
The island of Maui is known for its stunning natural beauty, with crystal clear waters, lush tropical foliage, and sweeping views of the Pacific Ocean. And for those looking to live in the lap of luxury, Wailea is the place to be. This upscale resort community is home to some of the most exclusive and expensive real estate in Hawaii, with properties that command prices of $2 million, $10 million, and even $30 million and up. What sets these properties apart from more modest homes on the island? For starters, their locations are nothing short of spectacular. Many of these luxury homes are situated on pristine oceanfront lots, offering unobstructed views of the ocean and nearby islands. Others are perched on hilltops, offering sweeping panoramic views of the coastline and surrounding mountains.
But it's not just the location that sets these properties apart. The level of luxury and attention to detail in these homes is truly unparalleled. From the moment you step through the front door, you'll be greeted by stunning architecture and impeccable design. High ceilings, expansive windows, and natural materials like stone and wood create a sense of grandeur and sophistication. Of course, it's not just the aesthetics that make these properties so special. They're also equipped with all the modern conveniences and state of the art technology you could ever need. From smart home systems to climate controlled wine cellars, no expense has been spared in creating the ultimate luxury living experience.
But perhaps the most unique feature of these high end properties is the level of privacy they offer. Many of these homes are situated on large lots, ensuring that you'll never have to worry about neighbors or noise. And with top of the line security systems and gated entrances, you can rest easy knowing that you and your loved ones are safe and secure. Of course, with prices starting at $20 million and going up from there, these properties are not for the faint of heart. But for those with the means to afford them, they offer a level of luxury and exclusivity that is truly unparalleled. Whether you're looking for a vacation home, a retirement retreat, or simply a place to call your own, Wailea's luxury real estate market has something for everyone. So if you're ready to live the ultimate luxury lifestyle, Wailea's luxury real estate market is waiting for you.
Tucked behind your own personal gate within the exclusive, gated neighborhood of Wailea Kai, 3150 Waiea Pl is a completely private tropical oasis just across the street f...
Listing courtesy of Hawaii Life (W).
Welcome to Wailea Kai, where privacy, luxury, and effortless island living come together in one of Wailea’s most desirable gated communities. This immaculately maintained...
Listing courtesy of Romvari Realty Ltd.
Experience front-row ocean views at Keala O Wailea #4-201, a beautifully positioned 3-bedroom, 2-bathroom residence in one of the most sought-after buildings within the c...
Listing courtesy of Hawaii Life (W).
PERCHED HIGH ON THIS ELEVATED LOT. It is rare that a house in Wailea has an asking price less than the county assessed value with remarkably low real property taxes of on...
Listing courtesy of eXp Realty.
Discover elevated luxury at Villa T-1, the best priced property and sole end-unit available today at Ho’olei. Boasting the community’s largest floor plan—the sought-after...
Listing courtesy of Keller Williams Realty Maui-Ka.
Sublimely located in the exclusive gated community of Wailea Kai, this beautiful single-level home places you just steps from the golden sands of Keawakapu Beach. Owned p...
Listing courtesy of Maui Luxury Real Estate LLC.
Welcome to Maluaka Mauka, an exclusive gated community of just 53 homesites nestled across 28 acres in the heart of Makena. Ideally located just moments from the sandy sh...
Listing courtesy of Discovery Makena Realty LLC.
Welcome to Maluaka Mauka, an exclusive gated community of just 53 homesites nestled across 28 acres in the heart of Makena. Ideally located just moments from the sandy sh...
Listing courtesy of Discovery Makena Realty LLC.
Brand New Construction | Luxurious Estate Living at The Ridge, Wailea Welcome to a sprawling, brand-new estate at The Ridge in Wailea, where every detail has been curated...
Listing courtesy of Hawaii Life (W).
Wailea Beach Villas H102 is a beautifully furnished 2-bedroom, 2-bath residence with a versatile den/office, offering the flexibility for remote work or additional guest ...
Listing courtesy of Hawaii Life (W).
Based on information from the Multiple Listing Service of Hicentral MLS, Ltd. Listings last updated on . Information is deemed reliable but not guaranteed. Copyright: 2026 by HiCentral MLS, Ltd. IDX information is provided exclusively for consumers' personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
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