N. Shore Homes with Pool

Welcome to the enchanting North Shore of Maui, Hawaii, where paradise meets the perfect home. This stunning region is renowned for its breathtaking landscapes, pristine beaches, and vibrant local culture. The North Shore is a haven for outdoor enthusiasts, offering an abundance of activities such as surfing, hiking, and snorkeling in crystal-clear waters. With its lush greenery and dramatic coastal views, it's no wonder this area is a sought-after destination for both residents and visitors alike.

When it comes to finding your dream home in this idyllic location, you'll be delighted to discover a variety of properties that boast luxurious amenities, including private pools. Imagine stepping into your own backyard oasis, where you can unwind in the sun, host unforgettable gatherings, or simply enjoy a refreshing dip after a day of exploring the island. Homes with pools in the North Shore offer a unique blend of comfort and leisure, providing the perfect backdrop for a laid-back Hawaiian lifestyle.

As you explore the North Shore, you'll find charming towns like Paia and Haiku, each with its own unique character and vibrant community spirit. From trendy boutiques and art galleries to delicious farm-to-table dining experiences, the local culture is rich and inviting. With easy access to world-renowned surf spots and stunning natural wonders, living in this region means embracing the best that Maui has to offer.

Whether you're looking for a tranquil retreat or a family-friendly home, the North Shore of Maui awaits you with open arms. Dive into the island lifestyle and make your dream of owning a home with a pool in this tropical paradise a reality!

Newest N. Shore Homes with Pool

$4,400,000

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).

$2,880,000

4 Beds ⋅ 3 Baths ⋅ 410015 MLS ⋅ Fee Simple Tenure

Exceptional Ocean Vistas amidst your tropical paradise estate on Maui's famed North Shore. Affectionately coined, "Hale O Peahi" this expansive custom crafted estate offers unlimited potential on a seamless level on an open facing lanai that flows out to the like-new saline pool and spa. Nestled in the highly desirable and exclusive Peahi Hui Land Subdivision on Maui's breathtaking North Shore. This expansive single-family residence offers a tranquil, elevated retreat on a generous 2-acre estate blessed with stunning ocean and mountain views from this exceptional gated estate.Hale O Peahi offers sophisticated single-level living with exceptional privacy and views. Boasting 3,576 sq ft of living space, the home features 4 bedrooms, 2.5 baths, and “pod” style architecture interconnected by covered breezeways and an expansive covered 1576 sq ft lanai. The center pod includes the open-concept gourmet kitchen, dining, and living areas — all flowing seamlessly to the outside lanai. Plus a versatile room ideal for an office, gym, theater room, or guest suite. The master suite is elegantly tucked into its own wing, offering sweeping ocean and mountain views The luxurious spa-style bathroom has a vibroacoustic therapy deep soaking spa tub, and just outside is a luxurious tropical shower. The bathroom is a generous open area featuring a large walk in closet, perfectly situated near the laundry room. The guest wing features two generous guest suites, each with expansive walk-in closets, and a well-appointed spacious bathroom. The guest wing provides comfort and privacy, with open lanai views to the ocean and the pool. Designed for effortless living, the home features 50+ smart lightbulbs and Alexa hubs, giving you full voice-activated control of the lighting in every room. Step outside to your own private oasis, featuring a heated salt-water lap pool with motorized cover, a jetted spa, and a bubbling fountain—perfect for relaxation or entertaining. The fully fenced grounds showcase lush Zoysia lawns, a raised-bed garden, mature tropical fruit trees, and prolific apple bananas, offering the delight of fresh-picked fruit anytime. A quarter-acre of pasture with two charming resident goats, this property captures the essence of country living. Enjoy prime potential for a 1,500 sq. ft. second dwelling, or envision an AG barn with a second story to create expansive, flexible living or storage space. Practical amenities include a workshop/garage, storage space, a grid-tied solar PV system with Tesla battery backup, and a Solar-plus-storage setup for energy efficiency. With its carefully curated finishes, open layout, and thoughtful integration of indoor-outdoor living, this North Shore Maui hideaway captures timeless elegance, modern sustainability, and private island charm. Don't miss these Stunning Triple Blue Views! Drop in and experience your special piece of paradise.

10 Leleaka Pl, Haiku

Listing courtesy of Century 21 Island Homes.

$3,333,000

7 Beds ⋅ 5 Baths ⋅ 409514 MLS ⋅ Fee Simple Tenure

Set on 2 acres of lush, tropical grounds, this is a gorgeous private, ocean view Haiku estate that offers a rare combination of space, flexibility, and luxury. The main home has warm wood finishes, exposed beam ceilings, and an open layout that brings in natural light all around. The craftsmanship throughout is immediately felt—from the solid wood flooring underfoot to the custom details that give the home both substance and warmth. In addition to the main residence, there are four well-integrated living spaces, including an attached 2/1 and 3/1, as well as a detached ohana and a separate studio space. Whether for extended family, guests, or simply creating a more expansive way of living, the layout allows for a level of versatility that’s increasingly hard to find. The resort-style pool area captures ocean views and is designed for relaxation and entertaining. Entry to the home is marked by a serene garden setting, complete with a koi pond, water features, and a footbridge that sets a calm, intentional tone as you arrive. This property balances multiple living spaces while still feeling like a single, cohesive estate. It’s well-suited for those looking for a private retreat, a multi-generational setup, or a Maui home that offers more than just one way to live. Located with easy access to the North Shore and Paia, this is a property that offers both privacy and convenience in equal measure.

1073 Nanihoku Pl, Haiku

Listing courtesy of eXp Realty.

$1,425,000

3 Beds ⋅ 3 Baths ⋅ 409390 MLS ⋅ Fee Simple Tenure

Tucked away on 1.47 lush agricultural acres in Haiku, this private property offers a rare blend of flexibility, privacy, and island charm. Public records reflect a 2-bedroom, 2-bath home, while the adaptable layout allows for multiple living options, including a potential attached studio or separate-entry unit—ideal for extended family, guests, or rental income. The home features a spacious, open feel with seamless indoor-outdoor living. Mature landscaping includes a variety of fruit trees—lime, Hawaiian lemon, coconut, banana, and sugar cane—along with puakenikeni, heliconia, and gardenia and other tropical flowers. A peaceful bamboo grove adds to the sense of serenity, tucked within the uncultivated portion of the acreage. Additional highlights include a detached structure with an Endless Pool spa and storage, extra outbuildings, and two fenced areas suited for gardening, pets, or agriculture. Set back from Holokai Road behind a gated entry, the property offers exceptional privacy in a peaceful Haiku setting. Within a 15 minute drive, are stores, schools, post office and beaches. Some images include virtual staging.

145 S Holokai Rd, Haiku

Listing courtesy of REMAX Hawaii Maui.

$3,999,000

5 Beds ⋅ 6 Baths ⋅ 409285 MLS ⋅ Fee Simple Tenure

Situated on two privately fenced and gated acres in Haiku, Holokai Hale is a North Shore estate designed for indoor-outdoor living. More than 1,600 square feet of covered space includes lanais, walkways, and multiple areas to relax. Plumeria and puakenikeni line the grounds, with partial ocean views through the canopy. The home offers five bedrooms, six bathrooms, and over 5,000 square feet. The main residence centers on a chef’s kitchen with a large island, butler’s pantry, and direct access to covered lanais for dining and entertaining. Interior and exterior spaces connect seamlessly. The grounds include a saline pool and spa, sauna, cold plunge, and established landscaping with raised garden beds, papaya trees, banana and ginger groves, citrus, lei flowers, and a mature soursop tree. You will find vaulted ceilings and Brazilian Tiger wood floors and each bedroom includes an en-suite bathroom with the primary bedrooms Italian White Carrara Marble bathroom and extra large dressing suite. A separate guest suite provides privacy for extended stays. Additional structures include a detached workshop, an air-conditioned studio with its own sink, and a bonus room above the garage which also has a dumbwaiter. The property is supported by a 52-panel photovoltaic system, solar hot water, split air conditioning, and a whole-home backup generator. Holokai Hale is a flexible property suited for a primary residence, extended family living, or a private retreat.

65 N Holokai Rd, Haiku

Listing courtesy of Keller Williams Realty Maui-Ki.

$2,775,000

5 Beds ⋅ 4 Baths ⋅ 408952 MLS ⋅ Fee Simple Tenure

More fun per square foot than any property on Maui. Wake up every day to your own private, resort-style oasis featuring a 25'x40' free-form saline pool with a jacuzzi, water slide, jumping rocks, sauna, outdoor shower, stone fire pit, and tiki bar. When you’re not swimming, jumping, sliding, sweating or otherwise enjoying this tropical 2-acre estate you’ll be embraced by a 5-bedroom, 4-bathroom home with an expansive open floorplan and a warm redwood interior that seamlessly blends indoor and outdoor living. The chef's kitchen is equipped with top-of-the-line appliances, including a Dacor cooktop, GE double oven, Sub-Zero refrigerator and a wine cooler, complemented by custom monkey pod and bamboo cabinets. Luxurious features exist like a stone fireplace, a multi-purpose loft, and a primary suite with a large soaking tub and walk-in shower. The wraparound lanai showcases tropical views and inviting outdoor living spaces. There are impeccably landscaped grounds with fruit trees, garden beds and various additional structures, plus a 12kw net metered solar system for sustainable energy efficiency. Indulge in the ultimate Maui lifestyle with a property that transcends the ordinary. Words and images fall short in capturing the magic of this residence which must be seen to be enjoyed. Discover the unparalleled charm of this exceptional Maui estate.

1780 Kauhikoa Rd, Haiku

Listing courtesy of The Maui Real Estate Team Inc.

$3,495,000

5 Beds ⋅ 3 Baths ⋅ 408773 MLS ⋅ Fee Simple Tenure

Set across sixteen acres of fully fenced acreage, this Haiku estate is a world unto itself. Private, expansive, and rich with possibility. Thoughtfully positioned structures create a harmonious compound designed for inspired living, hosting, and creativity. Whether envisioned as an exclusive mountain residence, an artist’s enclave, or a destination wellness retreat, the setting effortlessly supports a life well-lived. At the heart of the property, the main home captures the essence of refined rural living. An impressive primary suite is wrapped in glass windows and doors, inviting natural light and lush views from nearly every angle. A warm fireplace lounge in the living area sets the tone for intimate evenings, while a concealed projection screen transforms the space into a private cinema. The screened lanai area offers flexibility for gatherings or hosting events of any kind. Throughout the grounds, there are additional dwellings and versatile spaces, including a two-room cottage currently utilized as an office, an upper guest cottage with its own outdoor shower house, and a two-story building tucked privately toward the rear of the acreage. Each structure enhances the estate’s ability to accommodate guests or creative pursuits. The outdoor experience is equally compelling. Pass by the courtyard area and enjoy the sounds of the cascading waterfall and koi fish pond, and head out to meandering trails that wind through the landscape. A commercial-grade kitchen with an adjacent screened-in gathering space, along with dedicated men’s and women’s bathhouses, reflects the property’s history as a curated retreat destination. Leisure and restoration take center stage with a resort-style pool complete with a water slide, waterfall, an accompanying pool house, and a tranquil massage pavilion. This is more than acreage; it is a legacy estate with the capacity to evolve alongside your vision, all within a setting that feels worlds away.

1055 Kaupakalua Rd, Haiku

Listing courtesy of Hawaii Life (W).

$7,950,000

3 Beds ⋅ 2 Baths ⋅ 408161 MLS ⋅ Fee Simple Tenure

Seller is now offering FULL ownership in this truly irreplaceable North Shore Maui oasis. Set amid panoramic ocean, coastline, and waterfall views, this sanctuary offers rare natural resources and privacy. Enter through hand-crafted 24-foot custom gates into a double-fenced private estate featuring 6 permitted structures thoughtfully designed with a blend of Japanese, Hawaiian, and Balinese architectural influences. Improvements include a dedicated ag center, office/garage, infrared sauna, custom loft, and multiple living spaces that harmonize seamlessly with the surrounding landscape. A stone walking path encircles the property, guiding you through a stunning rainbow eucalyptus forest, paperbark tree grove, and a variety of producing trees including cherry, papaya, banana and more. A wrap-around driveway with parking for 20+ vehicles makes the estate ideal for hosting gatherings and entertaining family/friends. This self-sustaining retreat features a 280-foot private well with county water rights, nutrient-rich soil ideal for agriculture, and owned solar with commercial-grade infrastructure. Enjoy ocean and waterfall access from the property! An opportunity to fully own one of Maui’s most inspiring and unique estates—Don’t miss out!!!

180 Door Of Faith Rd, Haiku

Listing courtesy of eXp Realty.

$12,900,000

4 Beds ⋅ 4 Baths ⋅ 406606 MLS ⋅ Fee Simple Tenure

Perched on a sweeping green slope with panoramic ocean and mountain views, this award-winning Haiku retreat blends modern architecture with the serene elegance of a high-end sanctuary. Designed by renowned firm SEE Architecture, the home draws inspiration from iconic museums like the Getty and Venice Guggenheim, mid-century modern design, and the quiet refinement of luxury retreat spaces. Behind a minimalist facade, the experience unfolds—floor-to-ceiling glass reveals unobstructed vistas, blurring the line between indoors and out. Natural materials—including vein-cut silver travertine, western red cedar, and walnut crafted by local artisans—anchor the home to its surroundings. The structure itself is a precision steel BONE system, designed for longevity and environmental harmony. Inside, the interiors are curated with intention: Florim Italian porcelain tile throughout, custom millwork by Henrybuilt in the kitchen, baths, and beyond, handmade Heath Ceramics tile details, bronzed Honduran mahogany pivot door entry, Forbes & Lorax light switches, Phillip Jeffries woven wall coverings, and Waterworks fixtures and finishes. The open-plan layout flows effortlessly from artful entry to the main living spaces, with every room oriented toward the lush, private acreage and distant blue horizon. Beyond the glass, the landscape includes sculptural elements like Chinese scholar’s rocks, a sleek modern swimming pool, and rolling pastures where horses roam. A separate guest cottage provides additional space for visitors, work, or creative pursuits, all while maintaining the retreat’s sense of privacy. The arrival experience is equally compelling—lush, mature landscaping lines the private drive, a verdant gateway cultivated over the past 20 years with care and intention. Several acres of established orchard also grace the property, producing a bounty of citrus, avocado, mango, banana, starfruit, and more—a testament to the land’s abundance and stewardship. A thoughtfully built 1,152 sq ft barn sits tucked near a private eucalyptus forest—an elegant, utilitarian complement offering exceptional potential for future use. This is more than a residence—it’s a living gallery of design, detail, and tranquility.

1642 W Kuiaha Rd, Haiku

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

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Based on information from the Multiple Listing Service of Hicentral MLS, Ltd. Listings last updated on . Information is deemed reliable but not guaranteed. Copyright: 2026 by HiCentral MLS, Ltd. IDX information is provided exclusively for consumers' personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.