Wailea/Makena Homes with Pool

Welcome to Wailea and Makena, two of the most coveted neighborhoods in Maui, Hawaii, where luxury meets paradise. Nestled along the southern coast of the island, these stunning communities are known for their breathtaking ocean views, pristine beaches, and lush tropical landscapes. Wailea and Makena offer an idyllic lifestyle that combines relaxation with adventure, making it the perfect destination for families, retirees, and anyone looking to embrace the beauty of island living.

The neighborhoods are characterized by their upscale homes, many of which feature private pools, allowing residents to enjoy the ultimate in comfort and leisure. Imagine lounging by your own pool, surrounded by swaying palm trees and the gentle sound of waves lapping at the shore. Whether you prefer a modern architectural masterpiece or a charming Hawaiian-style bungalow, Wailea and Makena boast a diverse array of properties to suit every taste.

Beyond the stunning homes, residents can take advantage of the world-class amenities that these neighborhoods offer. From championship golf courses and luxury resorts to boutique shopping and exquisite dining, there's always something to explore. The nearby beaches, such as Makena Beach and Wailea Beach, are perfect for sunbathing, snorkeling, or simply taking in the spectacular sunsets that paint the sky in vibrant hues.

With a strong sense of community and a laid-back lifestyle, Wailea and Makena invite you to experience the best of island living. Come and discover your dream home in this tropical paradise, where every day feels like a vacation.

Newest Wailea/Makena Homes with Pool

$34,000,000

4 Beds ⋅ 6 Baths ⋅ 410368 MLS ⋅ Fee Simple Tenure

Discover a rare chance to create your legacy in Maluaka Estates, an intimate, private gated enclave of only 13 custom estates in the heart of Makena. Just moments from the golden sands of Maluaka Beach and adjacent to the world-class amenities of the Makena Golf & Beach Club, this exclusive homesite offers an unparalleled blend of luxury, privacy, and island living. More than a homesite, this is a thoughtfully curated pathway to your dream island residence. The property includes membership application rights to the club, opening the door to an extraordinary lifestyle defined by championship golf, ocean adventures, wellness experiences, and exceptional dining. Designed for ease and convenience, the property is part of a seller-organized construction program for a fully permitted, world-class luxury home. Architectural plans have already been submitted to Maui County for permit approval, allowing you to bypass years of planning and begin bringing your vision to life with confidence. Imagine mornings spent along Makena’s stunning coastline, afternoons enjoying club amenities, and evenings relaxing in a custom estate designed to embrace the beauty of island living. This is a unique opportunity to secure a place in one of South Maui’s most coveted communities and enjoy the very best of the Makena lifestyle. Disclaimer: The offering price of the lot & house package is $34,000,000. The lot sale will occur first under a separate purchase agreement. Following the successful closing of the lot, the buyer and builder are expected to enter into a separate construction agreement for the proposed residence. The home depicted in the listing is not currently under construction. All photographs, renderings, floor plans, elevations, and other visual materials are artist's conceptual renderings only and are provided solely to illustrate a potential home design. Final architectural plans, specifications, dimensions, materials, finishes, features, pricing, and other design elements are subject to change. A due diligence/design review period will be provided following the lot purchase to review the proposed home plans with the buyer. During this period, the buyer may request revisions to the design, specifications, and finishes, subject to applicable approvals, feasibility, and agreement between the parties, before construction begins. Construction will not commence until final plans, specifications, permits, budgets, and contractual terms have been approved and executed. Estimated construction timelines have not yet been finalized and will be determined after completion of the design process, permitting, and execution of the construction agreement. Any references to square footage, features, amenities, pricing, or completion dates are preliminary and subject to modification. Buyers should independently verify all information and are encouraged to consult with the seller, builder, architect, and their own advisors regarding all aspects of the proposed project. Listing information is deemed reliable but is not guaranteed. This is Residential Condo (CPR) - This is a Residential Condo Property, and this unit approved for a main house.

18 Maluaka Pl Unit Unit 1, Kihei

Listing courtesy of Discovery Makena Realty LLC.

$29,900,000

5 Beds ⋅ 6 Baths ⋅ 407766 MLS ⋅ Fee Simple Tenure

Perched on one of Makena’s most coveted cliffside locations, this contemporary direct-oceanfront estate is perfectly situated along an intimate cove, offering breathtaking, unobstructed Pacific views from nearly every room. Set on over 22,190 sq. ft. of land, this two-story, five-bedroom, five-and-a-half–bath residence is a masterpiece of luxury and Hawaii’s signature indoor–outdoor living. Designed by world-renowned architect Guy Dreier, the home is a livable work of art, featuring soaring ceilings, dramatic architectural lines, and an innovative floor plan. Step through the entryway into an entertainer’s paradise. The expansive great room flows effortlessly through large pocket doors to the oceanfront deck, where a stunning infinity-edge pool appears to spill into the sea—ideal for sunset gatherings or peaceful mornings with coffee in hand. Multiple living and dining areas, along with a dedicated service area, create an unparalleled setting for both intimate dinners and large-scale celebrations. The exquisite primary suite and three guest suites each offer private ocean-view lanais, providing serene retreats with panoramic vistas. A beautifully appointed attached Ohana unit adds exceptional flexibility for guests, extended family, or a caretaker. Move-in ready and designed for effortless hospitality, this is more than a home—it’s a true Makena masterpiece blending modern coastal luxury with the timeless beauty of Maui’s south shore.

5050 Makena Rd, Kihei

Listing courtesy of Discovery Makena Realty LLC.

$2,225,000

3 Beds ⋅ 3 Baths ⋅ 409250 MLS ⋅ Fee Simple Tenure

Set within the prestigious Wailea Pualani Estates, this 3-bedroom, 2.5-bath residence with an additional office/media room offers refined island living with a seamless indoor-outdoor flow. The private backyard is designed for entertaining, featuring a saline heated pool with waterfall features, surrounded by lush, mature landscaping. The ocean-view primary suite includes a private lanai, creating a peaceful space to take in Maui’s sunsets. Recent upgrades include a new standing seam metal roof, owned photovoltaic system with two Tesla backup batteries, new split A/C units, and a freshly painted interior. Ideally located just minutes from Wailea’s world-class beaches, golf, dining, and resorts, this is an exceptional opportunity in one of South Maui’s most sought-after communities.

3386 E Lani Ikena Way, Kihei

Listing courtesy of Compass-W.

$4,095,000

4 Beds ⋅ 5 Baths ⋅ 408523 MLS ⋅ Fee Simple Tenure

The newly completed Wailea estate blends contemporary design with Maui’s natural beauty. Ocean-view living with seamless indoor-outdoor flow, abundant natural light, and locally inspired textures. Open-concept great room features panoramic ocean views, floor-to-ceiling glass, hardwood floors, and natural stone. Chef’s kitchen with waterfall stone island, premium appliances, and custom cabinetry. Luxurious bedroom suites offer spa-style baths, private lanais, and ocean or garden views. Resort-style outdoor living includes a lap pool, spa, Baja shelf, and tropical landscaping. Sustainable features include solar, smart home automation, and energy-efficient systems. Prime Wailea location near world-class beaches, golf, dining, and luxury resorts. One of the listing agents is the seller.

3378 E Lani Ikena Way, Kihei

Listing courtesy of Coldwell Banker Island Prop-Ku.

$11,998,000

4 Beds ⋅ 5 Baths ⋅ 406282 MLS ⋅ Fee Simple Tenure

Perched atop the exclusive and private enclave of The Ridge at Wailea, this extraordinary Guy Dreier-designed residence is a rare expression of contemporary architecture where architecture, light, and nature exist in perfect harmony. Masterfully built by Trend Builders, this remarkable residence is more than a home—it is a livable sculpture. Every curve, angle, and architectural detail was thoughtfully conceived to frame breathtaking ocean vistas stretching from Molokini across the sparkling Pacific to the majestic West Maui Mountains. A dramatic covered entry welcomes you through a striking black magma stone courtyard, where a sculptural steel and stone spiral staircase sets the tone for the extraordinary experience that follows. Beyond, soaring walls of glass dissolve the boundaries between indoors and out, filling the home with natural light while embracing Maui's celebrated indoor-outdoor lifestyle. As the sun moves across the sky, light becomes part of the architecture, transforming the home's sculptural forms into an ever-changing living work of art from morning through sunset. Offering over 5,000 square feet of thoughtfully designed living space, the residence features four bedrooms, four and one-half baths, expansive living and dining areas, a media room, elevator, spacious multi-car garage, and two private bedroom wings that provide exceptional comfort and privacy for family and guests alike. The primary south wing offers a serene retreat complete with a spa-inspired bath, indoor and outdoor showers, walk-in closet, private lanai with coastal views, adjacent office or guest suite, laundry room, and private elevator access. The north wing features an equally impressive primary suite with sweeping ocean views, a private poolside lanai, walk-in closet, indoor and outdoor shower, and convenient access to the home's exceptional entertaining spaces. At the heart of the residence, the chef's kitchen is designed for both everyday living and unforgettable gatherings, featuring a generous island, walk-in pantry, sunken conversation bar, Miele wine refrigeration, and premium appliances. Just beyond, expansive lanais surround the striking Avant-Garde pool and spa, built-in barbecue, inviting fire pit, and multiple outdoor living and dining areas designed to celebrate Maui's year-round climate. Refined finishes throughout—including soaring ceilings, dramatic quartzite slab surfaces, custom Poliform systems, and exceptional craftsmanship—create an atmosphere of understated sophistication. Every space has been carefully curated to maximize comfort, privacy, and the home's extraordinary connection to its natural surroundings. More than a residence, this is a home designed to be experienced—where inspired architecture, extraordinary light, and breathtaking ocean views become part of everyday life. Maui, It's a Lifestyle! It's Time to Make It a Part of Yours! Listing Broker has a recorded ownership interest in the property and is licensed in the State of Hawaii.

14 Halapa Pl, Kihei

Listing courtesy of Hawaii Life (W).

$23,000,000

4 Beds ⋅ 5 Baths ⋅ 402062 MLS ⋅ Fee Simple Tenure

Nestled along the prestigious Makena coastline, 7595 Makena Road represents the pinnacle of contemporary Hawaiian luxury living. This extraordinary residence stands as a masterpiece where architectural innovation meets paradise. Perched on an expansive and private one-acre lot, this four-bedroom haven commands breathtaking views of the mesmerizing Ahihi Bay, where emerald and turquoise waters dance in eternal harmony. Each morning brings nature's theater to your doorstep, with the gentle lapping of waves providing the perfect soundtrack to your day. The dwelling is comprised of a total of 6643sf: 4778sf of living space, 995sf of covered lanai space to enhance the indoor/outdoor living, and an oversize, three-car garage of 870sf. The home's thoughtful design seamlessly integrates indoor and outdoor living spaces, featuring: - Four luxurious en-suite bedrooms, each offering a private sanctuary - Open-concept baths with spacious showers and captivating ocean views - State-of-the-art smart home technology throughout - Private elevator ensuring effortless accessibility - Custom finishes that reflect both modern luxury and island charm As one of Makena's newest luxury estates, this residence offers more than just a home – it's an invitation to experience Maui's most coveted lifestyle. The property's privileged location provides the perfect vantage point for witnessing the island's legendary sunsets and seasonal whale watching. Built in 2022, this contemporary masterpiece represents the perfect blend of modern amenities and timeless island elegance. Every detail has been carefully curated to create an environment where luxury isn't just a feature – it's a way of life. This rare offering stands as a testament to sophisticated island living, where every detail has been thoughtfully designed to create an unparalleled living experience in one of Maui's most sought-after locations. Don't let this unparalleled Makena estate slip away – seize the opportunity to be the first owner of this exceptional estate.

7595 Makena Rd, Kihei

Listing courtesy of Compass-W.

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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.