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—a coastal resort community in
Hawaii—is an opulent vacation spot with a paradise setting on the south coast of the island.
An area known as the Beverly Hills of Maui for its affluence and celebrity draw is a master-planned development with championship golf courses, stately waterfront estates and upscale hotel resorts along its coastline. It’s known for its sunny weather, and its five crescent beaches are frequently voted as some of the best in the U.S.
Featuring many luxury condo complexes, including beachfront ones, Wailea has been developed since the 1970s on lush emerald slopes, rising up from the ocean. It has plenty of surfing spots, mountain views, and ocean-front and hiking trails. The Kalahaku volcano crater looms above it.
“Wailea and neighboring Makena are synonymous with value, exclusivity and custom-home ownership. All of Wailea’s condos would be considered part of the luxury tier of the real estate market,” said Meghan Clair, a real estate agent Coldwell Banker Island Properties in Wailea.
In recent years, Wailea has seen a pandemic-powered spike in property investment. “In 2021-22, there was a sudden increase in sales, shortened days on market, and extremely competitive sales situations often with multiple offers immediately. Many homes sold before even hitting the public market,” Ms. Clair said.
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Wailea lies on the south side of Maui, Hawaii’s second biggest island, known as the valley isle.
Wailea is bordered by Kilohana Drive on the north side, and the Pacific Ocean on the west side. It includes everything west of the Piilani Highway and ends on Kaukahi Street as the southernmost border.
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In Wailea, “entry level for a residential condo is around $1.6 million, while the highest-priced condo on the market currently is $17 million,” Ms. Clair said.
Prices reach well over $40 million for some of the beachfront masterpieces on the water at Maluhia, an exclusive gated development, said Alex Cortez, managing partner, broker-in-charge of Island Sotheby’s International Realty.
But overall, when it comes to single-family homes, the average asking price is currently $4.4 million, with the current highest asking price at $33 million, said Stephen Cipres, founder of Corcoran Pacific Properties.
Wailea is mainly formed of high-end condo communities, including Wailea Beach Villas and Wailea Point.
Most houses in Wailea are custom built and the area still has a number of vacant plots available for single homes. Most date from the 1980s to the 2000s, when the island saw massive development due to a boom in tourism. At the moment, there is a lot of vertical construction and renovation work happening, Ms. Clair said.
Custom-built houses are often a single-level Hawaiian-plantation style design or multi-level modern homes, both of which emphasize indoor-outdoor living.
“Every amenity can be expected, including gated entrances, pools, large gardens, garages, breath-taking ocean and mountain views, highly crafted custom finishes, guest suites, theater rooms, steam baths and saunas, etcetera,” Mr. Cipres said.
What Makes It Unique
“Maui, and Wailea in particular, is one of the most beautiful locations in the U.S., and there are limits to expansion between the mountains and the ocean, such that it will always be a highly coveted place to live, play and work,” Mr. Cipres said.
The island contains two shield volcanoes, rainforests and valleys, pristine beaches, and a humpback whale sanctuary.
“The warm, sunny weather is a constant draw for people looking to enjoy time outdoors while escaping harsh winter conditions,” Mr. Cortez said.
Wailea has both a transient population and a longstanding community. Many homes have been owned for a long time, and there is a great sense of community among property owners, according to agents.
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Wailea has the world-renowned Wailea Golf Club, which includes three award-winning, 18-hole championship courses: the Blue (nicknamed “the Grand Lady”), Emerald and Gold, which was designed by Robert Trent Jones Jr. The club adjoins the Wailea Tennis Club, which has 11 courts open to both residents and visitors.
The area has a three-mile paved coastal path with views of other islands and climbs to Wailea point where you can whale watch from November through to May. It also has a wealth of ocean-based activities, which can be enjoyed year-round.
Wailea Beach has been named among the best beaches in the world “time and time again, but all its beaches are outstanding,” Mr. Cortez said. Wailea’s five main beaches are Polo, Wailea, Ulua, Mokapu and Keawakapu.
The North Shore of Maui, about half an hour away, is a haven for surfing enthusiasts worldwide, with many doing the annual trek to enjoy some of the world’s best surfing. There’s also great surfing in West Maui and South Maui, at beaches in Kaanapali, Lahaina and Kihei. Popular beaches such as Hookipa (35 minutes from Wailea), and Honolua Bay (one hour away) host international surf and windsurfing contests.
Wailea hotels offer world-class spas and wellness centers and five-star dining. The Four Seasons Resort Maui, Grand Wailea, Fairmont Kea Lani and Wailea Beach Marriott are top choices in the area. They are joined by newer properties such as Hotel Wailea and Andaz Wailea.
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Wailea has an abundance of good dining spots, from elegant hotel restaurants to farm-to-table spots, of which there are many on the island.
Most notably, there’s Kō Restaurant at the Fairmont Kea Lani, which serves Hawaiian dishes. Humuhumunkunukuapua’a, meanwhile, is a high-end beachfront bar/eatery at the Grand Wailea resort with Polynesian meat and fish dishes.
Monkeypod Kitchen by Merriman is a farm-to-table restaurant and bar with Hawaiian food, beer and cocktails. Just half an hour away in Paia is Mama’s Fish House, a converted beach house that is regarded as one of the island’s top restaurants.
Wealthy locals with school-age children could opt for the top-ranking Haleakala Waldorf School, which offers education from preschool to grade 12 and is located in Kula about 40 minutes away.
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Who Lives There
The community of Wailea has a mix of full-time and out-of-town buyers, the largest group of which are typically from the West Coast of the U.S. and are purchasing a second home and or an investment property, agents said. There is strong representation from Canadians, particularly from Vancouver and Calgary, Mr. Cortez said.
Recently, there have been buyers from parts of the U.S. not typically seen there before, such as Texas and Minnesota, Mr. Cortez said.
Celebrities who’ve owned homes in the area reportedly include the likes of actor Jim Carrey and musicians Steven Tyler.
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“Wailea has steady property values, even in a rebalancing or shifting market, as owners here are generally equity-rich and know they own something very special. Frankly, we are optimistic that the Wailea market will continue to be one of the strongest segments in Hawaii,” Mr. Cortez said.
The perennial draw of the area’s lifestyle and natural beauty underpin demand outside of unavoidable market pauses, as was seen in the very early days of the pandemic, the agents said.
“This combined with limited inventory suggests our prices will stay firm or climb in the next year,” Ms. Clair added.
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