Wailea Real Estate

71 Listings

Elegant single-family gated communities

Wailea has been planned as a low-density community with extensive green parkland to create an open, expansive aura, assisted by three golf courses, wide beaches, boundless ocean, and lush pasturelands up the slopes of Haleakalā.

For residents wanting to bask full-time in Wailea’s sun and luxury, new single-family gated communities range from an exclusive beach location to further inland and up the rise toward Haleakalā. A few of these neighborhoods wrap around rolling fairways.

Infrastructure is complete, including curbed streets, sidewalks, and streetlights. The custom homes built on spacious lots make the neighborhoods very distinctive.

Several residential communities still have lots available, while new residential complexes are being planned on the few undeveloped areas remaining.

Since 1987, the Wailea Community Association has established design guidelines that have maintained Wailea’s exclusive image while also keeping in character with its tropical location. The association also manages maintenance of Wailea’s common property, seen as a unifying element, keeping the community’s appearance connected, spacious, and pristine.

Most of the homes in these communities have three or four bedrooms. The homes have grown even larger with more development, with 5,000 or more square feet not uncommon.

On the northern edge of the Wailea planned community is the 1,200-acre Maui Meadows community with homes and estates on one-half acre or more properties. There are about 600 homes and a few remaining vacant lots. Home styles here are more varied in size and style but still in keeping with their Hawaiian surroundings.

It is a more country feeling in Maui Meadows, without sidewalks and few streetlights. From its lower western border along Pi’ilani Hwy., the neighborhood rises from 300 ft. above sea level to 650 ft. on its eastern border, enabling more expansive views of the ocean, neighboring islands, and coastline.

Because Maui Meadows borders Ulupalakua Ranch on three sides, homeowners next to the ranch land must install a cattle-proof fence on their adjacent property. However, the views of the distant ranch pasture lands and an occasional visit by cows or a paniolo (cowboy) wrangler just adds to the delightful ambiance of this area.

All residential properties, including condos, in Wailea and Maui Meadows are fee simple.

Condominiums – popular with full-time residents and investors

For many savvy investors, Wailea is a community that draws affluent, discerning vacationers looking for superior accommodations in one of the world’s most luxurious resort destinations. While zoning prohibits Wailea single-family residential communities from hosting vacation rentals, nine of the seventeen current condo communities do allow them.

The seventeen condo communities in Wailea are generally multiple units in two- or three-story buildings, ranging from comfortable to luxurious, or two- or three-story luxury townhomes. These condos are available in one-, two-, three- and four bedrooms and range in size from approximately 500 sq. ft. to over 3,000 sq. ft.

While purpose and size are important factors for buyers, location plays a significant role in the price. The most popular settings are beachfront, cliff-side, beach and ocean overlook, and golf course views. With Wailea’s rising elevation, some complexes have condos on rising terraces to take advantage of spectacular vistas while not obstructing neighbors’ views.

Ekahi Village, built in 1976, is the first condo development built in Wailea. One- and two- bedroom units in two-story buildings sit at various elevations on spacious landscaped property adjacent to the beach. The condo units, many remodeled or renovated, are primarily vacation rentals. They are popular with vacationers, though not as spacious as newer, more luxurious condos.

Besides their luxurious amenities, some of the exclusive condo complexes also have access to affiliated hotel amenities.

Sales in Wailea have been robust, especially in the condo market. An elegant and spacious condo complex completed in 2021 is now completely sold, with a number of its townhomes already on the resale market.

From agriculture to ranch land to a premier resort destination

Along almost two miles of ocean shoreline, the 1,500 acres of Wailea used to be Ulupalauka Ranch grazing land. The ranch began as a farm on smaller acreage leased from Kamehameha III in 1845. After the Great Māhele of 1850 allowing private ownership, former whaling captain James Makee purchased the farm. He brought cattle and cows, along with many agricultural ventures, to the southwestern slopes of Haleakalā. It became Rose Ranch in honor of his wife, who loved roses and grew them on the property.

As time passed, the ranch changed hands a couple of times and grew further in size. Cattle ranching became the primary focus. In 1922, Frank Baldwin acquired the ranch and renamed it Ulupalakua Ranch, the Hawaiian name for the area. Baldwin was part of the family of Alexander & Baldwin fame, one of the "Big Five" families that have driven Hawai’i's economic and political interests in the past and remain prominent today.

In 1957, Matson Navigation Company, the shipping and famous “white ships” cruise line of Hawai’i, purchased the Wailea acreage from Ulupalakua Ranch. Matson wanted to expand its ports of call to Maui and create a large resort/residential community on its new property.

Alexander & Baldwin purchased Matson in the 1960s and eventually scaled down the plans for the area. As timesaving jet travel was on the rise, the seaport idea was scrapped and a new master plan created. After the extensive infrastructure was completed, Wailea construction began in the mid-1970s with two hotels, three condominium projects, a shopping village, tennis club, and the first of its three golf courses.

In the 1980s, residential growth accelerated with more condos and custom homes. From the 1990s to today, two more golf courses, a larger shopping center, and more hotels have been added while existing hotel renovations have been made to continue Wailea’s distinction as a luxury destination. New residential developments have been built, with more planned; however, low density continues to be an essential factor for both developers and the community. As Wailea continues to grow, the Hawaiian ideals of eco-sustainability and cultural community are still important considerations.

Warm weather to enjoy all of Wailea’s outdoor activities

The weather in Wailea is delightful all year round, though sometimes a bit humid in the late summer months, especially if the trade winds aren’t blowing. The average summer high temperature is 87°F(30°C). In the winter, the average high is 80°F(27°C), and the water temperature is 75°F(24°C). No need to don a wet suit to surf in winter here!

January has the most rainy days, averaging less than seven days with partial rain. All the islands are prone to flooding when a heavy storm front passes through, causing heavy run-off from the mountain or volcanic slopes. Wailea can occasionally experience some flooding, but it lies between more susceptible flooding areas to the north and south.

Ocean adventures in calm, inviting tropical waters

Maui offers a lot to see and do, but one doesn’t have to leave Wailea-Makena to enjoy the ocean activities if golf or tennis is not on the agenda. A stroll down to the beach to walk along Wailea’s paved coastal walk, about a mile and a half one way, is a healthy, enjoyable means of checking out the activity on the water and the five beaches. The beautiful scenery is a soothing bonus.

Some condo complexes provide exclusive ocean activities for residents and vacation guests, such as tidepool exploration or swimming with honu (turtles). But several shops offer scuba diving, surfing, kayaking, and stand-up paddling rentals and lessons.

Outrigger canoe paddling and catamaran sails to Molokini or close-up whale watching are a few more ocean activities available in Wailea-Makena. Early morning snorkeling adventures are especially memory-making in the waters off Wailea.

Swimming, boogie boarding, and snorkeling are enjoyed in the waters at all five crescent-shaped beaches and sunbathing on the silky sands! All the beaches have showers and restrooms.

Public schools and private school options

Both public and private schools offer varied educational opportunities, but most require some travel to other parts of the island. The public elementary school serving Wailea is Kamali’i Elementary (PK-5) in Kihei, about two miles from central Wailea.

GreatSchools.org rates the school above average in test scores. There is also a public charter school in Kihei for grades K-12.

The public intermediate school for grades 6-8, Lokelani Middle School, is also in Kihei. GreatSchools.Org rates it as above average overall.

Twelve Christian and private schools in Maui offer PK-8 education. The Montessori School in Kihei is the closest.

Maui High School (9-12) in Kahului currently serves the Wailea community. The school bus ride is approximately 16 miles and 30 minutes. GreatSchools.org rates it average in test scores and below average in college prep. A new state-of-the-art public high school is being constructed in Kihei and scheduled to open in 2023. Greater student involvement is expected with the closer proximity for Wailea students.

Eight Christian and private schools have high schools in Maui. Horizons Academy (5- 12) is a special education school in Haiku.

Upcountry Maui has three notable private high schools: Kamehameha Schools Maui, Haleakala Waldorf School, and Seabury Hall. Sumner Erdman, the owner of Ulupalakua Ranch, is a Seabury Hall graduate.

The University of Hawai’i has a community college campus in Wailuku, also offering online classes.

Urgent care and family practice services in Wailea and Kihei

The medical services in Wailea are somewhat limited. However, Wailea has four Urgent Care offices, one offering house calls. Kihei-Wailea Medical Center in Kihei has a family practice, internal medicine, and pediatric clinic.

Kaiser Permanente has a clinic in Kihei, and Straub (Hawaii Pacific Health) has a clinic in Kahului.

Maui Memorial Medical Center, Wailuku, is the only acute care hospital on the island. It is about 16 miles (30-35 minutes by vehicle) from Wailea. The hospital is affiliated with Kaiser Permanente. US News cites heart failure, stroke, COPD, and pneumonia as Maui Memorial’s high-performance areas.

Four centers for shopping, dining, and real estate and financial services

High-end boutiques, luxury brands, art galleries, and a wide assortment of Hawaiian products are a few of the shops at The Shops of Wailea, the two-story, open-air lifestyle mall. Restaurants, snacks, gourmet foods, and groceries can fill a morning or afternoon exploring the mall and enjoying the sunny outdoors.

The mall has several ongoing Hawaiian events, such as hula, Polynesian shows, lei making, ukulele lessons, woodcarving, and coconut frond weaving. Concerts with Hawaiian artists are also on the event offerings.

Three smaller shopping centers offer a variety of shops, galleries, and services. All the shopping centers offer unique dining experiences, a relaxing change from the bustle of hotel dining.

There are no national fast-food brands in Wailea! All fast-food cravings have to be satisfied in nearby Kihei. For Costco members, the store is in Kahului, near Down to Earth Organic, Lowe’s, and Home Depot.

World-class dining experiences

Delicious dining experiences are all around Wailea, including the shopping centers and golf courses. The Wailea hotels have multi-award-winning restaurants, with lanai settings and unforgettable sunset views. Also, Wailea’s stellar resort destination reputation and discerning vacation guests has drawn notable chefs to its restaurants.

Overall, it would be pretty unusual not to have an extraordinarily delicious fine dining experience.

Many restaurants use locally sourced meats, fish, vegetables, fruits, and other ingredients. Many include updated Hawaiian interpretations of meals and traditional flavors in their dishes. Maui harvested seafood and Maui steak are popular on many menus.

Kō Restaurant at The Fairmont Kea Lani serves Asian-inspired food from Hawaii’s sugar plantation era. It won the 2021 Travelers’ Choice Restaurant Award from Trip Advisor and is a 2022 Conde Nast Traveler Best Restaurant. The menu includes seafood, steak, lamb, pork, and chicken.

Casual dining is a feature of the hotels and shopping centers in Wailea; however, fine dining doesn’t require a top hat and tails (but no “slippahs,” please). Dressing for Wailea’s fine dining can seem downright too casual for those used to a jacket, shirt, and tie, but male residents don’t wear jackets, just a nice aloha shirt and casual slacks. Dare I say that women know how to be tasteful and considerate of other diners in choosing dining apparel? Most do.