Wailea Homes for Sale on Maui's South Shore
Wailea homes for sale span nine gated communities between the Blue, Gold, and Emerald golf courses. Some of Maui’s calmest swim-and-snorkel beaches sit right below them. Homes here range from golf-course residences to oceanfront estates, with pricing from roughly $2 million to well over $10 million depending on location, lot size, and finish.
Many agents selling Wailea’s gated communities work for large mainland franchises, passing buyers between junior agents as the deal moves. We work differently. Billy Jalbert, our principal broker (RB-19015), has sold Maui real estate since 2000 and stays reachable through the whole transaction. Pete Jalbert (RS-68441) moved here from Boulder in 2003 and brings 20-plus years of quarterly market data to every Wailea conversation.
Find your Maui dream home
Contact The Maui Real Estate Team to start your journey toward owning a stunning Maui home.
Maui Real Estate does not sell/distribute your information to third-parties.
What sets Wailea apart on the South Shore
Most off-island buyers start with the same question. What makes Wailea worth the premium? Here’s what the numbers tell us.
9 Communities
3 Golf Courses
$2M to $10M+
What living in Wailea looks like
Wailea's calm South Shore beaches
Wailea is known for its beautiful beaches. Wailea Beach is a one-time Dr. Beach Best Beach in America winner. Ulua, Mokapu, and Keawakapu are known for their good snorkeling, swimming, and general beachgoing. Wailea Elua, Ekahi, Wailea Beach Villas, and Wailea Point are the four condos directly on the beach. Most of the other condos are within walking distance of the beach.
Golf at the center of it all
Living in Wailea means having an abundance of amenities outside your doorstep. Residents have access to three excellent golf courses, The Wailea Tennis Center (offers pickleball too), The Shops at Wailea, fine dining options, and Spa amenities at the hotels. Individual condo developments have amenities, including community pools, fitness centers, and more.
Resort dining and shopping
Wailea offers a broad selection of condos for buyers to choose from. We have mentioned that some permit vacation rentals, and those that prohibit short-term rentals. There are those on the beach and those fronting one of the golf courses. There are long-time favorites in prime locations with low density, like Ekahi, Elua, and Wailea Point. There are also newer complexes with the latest architectural styles and new amenities like Makali’i and La’i Loa. Let us know your priorities and budget, and we can direct you towards developments that might fit your needs.
Gated communities to oceanfront estates
The Makena area is just South of Wailea. In fact, most people think that one of the Makena Condos, Polo Beach, is in Wailea. Na Hale O Makena and Makena Surf are further down the coast, away from the resort hotels. That is one of the draws of the area. It tends to be quieter than Wailea. In addition to the condos mentioned above, the Makena Golf and Beach Club includes a handful of premium condominium developments within the community.
Buying in Wailea is a big decision
Tell us what you’re after and your timeline. We’ll help you weigh location, view, and price, and flag the details most buyers miss before they commit.
Wailea Homes for Sale by Gated Community
Know the Wailea area already, or have a community in mind? Browse homes by neighborhood, or reach out and we’ll point you to the right fit.
For a closer look at the condo market, see our Wailea condos for sale page. Still comparing neighborhoods? Our guide to Maui’s best neighborhoods and Maui cost of living breakdown cover the tradeoffs.
Frequently Asked Questions About Wailea
What's it like to live in Wailea year-round?
Plenty of owners live in Wailea full time, not just seasonally. You get steady sun, calm beaches, and the Shops at Wailea for groceries and dining nearby. It suits both full-time residents and second-home owners.
How many gated communities are in Wailea?
Wailea has nine gated communities, spread between the golf courses and the coast. They range from golf-course neighborhoods to oceanfront enclaves. We can walk you through how each one differs in feel, lot size, and setting.
What's the difference between a Wailea golf-course home and an oceanfront estate?
Golf-course homes sit along the Blue, Gold, or Emerald fairways, often with mountain and sunset views. Oceanfront estates trade that for direct water frontage and a higher price point. We’ll show you both so you can compare in person.
Is Wailea or Makena a better fit for a luxury buyer?
Wailea is the resort core, with golf, beaches, and dining close together. Makena sits just south and trades that for more space and seclusion. The right fit depends on how private you want to be, and we can show you both.
How far is Wailea from the airport and the rest of Maui?
Wailea sits on Maui’s South Shore, about a 35 to 45 minute drive from Kahului Airport depending on traffic. Kihei and its shops are a few minutes north. Most of the island stays within an easy day trip.
How do I start a Wailea home search from off-island?
Tell us what you’re after and your timeline. We’ll set up listing alerts, talk through each community, and line up showings when you visit. Many of our clients research for a year or more before they buy.