence, the grounds unfold into a remarkable oceanfront sanctuary framed by mature tropical landscaping, generous lawn areas, and direct access to an expansive stretch of soft white sand. With 145 feet of linear beachfront, the property commands a presence that is increasingly impossible to replicate. This remarkable shoreline offers an extraordinary sense of space, privacy, and permanence rarely found in Hawaii's oceanfront market. Located just moments from the vibrant charm of Paia Town, owners enjoy effortless access to award-winning restaurants, artisan boutiques, renowned galleries, world-class surfing, and the relaxed rhythm that has made Maui's North Shore one of the world's most desirable coastal destinations. Here, every day begins with sunrise over the Pacific and ends with the sound of waves meeting the shore. Properties of this significance are seldom offered. As available beachfront continues to diminish, estates with substantial sandy frontage have become true generational holdings—assets that are acquired with intention and passed forward with pride. Whether preserved in its timeless island character or thoughtfully reimagined into a world-class coastal residence, the intrinsic value will always remain rooted in what can never be recreated: the land, the location, and the extraordinary shoreline. Property Highlights • Recently appraised at $13,300,000 • Approximately 145 linear feet of pristine white sand beach frontage • Exceptional oceanfront estate in the heart of Paia • Expansive Pacific Ocean and coastline views • Authentic island architecture designed for seamless indoor-outdoor living • Mature tropical landscaping and spacious beachfront grounds • Direct access to one of Maui's most desirable sandy beaches • Minutes from Paia's acclaimed restaurants, boutiques, galleries, and North Shore lifestyle • A truly rare legacy estate with enduring generational value Some homes are built. Others become part of Hawaii's history. 33 Hana Highway is one of the few addresses where legacy begins at the shoreline. LLC Member holds an ownership interest in the property. Member is an inactive Realtor in the State of Hawaii.

33 Hana Hwy, Paia

Listing courtesy of The Agency Maui.

$2,395,000

3 Beds ⋅ 2 Baths ⋅ 410327 MLS ⋅ Fee Simple Tenure

Wow! Bi-coastal views from Molokini to Paia! This perfectly positioned home and ohana on 1/2 acre of land, in the highly desirable Kula Mala neighborhood, features privacy, convenience, and quality construction. The homes feature stucco exteriors, tile and copper roofing, an owned photovoltaic system, and quality materials throughout. The oversized garage features a grand rooftop lanai with bi-coastal views, including Molokini, Kahoolawe, Lanai, Molokai, the West Maui Mountains, and Haleakala, for sunset entertaining and stargazing. Bonus, permitted 364 sq/ft space perfect for a gym, yoga space, or home office is in addition to the home's 2674 square feet. The built in custom closet in the primary bedroom, kitchen pantry, fireplace, outdoor shower, huge family/game room (with ground floor outdoor entertaining space), and beautiful rock walls are just some of the features that make this home special. The ohana has its own separate driveway and parking, while the main home has an elegant gated entry providing privacy and security. Please do not disturb the ohana tenants. Mahalo.

56 Lopaka Pl, Kula

Listing courtesy of Haleakala Realty, LLC.

$4,500,000

2 Beds ⋅ 2 Baths ⋅ 410325 MLS ⋅ Fee Simple Tenure

Laulea is often translated as “peace and friendship,” which feels particularly appropriate for one of Spreckelsville’s most desirable private roads. Set on just under one-third of an acre, this inviting house and cottage property captures the relaxed character of Maui’s North Shore. The two-bedroom, two-bath main home was completely rebuilt in 1996 with style, warmth, and distinctive details, including seashell relief work, bamboo accents, and ohia posts. Skylights, open-truss ceilings, and an open kitchen and living area fill the home with natural light, while two spacious covered lanais extend the living space outdoors and create inviting settings for dining, relaxing, and gathering with friends. Built in 2005, the elevated cottage has its own Balinese-inspired character, with merbau wood and travertine floors, vaulted ceilings, Venetian plaster, and thoughtful architectural touches throughout. A flexible bonus space below the cottage provides additional room for a home office, gym, studio, storage, or other uses. The lovely backyard and two outdoor showers are perfectly suited to life near the beach. Multiple beaches and surf spots are nearby, along with Maui Country Club, Kaunoa Senior Center, Pa?ia, and convenient access to OGG, Whole Foods, and Costco. Peaceful, private, and full of personality, this is a special little compound in one of the North Shore’s most sought-after neighborhoods.

450 Laulea Pl, Paia

Listing courtesy of The Maui Real Estate Team Inc.

$2,349,000

6 Beds ⋅ 9 Baths ⋅ 410318 MLS ⋅ Fee Simple Tenure

Market Rental income $20,000/mo. Main home is a rectangle with courtyard in the middle. Studio units surround the courtyard with covered egress. All units were remodeled in 2019. New Roof, Laminate floors, All Hard Wood Cabinets and Granite counter tops. Please DO NOT DISTURB Tenants and DO NOT WALK property without listing agent present. Some aspects of property are non-conforming.

50 Hoonani St, Kihei

Listing courtesy of Pacific Shores Realty.

$2,350,000

3 Beds ⋅ 3 Baths ⋅ 410282 MLS ⋅ Fee Simple Tenure

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

68 Ka Dr, Kula

Listing courtesy of Compass-W.

$2,095,000

3 Beds ⋅ 3 Baths ⋅ 410263 MLS ⋅ Fee Simple Tenure

Welcome to your private oasis at 4345 Waha Place! Nestled on 2 usable, level acres just off Hana Highway, this exceptional property offers unparalleled privacy and tranquility. The newly renovated two-story main residence features three bedrooms and three bathrooms, thoughtfully updated with modern comfort and timeless style. Beautiful hardwood flooring flows throughout the home. Fresh interior and exterior paint, updated lighting, and upgraded hardware complete this move-in-ready retreat. Adding to the property's versatility is a detached two-bedroom, two-bath Ohana with an 870-square-foot garage. The Ohana exudes warmth with soft, neutral finishes, vaulted ceilings, skylights, and expansive windows that fill the home with natural light. Its inviting living area provides the perfect place to relax. Surrounded by lush tropical landscaping, great avocados, mangoes, and bananas tucked away at the base of a Pu'u, the expansive grounds create an inspiring setting for creativity, entertaining, or simply enjoying Maui's peaceful lifestyle. With multiple living spaces, abundant usable land, and exceptional privacy, this property is much more than a home, it's a sanctuary. Don't miss the opportunity to own this unique Maui retreat.

4345 Waha Pl, Haiku

Listing courtesy of Coldwell Banker Island Prop(S).

$1,900,000

3 Beds ⋅ 3 Baths ⋅ 410160 MLS ⋅ Fee Simple Tenure

Located in the highly desirable neighborhood of Maui Meadows, 3248 Akala Drive offers a spacious and well maintained property situated on a beautifully landscaped ½-acre lot. The thoughtfully updated main residence features a wraparound deck with ocean views, a PV system, and a tile roof. The main home offers a flexible floor plan with the primary suite, additional bedroom, full bathroom, kitchen, and living area located upstairs. The kitchen is beautifully appointed with granite countertops, wood cabinetry, tile finishes, and stainless steel appliances. The lower level includes an additional bedroom, full bathroom, and family room, providing added space for guests, family, or a home office. Also located on the lower level is a one-bedroom, one-bath ohana with a private entrance and lanai, offering excellent versatility for guests, extended family, or rental potential. A detached one-bedroom, one-bath cottage at the front of the property features its own private and spacious covered outdoor living area. With a single-car garage and ample additional parking, this property provides the space and flexibility. Whether you are looking for multi-generational living, rental opportunities, or your own private island retreat, this property offers privacy, comfort, and the Maui lifestyle you've been waiting for.

3248 Akala Dr, Kihei

Listing courtesy of Coldwell Banker Island Prop(S).

$2,649,000

5 Beds ⋅ 4 Baths ⋅ 410159 MLS ⋅ Fee Simple Tenure

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

1740 Piiholo Rd, Makawao

Listing courtesy of Coldwell Banker Island Prop(S).

$14,000,000

4 Beds ⋅ 4 Baths ⋅ 410153 MLS ⋅ Fee Simple Tenure

Set on beautifully curated grounds in Spreckelsville on Maui's North Shore, this extraordinary oceanfront estate embodies the timeless character of Old Hawaii, while offering a lifestyle centered around ocean, wellness, and understated luxury. Framed by sweeping views of the Pacific and peaceful bays stretching in both directions, the gated estate occupies one of the most breathtaking settings in Hawaii. A private pathway provides effortless access to a pristine white sandy beach lies just moments away. The compound features two tastefully renovated residences that honor their original plantation-era architecture while incorporating modern comforts and craftsmanship. The main home's four en suite bedrooms, inviting gathering spaces, and beautifully appointed chef's kitchen were designed to bring family and friends together, creating an atmosphere that is both sophisticated and welcoming. There's also a detached ohana perfect for guests or a caretaker. Life here revolves around connection—to nature, community, and the sea. World-class wingfoiling, kitesurfing, surfing, paddling, cycling, and beach walks await just beyond the property. The nearby Maui Country Club with golf, tennis and pickelball have further elevated Spreckelsville as one of Hawaii's most desirable coastal communities for those who embrace an active and healthy lifestyle.

477 Laulea Pl, Paia

Listing courtesy of Hawaii Life (W).

$3,950,000

3 Beds ⋅ 4 Baths ⋅ 410135 MLS ⋅ Fee Simple Tenure

Located inside the Ka'anapali Golf Estates, 23 Kahuakai Place includes a 3-bedroom, 4-bath, 3,145 sq. ft. luxury home, and a 600 sq. ft. 1-bedroom Ohana unit. The property offers incredible amenities, including an incredible private pool and lanai space. Entering the home's expansive foyer, natural light dances through large windows, illuminating the exquisite craftsmanship and attention to detail showcased throughout, including Mahogany pocket doors and trim, slate floors, and wood-lined recessed ceilings with fans. A wall of pocket doors connects the Great Room with the inner pool and hot tub lanai at the heart of the home, allowing for seamless Hawaiian-style indoor-outdoor living. The spacious lanai features both covered and open spaces. The centerpiece is a breathtaking salt-water pool and hot tub that sparkle under the warm Hawaiian sun. The entire space is backed by a natural privacy wall of lush tropical foliage and swaying palm trees, creating a signature Hawaiian look. As the day transitions into night, the space transforms into a magical setting with gas tiki torches and atmospheric pool lighting. Dine under the covered areas day or night, rain or shine, or simply lounge on comfortable seating and listen to the gentle breeze rustling through the tropical foliage. An additional full bath is directly accessible from the pool area. The gourmet kitchen features custom cabinetry, matching top-of-the-line SubZero appliances, a dual-compartment dishwasher, gorgeous granite counters, and a generously sized island for casual meals and socializing during meal prep. The home has three beautiful bedrooms, including one guest suite on the ground floor and a Primary bedroom and additional guest suite on the second floor. All the bathrooms are refreshed and feature Grove plumbing fixtures by Kohler. The ground-floor guest suite has direct lanai access and a full en-suite bath with a walk-in shower. The bathroom design uses the same quality granite counters as the kitchen and a bamboo frosted glass screen—gorgeous tiling ties in with the rest of the home. A beautiful wood staircase leads to the second floor, where one finds the Primary bedroom and a second guest suite. The stairwell is lit by frosted windows featuring a bamboo motif, providing privacy and a consistent design theme as you move throughout the home. Upstairs, one finds the luxurious Primary suite, a true oasis of tranquility. Its spacious layout and ocean views offer the perfect sanctuary to unwind after a long day. The en-suite bathroom is a spa-like retreat, boasting a corner jacuzzi tub, a walk-in shower, and dual vanities; a massive walk-in closet provides ample room for wardrobe and storage. The suite also features a nook that can serve as a yoga, reading or workspace. In the bedroom, sliding glass doors open to a private covered lanai ideally positioned to appreciate the stunning ocean views - it's the perfect place for a morning coffee or afternoon reading. The brightly lit and spacious third guest room also has a private bathroom with a walk-in shower. In addition, the home has a three-zone AC, an alarm system, audio speakers, and a two-car garage with storage. 23 Kahuakai Place also has a 1-bedroom, 1-bath, 600 sq. ft. Ohana unit that is perfect for visiting friends and family. The Ohana features the same high-end cabinetry as the main home, a carport, washer and dryer, and a lanai with ocean views. Take advantage of this opportunity to own a charming home with in-demand features. 23 Kahuakai Place is ideally designed for entertaining guests or spending quality time with loved ones. In addition, residents enjoy golf-cart access to the Ka'anapali Resort, making this the ultimate Maui retreat!

23 Kahuakai Pl, Lahaina

Listing courtesy of Welcome Hawaii Properties.

$16,950,000

5 Beds ⋅ 6 Baths ⋅ 410130 MLS ⋅ Fee Simple Tenure

Perched on Maui’s coveted west side, this extraordinary 8-bedroom private estate offers a level of luxury, privacy, and craftsmanship rarely seen in Hawai'i. More than a home, this is a legacy estate, an irreplaceable Maui sanctuary designed for those who accept nothing less than extraordinary. Located in the coveted Plantation Estates at Kapalua community on the incredible 16th hole of the world-class Plantation Course, the property commands unmatched sweeping panoramic views across the Pailolo Channel framed by the stunning views of the outer islands of Lana'i and Moloka'i. Designed without compromise, the 2-acre estate encompasses more than 8,200 square feet across two separate residences, creating a private retreat unlike any other. Resort-caliber amenities include an infinity-edge pool and dual spas, private office, theater and fitness center. The 7,200 square foot 5-bedroom 5.5 bath main residence seamlessly blends indoor and outdoor living through expansive custom pocket sliding doors that open to reveal breathtaking ocean vistas and unforgettable sunsets. Rich natural materials, custom African Mahogany millwork, exotic stone, and world-class finishes define every space, from the chef’s kitchen and grand great room to the spectacular primary suite. A fully appointed three-bedroom guest cottage with its own pool, fire-pit and Palapa set over a koi pond provides exceptional accommodations for family, guests, or staff while maintaining complete privacy. Aside from world-class golf, the Kapalua resort offer the utmost in amenities including award-winning spa, tennis and pickleball, exquisite dining options and some of the finest beaches: Fleming Beach, Oneloa Bay and Kapalua Bay, which was rated as the Best Beach in America by Conde Nast Travel Magazine.

706 Mokuleia Pl Unit 6, Lahaina

Listing courtesy of Keller Williams Realty Maui-L.

$2,395,000

5 Beds ⋅ 4 Baths ⋅ 409724 MLS ⋅ Fee Simple Tenure

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

15 Olinda Rd, Makawao

Listing courtesy of eXp Realty.

Maui Homes with Detached Ohana Cottage

Newest Maui Homes with Detached Ohana Cottage