Wailea/Makena Homes with Across Street from Ocean Waterfront

Wailea/Makena Homes with Across Street from Ocean Waterfront

Welcome to Wailea and Makena, two of Maui's most enchanting coastal gems, where the sun kisses the ocean and the spirit of Aloha thrives. Nestled in the heart of Kihei, this picturesque district boasts some of the most stunning oceanfront properties in Hawaii, making it a dream destination for homebuyers and vacationers alike.

Wailea is renowned for its luxurious resorts, world-class golf courses, and pristine beaches, offering a laid-back lifestyle that perfectly complements the island's natural beauty. With its gentle ocean breezes and breathtaking sunsets, living here means waking up to the soothing sounds of the waves lapping against the shore. Just a stone's throw away, Makena enchants with its rugged coastline, hidden coves, and the famous Big Beach, where you can bask in the sun or enjoy exhilarating water sports.

Imagine stepping out of your home and being greeted by panoramic views of the sparkling Pacific Ocean, with direct access to the sandy shoreline right across the street. These oceanfront properties provide a unique opportunity to experience island living at its finest, where every day feels like a vacation. Whether you’re sipping your morning coffee while watching the sunrise or hosting sunset gatherings with friends and family, the magic of Wailea and Makena is truly unparalleled.

With a vibrant community, upscale dining, and a plethora of outdoor activities, this district is perfect for those seeking both tranquility and adventure. Discover your slice of paradise in Wailea/Makena, where the ocean is your backyard and the spirit of Maui is your everyday companion.

Newest Wailea/Makena Homes with Across Street from Ocean Waterfront

$3,295,000
410110 MLS ⋅ Fee Simple Tenure
Ready to build your Makena, Maui Dream Home? Papa'anui, across from Makena Landing, is incomparable in its unique location. You will enjoy south facing Ocean, pristine Makena coastline, Kaho’olawe & Molokini Crater Views. This idyllic location affords spectacular sunsets with a beautiful sandy beach & majestic ocean waters just steps from your front door. Makena is just south of Wailea and is revered as a pristine, less-developed, magnificent coastal area. This World Class Makena Resort area is consciously & conservatively being developed adjacently by Discovery Land Company, an international developer of prime luxury, low density, membership communities. This property is easily accessible, approximately 5 minutes or less, to world class golf, dining, tennis, hiking, kayaking, paddle-boarding, horseback riding & diving. Makena offers a lifestyle that is quintessentially natural Maui. The Wailea Resort & the elegant Shops at Wailea are a very short drive. The Papaanui CC&R’s, plot plan, topo map & survey, along with a custom home rendering & elevations, are available upon request. There is a 3/4 inch County Water meter installed on the property & underground electrical infrastructure. * Included in the photos is an architectural rendering/concept by Maui Architectural Group envisioning a fabulous home design. Come watch the whales breach, frolic amongst the turtles & enjoy your 'Peace of Paradise'.

5159 Makena Rd, Kihei

Listing courtesy of Maui Real Estate Advisors LLC.

$2,749,000
2 Beds ⋅ 3 Baths ⋅ 409826 MLS ⋅ Fee Simple Tenure ⋅ Na Hale O Makena BLDG.
Welcome to Na Hale O Makena, one of South Maui’s most private and low-density luxury communities. This beautifully appointed 2-bedroom, 2.5-bath residence offers the ease and comfort of desirable ground-level living with no stairs/elevators to enter, creating effortless access throughout the home and lanai. Tucked within lush tropical landscaping, the property enjoys an exceptional sense of privacy and tranquility in one of Makena’s most sought-after settings. Freshly updated with a newly painted interior, new carpeting, led lighting and more, this spacious floor plan is designed for relaxed island living, featuring seamless indoor-outdoor flow and peek-a-boo ocean/molokini views that add to the home’s peaceful ambiance. Thoughtfully designed with comfort and convenience in mind, this residence lives more like a private home while still offering the benefits of luxury condominium ownership. Residents of Na Hale O Makena enjoy a gated, low-density community atmosphere along with resort-style amenities including a pool, spa, fitness center, and covered pavilion, all just moments from Makena’s pristine beaches, golf, dining, and Wailea conveniences. Whether you are seeking a full-time residence or an island retreat, this exceptional property captures the privacy, comfort, and understated luxury that define the Makena lifestyle. Schedule your private showing today!

4955 Makena Rd Unit F102, Kihei

Listing courtesy of Coldwell Banker Island Prop(S).

$26,500,000
6 Beds ⋅ 6 Baths ⋅ 409734 MLS ⋅ Fee Simple Tenure
THE ULTIMATE MAUI DREAM . .The most sophisticated are no longer asking where to live . .They are asking, “Where can we breathe?” Welcome to The Makena Generational Oceanside Retreat offering resort-style living with smart-home technology, unobstructed ocean & sunset views, Haleakala sunrise views situated on a professionally landscaped one-acre gated and walled tropical estate.The fully operational compound is ready for occupancy offering a vast combination of energy efficiency, self-sufficiency and refined comfort featuring the largest residential Tesla Solar Roof in the US installed in 2024. A unique opportunity to own a private Maui sanctuary of this stature where luxury, wellness and sustainability coexist in harmony. The indoor-outdoor lifestyle is designed for multigenerational living, executive retreats and legacy ownership. In a world moving faster than ever, it is intentionally crafted for life to slow down. Extensively upgraded under the current owner with substantial infrastructure, aesthetic and technology enhancements, the property is now offered well below current replacement cost. The Makena community remains one of Maui’s most coveted luxury destinations. The current property manager creates effortless luxury living with lock-and-leave convenience. The luxurious amenities are endless. The privately separated interior living areas offer exceptional craftsmanship, premium wood finishes, floor-to-ceiling bifold glass doors, elevator, gourmet kitchen, exercise area, massage room, sauna, and steam shower. The dramatic custom water features include a puka lava entry waterfall with pond and interior floor-to-ceiling water feature at the base of the floating staircase. The additional luxury oceanside pool home with its oversized heated pool includes its own gourmet kitchen, Italian brick pizza oven and rear projection entertainment system. Combined with many additional features, the estate offers a total of 8b-8b comfortably accommodating up to 16 guests. Parking is a breeze with a 4+car garage and generous additional parking areas.

7505 Makena Rd, Kihei

Listing courtesy of Compass-W.

$3,500,000
409689 MLS ⋅ Fee Simple Tenure
A rare and extraordinary opportunity in coveted Makena awaits. Just steps from world famous Makena Beach (Big Beach). This exceptional vacant lot spans approximately 28,706 sq. ft. (0.658 acres) and offers the perfect canvas to create your Maui Estate. Nestled within an exclusive gated subdivision of only four properties, this prime homesite combines privacy, tranquility, and the natural beauty that defines South Maui living. A ¾-inch water meter is already installed, and underground utilities are brought directly to the site for added convenience. Enjoy the soothing sounds of the ocean along with beautiful glimpses of the sparkling blue Pacific Ocean. Ideally located near championship golf courses, upscale shopping and dining, world class Wailea resorts, luxury spas, and pristine beaches, this property offers the very best of the Makena lifestyle. Truly one of Maui’s most special offerings. This is an exceptional opportunity to build in one of Hawaii’s most sought after coastal communities.

Makena Rd, Kihei

Listing courtesy of Hawaii Life (W).

$9,950,000
409403 MLS ⋅ Fee Simple Tenure
17 Maluaka within the prestigious, gated Maluaka enclave represents a rare and compelling opportunity to create a legacy estate in one of Makena’s most revered coastal neighborhoods. Encompassing approximately three-quarters of an acre, this exceptional property is ideally perched to capture sweeping ocean view corridors, offering a breathtaking backdrop for a world-class architectural masterpiece. As the largest lot in Maluaka, it offers a rare combination of scale, privacy, and design potential seldom found in Makena. Defined by privacy and exclusivity, Maluaka offers a serene, low-density setting where luxury and tranquility coexist. Behind the gates, a sense of seclusion prevails—yet it is just moments away from championship golf, unspoiled beaches, and the finest dining and shopping experiences of South Maui. Here, the rhythm of island living is elevated, where every sunset, ocean breeze, and whale breach become part of everyday life. This is more than a vacant lot in an exclusive neighborhood, it is an invitation to design and build a residence that reflects the very best of Maui’s luxury lifestyle in an address defined by rarity, privacy, and distinction. This is a residential CPR listing, please contact your favorite Realtor for more details.

17 Maluaka Pl Unit Unit 5, Kihei

Listing courtesy of Island Sotheby's Int'l Rlty(W).

$9,500,000
409319 MLS ⋅ Fee Simple Tenure
Set within one of Makena’s most coveted enclaves, this exceptional 3.349-acre homesite captures the essence of refined island living. 4520 Makena Alanui commands sweeping panoramic views of Makena’s shimmering coastline and the vibrant turquoise waters extending to Molokini, Kahoolawe, Lanai and the majestic West Maui Mountains. A rare offering, this expansive parcel presents the opportunity to create a legacy estate—an architectural masterpiece designed to embrace Maui’s natural beauty and indoor-outdoor lifestyle. Ultimate privacy and serenity define the setting, while Wailea’s world-class resorts, championship golf, fine dining, and luxury shopping remain just moments away. From sunrise over Haleakala to unforgettable sunsets melting into the Pacific, every day is framed by extraordinary beauty at this prime vacant lot. Inquire with your favorite Realtor to experience this remarkable property.

4520 Makena Alanui Dr, Kihei

Listing courtesy of Island Sotheby's Int'l Rlty(W).

$18,900,000
4 Beds ⋅ 5 Baths ⋅ 409020 MLS ⋅ Fee Simple Tenure
Experience the best of South Maui living in this exclusive Makena Sunset residence, ideally located directly across from Maluaka Beach, Makena, Maui. Enter through a private gated entry to one of only four homes in this intimate and highly sought-after neighborhood. Enjoy the ultimate island lifestyle with the beach just steps away for snorkeling, swimming, and sunsets. This spacious home features 4 bedrooms and 4 full and 2 half baths, designed for comfortable indoor-outdoor living. The large open kitchen flows seamlessly into the main living area, perfect for entertaining family and friends. Outside, a private pool and spa create a relaxing retreat surrounded by the beauty and tranquility of Makena. Rarely available and exceptionally located, this property offers privacy, exclusivity, and effortless access to one of Maui’s most beloved beaches. This offering affords the new owner to apply for membership to Makena Golf and Beach Club. This offering is a standalone home within Makena Sunset, a Residential Condominium.

5417 Makena Rd Unit 2, Kihei

Listing courtesy of Discovery Makena Realty LLC.

$4,650,000
3 Beds ⋅ 4 Baths ⋅ 408839 MLS ⋅ Fee Simple Tenure ⋅ Hoolei BLDG.
E Komo Mai and welcome to Ho'olei 21-4, an elegant 3 bed, 3.5 bath townhome located in the heart of Wailea, Maui. This Hotel Zoned property boasts wonderful ocean views and is offered tastefully furnished, totally turnkey, and is active and successful in the Grand Wailea's exclusive vacation rental program. The Plumeria floor plan enjoys the widest lanai and forward most position of the building, enhancing privacy and extending the living area. This villa has new upgraded flooring in the bedrooms, a chef's kitchen with Wolf and Sub Zero appliances, a built in BBQ and fridge on the lanai, attached garage, private elevator, and so much more. Pocketing Fleetwood glass sliders blend the indoors with the outdoors, making a perfect space for entertaining your family and guests. The Ho'olei property offers a resort style pool and spas, with a state of the art workout facility and saunas. Ho'olei is gated with 24hr security and lush landscaping that gives you a sense of place here in Hawai'i. Owners are eligible for the Kulana Club with the Grand Wailea, allowing them rental management, shuttle service, on-site front desk and concierge, as well as a myriad of discounts and perks. The Wailea Resort offers some of the finest dining, shopping, golf, tennis, beaches, sunny days and views in the world!

21 Kiloa St Unit O-4, Kihei

Listing courtesy of Hawaii Life (W).

$3,500,000
408307 MLS ⋅ Fee Simple Tenure
Set on approximately ±0.5 acres (20,573 sq ft), this exceptional gated property offers unobstructed ocean views in one of South Maui’s most coveted locations—directly across from Makena Landing with immediate beach and ocean access. The elevated parcel provides an ideal setting for a private coastal retreat, capturing sweeping sunset views, cooling trade winds, and the soothing presence of the Pacific. With ample space to create a custom residence and resort-style outdoor living, this rare offering combines privacy, natural beauty, and an iconic Makena lifestyle—just moments from some of Maui’s most celebrated beaches and outdoor experiences. Purchasers also have the unique opportunity to apply for membership to Makena Golf and Beach Club, enhancing their lifestyle with exclusive amenities and privileges. Disclaimer: This is a lot only sale. Renderings are for illustrative purposes only and represent conceptual imagery of a potential future residence. No plans or approvals are included in the purchase. Buyer to independently verify all information and obtain any necessary permits and approvals.

5171 Makena Rd Unit Lot 7, Kihei

Listing courtesy of Discovery Makena Realty LLC.

$4,999,999
3 Beds ⋅ 4 Baths ⋅ 408222 MLS ⋅ Fee Simple Tenure ⋅ Hoolei BLDG.
Discover luxury resort living in this exceptional ocean-view Villa located within the prestigious gated community of Ho'olei in Wailea. It is ideally positioned near world-class resorts, fine dining, luxury shopping, championship golf courses, and Maui's best beaches. The Villa features 3 bedrooms and 3.5 bathrooms, in a two-story townhome-style, encompassing 2,426 square feet. There is an additional 596 square feet of covered lanais across two levels. Each bedroom includes a private ensuite bath, offering comfort and privacy for owners and guests alike. Thoughtful design elements include a private elevator, an attached garage, a covered carport, and an outdoor storage closet. Floor-to-ceiling sliding glass doors and retractable screens open almost 30 feet onto the expansive lanai, embracing Maui's indoor/outdoor lifestyle. The lanai is ideal for entertaining and is equipped with a Wolf 36" grill, a Sub-Zero under-counter refrigerator, and custom cabinets. The Villa features polished travertine floors, recessed lighting, high tray ceilings, surround sound, a security system, and a 2-zone central air conditioning system. The Chef's kitchen includes premium appliances by Sub-Zero, Wolf, Thermador, and Bosch. A touch of elegance is added with the Snaidero Italian custom cabinetry. You can enjoy ocean views from high above the resort pool. Ho'olei's amenities include a lagoon-style pool with cascading waterfalls and grottos, a sandy beach entry, two hot tubs, a massage cabana, an outdoor kitchen with covered pavilion, and a fully equipped, air-conditioned fitness center with sauna, locker rooms, and showers. Offered fully furnished, the Villa is truly turn-key & has been meticulously maintained. The property is hotel-zoned, allowing use as a short-term vacation rental, private residence, or a combination of both. Successfully operated as a vacation rental since 2007, the Villa has received over 150 five-star reviews. The owner is willing to continue marketing the property or assist with a smooth transition to new management. This remarkable Ho'olei Villa presents a rare opportunity to own a luxury, hotel-zoned home in paradise.

81 Makakehau St Unit Apt H-2, Kihei

Listing courtesy of Coldwell Banker Island Prop(S).

$2,600,000
2 Beds ⋅ 3 Baths ⋅ 407743 MLS ⋅ Fee Simple Tenure ⋅ Na Hale O Makena BLDG.
Escape to your own serene tropical sanctuary with gorgeous ocean views in this exceptional Na Hale O Makena C302 residence. Thoughtfully crafted and tastefully upgraded, this home features two spacious bedrooms with ensuite baths, a powder room, in-unit laundry, and a large storage closet perfect for pantry use. The thoughtful floor plan is designed for comfortable living. The open kitchen is a true highlight, offering granite countertops, gas cooking, and high-end stainless steel appliances, including a beverage cooler. It opens seamlessly to the generous living area and out to the lanai, where you’ll be greeted by breathtaking ocean vistas. With an outdoor grill and cooler, it’s an ideal setting for relaxed island entertaining and endless memorable sunsets. Tucked at the end of the road, Building C enjoys a quiet, private setting. Added conveniences include an elevator, covered carport parking, and extra storage, all contributing to a lifestyle of ease and tranquility. As part of a private, low-density community of just 40 residences with an onsite resident manager, you’ll enjoy over six acres of beautifully landscaped tropical grounds. The impressive clubhouse offers a saline pool, spa, and fitness room, creating a resort-like experience without leaving home. And with pristine beaches, dining, shopping, and premier golf courses nearby, you’re perfectly positioned to enjoy everything Maui has to offer. Experience refined Hawaiian living in this unforgettable Makena retreat.

4955 Makena Rd Unit C302, Kihei

Listing courtesy of Coldwell Banker Island Prop(P).

$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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