Wailea and Makena

Since its development commenced in the 1970’s, Wailea has enthralled visitors and residents alike with its picture-perfect weather, championship-caliber golf courses, critically-acclaimed restaurants, world leading resorts, and famed beaches. As a master-planned community, the standard for care and quality is high, which shows in the extreme pride of ownership among properties throughout the resort and with strong leadership at the helm of the Wailea Community Association, the future is bright.
This content is currently unavailable. Please check back later or contact the site's support team for more information.

Set along Maui’s stunning southern coast, Wailea and Makena represent the pinnacle of luxury island living. From world-renowned beaches and championship golf courses to resort-style amenities woven seamlessly into breathtaking natural landscapes, this corner of South Maui offers an unmatched blend of relaxation, refinement, and cultural richness. Here, privacy and prestige meet everyday access to sun-soaked adventures, making it one of the most desirable destinations for discerning buyers and investors.

Take a closer look at Wailea and Makena and the available real estate with Kate Peterson, whose eight-generation family history on Maui and a two-generation realtor team, provides the deepest insight rooted in tradition and community. Her experience provides more than guidance in finding the right property; Kate Peterson offers a trusted connection to Maui’s exceptional lifestyle.

A Brief History of Wailea and Makena

Long before Wailea and Makena became synonymous with luxury living, these islands carried deep meaning for Native Hawaiians. Makena, translated as “abundance”, reflects the generosity of the land and sea that sustained generations. Fishing villages once lined the coast, while the fertile uplands supported taro cultivation, ranching, and family homesteads. The area’s cultural significance endures, with stories, legends, and place names that root the community in a legacy far older than its modern resorts.

As Maui grew, Wailea and Makena began a careful transformation. In the latter half of the 20th century, developers envisioned a resort community that could honor the land’s natural beauty while welcoming travelers and new residents from around the world. Wailea emerged as a thoughtfully planned enclave, with world-class hotels, golf courses, and residential neighborhoods designed to blend into the coastline rather than overwhelm it. South of Wailea, Makena retained a quieter, more expansive character, with stretches of untouched shoreline and fewer developments, creating a balance between resort polish and natural retreat.

Today, Wailea and Makena are destinations where cultural roots and modern luxury converge, places where the Hawaiian past is not forgotten but layered into the daily living experience. From the ancient trails that still cross the landscape to the preservation of open spaces and marine sanctuaries, the story of Wailea and Makena is one of continuity: a deep respect for the island’s origins paired with a vision for a refined, enduring future.

Real Estate in Wailea and Makena

The real estate landscape in Wailea and Makena is as varied as the coastline itself, offering different opportunities for different types of buyers. From elegant condominiums with resort-style amenities to expansive oceanfront estates designed for privacy and prestige, the properties here are defined by their connection to the island’s most spectacular surroundings.

For many, finding Wailea and Makena real estate is as much a lifestyle choice as it is a financial investment. Families are drawn to the sense of security and community within gated neighborhoods, professionals appreciate the balance of prestige and convenience, and retirees can enjoy the more relaxed pace of life with refined amenities. The area also holds strong appeal for send-home buyers and investors, who see Maui not just as a destination, but a long-term legacy.

In Wailea, gated communities such as Wailea Golf Estates, Maluhia at Wailea, and Wailea Highlands offer refined living amid manicured landscapes and sweeping ocean views. Many of these neighborhoods sit just steps from championship golf courses and world-class resorts, giving residents easy access to fine dining, spa retreats, and cultural events. For those after a more flexible lifestyle, Wailea homes for sale, like Ho’olei and Wailea Beach Villas, provide spacious residences paired with five-star service and amenities.

Further south, Makena offers a quieter alternative. Makena real estate emphasises larger parcels and custom-built estates, many with direct beach access and panoramic views across Molokini Crater and Kaho’olawe. This part of South Maui appeals to buyers who value privacy and space while still enjoying proximity to Wailea’s conveniences.

Every property here carries with it the essence of Maui: views that stretch for miles, architecture that blends seamlessly with the land, and an enduring sense of tranquility. With so many pluses, Wailea and Makena continue to be considered prime property in South Maui’s luxury real estate market.

Living in Wailea and Makena

Life in Wailea and Makena is defined by balance, blending resort-style luxury and the everyday comforts that make a community feel like home. From ease of transportation to quality schools and a lifestyle that reflects true island values, these South Maui enclaves are as livable as they are prestigious.

Getting Around

Wailea and Makena sit less than 30 minutes away from Kahului Airport, the island’s main hub, and both are easily reached via the Pi’ilani Highway. Within Wailea, thoughtfully designed resort zones make it easy to walk between beaches, restaurants, and shops, while scenic pathways like the Wailea Beach Path encourage residents to enjoy the coastline on foot. Golf carts are a common convenience in certain neighborhoods, further adding to the relaxed rhythm of daily life. Nearby towns such as Kihei and Makawao offer additional dining, shopping, and cultural experiences within a short drive.

Schools

Education is a key consideration for families exploring real estate in Maui, and South Maui offers a rich mix of choices. Nearby Kamali‘i Elementary in Kihei delivers strong public education in a nurturing environment. For private, college-preparatory excellence, Seabury Hall (Makawao) offers a rigorous academic experience with small classes and Blue Ribbon recognition. Kamehameha Schools – Maui Campus further enhances options by blending high academic standards with Native Hawaiian cultural values, making it a uniquely enriching choice.

For families looking for holistic, creativity-driven schooling, Haleakalā Waldorf School in Kula offers Waldorf-style education from preschool through high school, focused on individual development and critical thinking. Kīhei Charter School brings a modern twist with tuition-free, project-based K–12 learning centered on STEM and the arts.

The range of public and private schools ensures that homebuyers in Wailea and Makena can find an educational path that aligns with both the academic and lifestyle needs of their children.

Cost of Living

As two of Maui’s premium communities, Wailea and Makena command a higher cost of living. However, lower-density neighborhoods, resort-level upkeep, and 24-hour security services all contribute to the sense of ease and refinement enjoyed by the residents. The cost is simply viewed as an investment in the quality of life.

These communities balance sophistication with a genuine connection to Maui’s natural beauty, offering residents the rare quality of living in a place that is at the same time luxurious and rooted in nature. For such a place, many consider the cost of living worth the price.

Things to Do in Wailea

Outdoor Activities

Wailea is a playground for those who love the outdoors, with a coastline that offers something new every day. Wailea Beach is the community’s signature shoreline, a broad golden crescent consistently ranked among the world’s best. Families gather here for swimming and paddleboarding, while nearby Ulua Beach draws snorkelers eager to explore coral reefs teeming with sea life. The Wailea Beach Path weaves along the coast for nearly two miles, linking resorts, beaches, and parks with stunning ocean views. Golfers are spoiled with three championship courses at the Wailea Golf Club, each framed by palm trees, lava rock landscapes, and endless Pacific horizons.

Dining

Culinary experiences in Wailea are as refined as its real estate. Residents and visitors flock to Monkeypod Kitchen for locally inspired comfort food, while The Restaurant at Hotel Wailea creates elegant, multi-course dining with panoramic ocean vistas. Restaurants such as Humuhumunukunukuāpua‘a provide unforgettable evenings where fine dining meets Maui’s legendary sunsets. Hidden cafés and resort lounges round out the scene, offering quick bites and cocktails after a day on the water or golf course.

Shopping

The center of Wailea’s retail world is The Shops at Wailea, a collection of luxury boutiques, international fashion houses, fine jewelers, and art galleries. Here, browsing feels less like an errand and more like an indulgence, with everything from designer clothing to locally crafted treasures. Weekly markets and artisan fairs add variety, giving residents access to fresh produce, handmade goods, and island-inspired décor. Shopping in Wailea blends global luxury with local authenticity, ensuring every experience feels unique.

Art & Culture

Beyond its beaches and resorts, Wailea has a thriving cultural heartbeat. Seasonal art festivals bring galleries outdoors, showcasing works by local and international artists. Film screenings under the stars and live performances infuse the community with vibrancy, while Hawaiian cultural events honor traditions through music, hula, and storytelling. This mix of refinement and authenticity allows residents to enjoy an active cultural calendar without ever leaving South Maui.

Things to Do in Makena

Outdoor Activities

Makena’s allure lies in its untamed beauty. Makena Beach State Park, home to the famous Big Beach and Little Beach, offers some of Maui’s most iconic coastlines. Big Beach stretches for nearly two-thirds of a mile, inviting sunbathers and surfers alike, while Little Beach embodies Maui’s free-spirited side. Offshore, Molokini Crater, a crescent-shaped volcanic atoll, provides unmatched snorkeling and diving in crystal-clear waters. Kayakers explore lava-rock coastlines and hidden coves, while hikers traverse the surreal lava fields of the Ahihi-Kinau Natural Area Reserve, immersing themselves in landscapes shaped by fire and sea.

Dining & Leisure

Dining in Makena is more understated but no less memorable. Boutique resorts and private clubs anchor the culinary scene, offering intimate farm-to-table dining and menus crafted from locally sourced ingredients. Spa and wellness retreats are an integral part of the experience, blending outdoor adventure with restorative relaxation. Leisure here is not about grand gestures but about subtle luxury, private dinners overlooking quiet beaches, mornings spent at a yoga pavilion, or afternoons unwinding in oceanfront pools framed by volcanic cliffs.

Arts & Cultural Connection

Makena’s cultural spirit is quieter than Wailea’s but deeply rooted in authenticity. Community gatherings and small-scale events celebrate Hawaiian traditions, from oli (chants) and mele (songs) to hula and storytelling. These experiences foster connection, not only with neighbors but with the island’s past, creating a sense of belonging that resonates deeply with residents who choose to make Makena their home.

A Seamless Connection

While Wailea dazzles with resort polish and Makena captivates with natural abundance, the two are inseparable in daily life. Residents move easily between them: a sunrise swim along Wailea’s coastline, a late morning hike through Makena’s lava fields, an afternoon of shopping or spa treatments, and an evening of fine dining back in Wailea. Their proximity allows for a lifestyle that is both dynamic and harmonious, balancing indulgence with simplicity in a way only South Maui can offer.

Making the Move

For many buyers, the dream of owning in Wailea or Makena comes with natural questions. Purchasing property in Hawaii, a destination off the U.S. mainland, can feel daunting at first. Concerns about distance, accessibility, and long-term investment are common, particularly for those considering a second home or seasonal retreat. Yet these hesitations often give way to confidence once the realities of life in South Maui become clear.

Accessibility is rarely an issue. Maui is served by direct flights from major U.S. cities, and Wailea and Makena are only a short drive from Kahului Airport. For many residents, arriving at their island home feels seamless, a transition from city pace to island tranquility that takes only a few hours in the air.

Another common question involves property value. Buyers wonder if investing so far from the mainland carries risk. In reality, real estate in Maui has demonstrated enduring strength, supported by limited land availability and consistent global demand. Wailea and Makena, in particular, remain highly sought after for their exclusivity, natural beauty, and world-class amenities.

Hesitations fade when weighed against mornings spent on golden beaches, evenings dining under starlit skies, and a daily rhythm defined by beauty and balance. With the guidance of a trusted local expert like Kate Peterson, the journey to homeownership becomes not only manageable but deeply rewarding.

Your Connection to Wailea and Makena

When it comes to finding the right real estate in Wailea or Makena, having a connection with the right experience matters. Kate Peterson brings unmatched local insight to every transaction. Backed by the global reach and reputation of Island Sotheby’s International Realty, she provides discerning clients with the guidance, discretion, and market expertise needed to secure exceptional properties. From first conversations to closing day and beyond, Kate ensures your Maui real estate journey is seamless, informed, and tailored to your goals.

Contact Kate Peterson by calling 808.344.7927 or leave a message here. A new adventure is waiting on the sunny shores of Wailea and Makena.