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Wailea Real Estate Search

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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

3100 Wailea Alanui Dr Unit 17, Kihei image
3100 Wailea Alanui Dr Unit 17, Kihei — Papali Wailea $4,795,000

Where do timeless design, ultimate privacy, and panoramic ocean vistas all converge in Wailea? Welcome to Papali #17. Perfectly positioned in the community’s premier loca...

  • 3 Beds
  • 4 Baths
  • 410334 MLS
  • Papali Wailea Bldg.
  • Fee Simple Tenure
Courtesy of Coldwell Banker Island Prop(S)

Listing courtesy of Coldwell Banker Island Prop(S).

5050 Makena Rd, Kihei image
5050 Makena Rd, Kihei $29,900,000

Perched on one of Makena’s most coveted cliffside locations, this contemporary direct-oceanfront estate is perfectly situated along an intimate cove, offering breathtakin...

  • 5 Beds
  • 6 Baths
  • 407766 MLS
  • Fee Simple Tenure
Courtesy of Discovery Makena Realty LLC

Listing courtesy of Discovery Makena Realty LLC.

5412 Makena Alanui Rd Unit 102/KV-3B, Kihei image
5412 Makena Alanui Rd Unit 102/KV-3B, Kihei — Makena Beach Club & Residences $12,500,000

Brand New Luxury Unit - Welcome to your new home, a spacious ground floor, 4-bedroom, 4.5-bathroom unit spanning 3,625 sq ft, nestled within Makena Beach Club and Residen...

  • 4 Beds
  • 5 Baths
  • 407694 MLS
  • Makena Beach Club & Residences Bldg.
  • Fee Simple Tenure
Courtesy of Discovery Makena Realty LLC

Listing courtesy of Discovery Makena Realty LLC.

208 Holomoana Way Unit 14B, Kihei image
208 Holomoana Way Unit 14B, Kihei — Makalii At Wailea $3,695,000

Makali’i Magnificence! Premium top row position with unbelievable Ocean and Outer Island views! Makali’i #14B is arguably the best location in the community with expansiv...

  • 3 Beds
  • 3 Baths
  • 410261 MLS
  • Makalii At Wailea Bldg.
  • Fee Simple Tenure
Courtesy of Hawaii Life (W)

Listing courtesy of Hawaii Life (W).

139 Waaula Way, Kihei image
139 Waaula Way, Kihei $2,499,000

Welcome to 139 Waaula St, a stunning single-family home in the gated Wailea Kai community, just one block from Keawakapu Beach. Set on a large 10,000-square-foot lot, thi...

  • 3 Beds
  • 3 Baths
  • 410251 MLS
  • Fee Simple Tenure
Courtesy of Coldwell Banker Island Prop-Ku

Listing courtesy of Coldwell Banker Island Prop-Ku.

3919 Waakaula Pl, Kihei image
3919 Waakaula Pl, Kihei $3,750,000

Imagine the possibilities! Framed by sparkling ocean, pool and sweeping panoramic views, while perched within one of South Maui's most prestigious enclaves, this 3-bedro...

  • 3 Beds
  • 3 Baths
  • 410226 MLS
  • Fee Simple Tenure
Courtesy of Century 21 Island Homes

Listing courtesy of Century 21 Island Homes.

363 Kai Malu Pl Unit 56B, Kihei image
363 Kai Malu Pl Unit 56B, Kihei — Kai Malu $2,250,000 ▼

Step into this elegant residence, and be met with a magnified view of the ocean! With high end furnishings and window coverings included, flex space downstairs bedroom/of...

  • 3 Beds
  • 3 Baths
  • 410198 MLS
  • Kai Malu Bldg.
  • Fee Simple Tenure
Courtesy of Keller Williams Realty Maui-Ka

Listing courtesy of Keller Williams Realty Maui-Ka.

4000 Wailea Alanui Dr Unit 101, Kihei image
4000 Wailea Alanui Dr Unit 101, Kihei — Wailea Point I Ii Iii $13,900,000

Level One oceanfront at Wailea Point — Hawaii's finest residential condominium, nestled between Wailea Beach and Polo Beach on Maui's coveted Gold Coast. 3,820 SF · 4 bed...

  • 4 Beds
  • 4 Baths
  • 410182 MLS
  • Wailea Point I Ii Iii Bldg.
  • Fee Simple Tenure
Courtesy of Engel & Volkers Maui

Listing courtesy of Engel & Volkers Maui.

30 Kai Malu Dr Unit 201, Kihei image
30 Kai Malu Dr Unit 201, Kihei — La'i Loa $3,895,000

The one you’ve been waiting for at La’i Loa! Pride of ownership shines in this premier 3 bedroom, 3 bath villa, set in the most coveted location of the community. Villa 4...

  • 3 Beds
  • 3 Baths
  • 410170 MLS
  • La'i Loa Bldg.
  • Fee Simple Tenure
Courtesy of Coldwell Banker Island Prop(S)

Listing courtesy of Coldwell Banker Island Prop(S).

4000 Wailea Alanui Dr Unit 1203, Kihei image
4000 Wailea Alanui Dr Unit 1203, Kihei — Wailea Point I Ii Iii $4,500,000

Experience direct oceanfront, front-row living at Residence 1203 in Wailea Point, offering breathtaking, unobstructed ocean views, spectacular year-round sunsets, and fro...

  • 2 Beds
  • 2 Baths
  • 410129 MLS
  • Wailea Point I Ii Iii Bldg.
  • Fee Simple Tenure
Courtesy of Wailea Point Realty, Inc.

Listing courtesy of Wailea Point Realty, Inc..

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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