Hawaii Real Estate | Hawaii Homes and Condos for Sale
  • Big Island
  • Oahu
  • Maui
  • Kauai
  • Molokai
  • Lanai
Login
808-785-3590

Sign in to your account

Need to reset your phone number?

Don't have an account with us?

Click here to sign up.

Wailea Real Estate Search

TO
Advanced Search

Address Search

Wailea

  

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.

Newest Wailea Listings

3150 Waiea Pl, Kihei image
3150 Waiea Pl, Kihei $2,295,000

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...

  • 3 Beds
  • 3 Baths
  • 410718 MLS
  • Fee Simple Tenure
Courtesy of Hawaii Life (W)

Listing courtesy of Hawaii Life (W).

30 Waikai St, Kihei image
30 Waikai St, Kihei $2,399,000

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...

  • 3 Beds
  • 3 Baths
  • 410693 MLS
  • Fee Simple Tenure
Courtesy of Romvari Realty Ltd

Listing courtesy of Romvari Realty Ltd.

59 Wailea Gateway Pl Unit 4-201, Kihei image
59 Wailea Gateway Pl Unit 4-201, Kihei — Keala O Wailea $2,680,000

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...

  • 3 Beds
  • 2 Baths
  • 410656 MLS
  • Keala O Wailea Bldg.
  • Fee Simple Tenure
Courtesy of Hawaii Life (W)

Listing courtesy of Hawaii Life (W).

221 E Ikea Kai Pl, Kihei image
221 E Ikea Kai Pl, Kihei $2,600,000

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...

  • 4 Beds
  • 4 Baths
  • 410606 MLS
  • Fee Simple Tenure
Courtesy of eXp Realty

Listing courtesy of eXp Realty.

24 Hoolei Cir Unit T-1, Kihei image
24 Hoolei Cir Unit T-1, Kihei — Hoolei $3,850,000

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...

  • 3 Beds
  • 4 Baths
  • 410561 MLS
  • Hoolei Bldg.
  • Fee Simple Tenure
Courtesy of Keller Williams Realty Maui-Ka

Listing courtesy of Keller Williams Realty Maui-Ka.

3111 Waiea Pl, Kihei image
3111 Waiea Pl, Kihei $2,500,000

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...

  • 3 Beds
  • 3 Baths
  • 410525 MLS
  • Fee Simple Tenure
Courtesy of Maui Luxury Real Estate LLC

Listing courtesy of Maui Luxury Real Estate LLC.

112 Manauea St Unit Unit 11, Kihei image
112 Manauea St Unit Unit 11, Kihei $3,025,000

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...

  • 410498 MLS
  • Fee Simple Tenure
Courtesy of Discovery Makena Realty LLC

Listing courtesy of Discovery Makena Realty LLC.

136 Manauea St Unit Unit 9, Kihei image
136 Manauea St Unit Unit 9, Kihei $5,500,000

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...

  • 410497 MLS
  • Fee Simple Tenure
Courtesy of Discovery Makena Realty LLC

Listing courtesy of Discovery Makena Realty LLC.

22 Halapa Pl, Kihei image
22 Halapa Pl, Kihei $7,800,000

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...

  • 3 Beds
  • 4 Baths
  • 410468 MLS
  • Fee Simple Tenure
Courtesy of Hawaii Life (W)

Listing courtesy of Hawaii Life (W).

3800 Wailea Alanui Blvd Unit H102, Kihei image
3800 Wailea Alanui Blvd Unit H102, Kihei — Wailea Beach Villas $4,200,000

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 ...

  • 2 Beds
  • 2 Baths
  • 410442 MLS
  • Wailea Beach Villas Bldg.
  • Fee Simple Tenure
Courtesy of Hawaii Life (W)

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.

Like or Share

Address Search

Search Popular Maui Areas

Looking for the perfect home in the perfect place? Chances are you'll want to check here first:

Maui Luxury Real Estate

  • Maui
  • Central Maui
  • East Maui
  • Haiku
  • Hana
  • Kapalua
  • Kaanapali
  • Kihei
  • Lahaina
  • North Shore Maui
  • South Maui
  • Upcountry
  • Wailea
  • Wailuku
  • West Maui
  • All Maui Communities
  • All Maui Condos

Interactive Map Search

Private Luxury Account

 Exclusive Data Available
 Active Listings Only
 Customizable Search Options
 New Listing Alerts
 Instant Home Value Assessments

Mortgage Calculator

Amount of Loan
Annual Interest Rate
%
Term of Loan
Years
Calculate

Does not include any taxes or fees.
Please consult a financial professional.

 

Connect With Us

     

 

 

MEGACAPITAL HAWAII CORP.

1003 Bishop St. Suite 2700
Honolulu, HI 96813

HAROLD X CLARKE

PAUL ADAMS

(808) 785-3590 Direct

 

© 1999-2026 All Rights Reserved | Site Map | Privacy Policy

 

  FEATURED IN:

 

Advanced Searches

  • Oahu
  • Kahala
  • Honolulu
  • Portlock
  • Kailua
  • Lanikai
  • North Shore
  • Ko Olina
  • Waikiki
  • Big Island
  • Kukio
  • Hualalai
  • Mauna Kea
  • Kohanaiki
  • Mauna Lani
  • Waikoloa
  • Kohala Ranch
  • Kailua Kona
  • Maui
  • Wailea
  • Kapalua
  • Kaanapali
  • Kihei
  • Lahaina
  • Hana
  • Haiku
  • Wailuku
  • Kauai
  • Hanalei
  • Kawaihau
  • Koloa
  • Lihue
  • Waimea
  • Molokai
  • Heights
  • Kahananui
  • Kaluakoi
  • Moana Makani
  • Popohaku Ranchlands
  • Lanai
  • Lanai City
  • Manele
IDX Real Estate Websites by
• Accessibility • Terms • Privacy