This stunning contemporary estate spans 6,517 square feet of refined luxury, featuring five spacious bedrooms and five and a half beautifully appointed bathrooms. Designe...
Listing courtesy of Discovery Makena Realty LLC.
Located at the end of a peaceful cul-de-sac and bordering a lush greenbelt, this exceptionally designed 4 bedroom, 2.5 bathroom home in the prestigious Wailea Kialoa comm...
Listing courtesy of Hawaii Life (W).
Discover a rare chance to create your legacy in Maluaka Estates, an intimate, private gated enclave of only 13 custom estates in the heart of Makena. Just moments from th...
Listing courtesy of Discovery Makena Realty LLC.
Welcome to this beautiful 2-bedroom, 2-bathroom condo at Wailea Fairway Villas, offered fully furnished and move-in ready. Enjoy breathtaking ocean views and spectacular ...
Listing courtesy of Coldwell Banker Island Prop-Ku.
Wailea Elua Unit 2010 presents an exceptional opportunity to own in one of Wailea's most coveted beachfront communities. Ideally positioned on the second floor, this 2 be...
Listing courtesy of Island Sotheby's International Realty(W).
Discover one of Wailea's rarest offerings ; a beautifully appointed ground-floor residence that pairs effortless access with exceptional views. This stunning 2-bedroom co...
Listing courtesy of Hawaii Life (W).
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...
Listing courtesy of Coldwell Banker Island Prop(S).
Perched on one of Makena’s most coveted cliffside locations, this contemporary direct-oceanfront estate is perfectly situated along an intimate cove, offering breathtakin...
Listing courtesy of Discovery Makena Realty LLC.
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...
Listing courtesy of Discovery Makena Realty LLC.
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...
Listing courtesy of Hawaii Life (W).
Discover epic island living at an incredible value in the Wailea Resort. Wailea Fairway Villas S202 is one of the best view locations in the community, capturing breathta...
Listing courtesy of Coldwell Banker Island Prop(S).
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...
Listing courtesy of Coldwell Banker Island Prop-Ku.
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...
Listing courtesy of Century 21 Island Homes.
The Ultimate Ocean View You’ve Been Waiting For at Wailea Ekolu #1706! Enjoy upper floor privacy with absolutely amazing ocean and outer island views from this recently r...
Listing courtesy of Hawaii Life (W).
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...
Listing courtesy of Keller Williams Realty Maui-Ka.
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...
Listing courtesy of Engel & Volkers Maui.
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...
Listing courtesy of Coldwell Banker Island Prop(S).
Experience direct oceanfront, front-row living at Residence 1203 in Wailea Point, offering breathtaking, unobstructed ocean views, spectacular year-round sunsets, and fro...
Listing courtesy of Wailea Point Realty, Inc..
Welcome to 3236 Pikai Way, an exceptional single-level residence nestled within the exclusive gated enclave of Wailea Kai, just across the street from the golden sands of...
Listing courtesy of Kokua Realty LLC.
Every once in a long while, a home feels less like a property and more like a discovery. Rebuilt from studs in 2019, this better than new single level, no steps Wailea re...
Listing courtesy of Maui Luxury Real Estate LLC.
Can't find what you're looking for? Take advantage of this rare corner lot to build your dream Maui home ! Located near the center of the prestigious Wailea Golf Vistas g...
Listing courtesy of Coldwell Banker Island Prop(S).
Secluded location, extensive upgrades, amazing price! Welcome to Grand Champions #30, a top-floor corner 2-bedroom, 2-bath Tennis Villa with a lock-off option, offering o...
Listing courtesy of Coldwell Banker Island Prop-Ku.
Rarely does an opportunity like this come along at Wailea Ekahi. This beautifully positioned downstairs 1-bedroom, 2-bathroom villa enjoys stunning ocean views and sits i...
Listing courtesy of Hawaii Life (W).
La'i Loa: Where Elevated Design Meets the Spirit of Wailea THIS UNIT IS AVAILABLE TO VIEW FOR PRIVATE SHOWINGS ONLY! There are homes that offer a view, and there are h...
Listing courtesy of Keller Williams Realty Maui-Ka.
Nestled within the prestigious Wailea Pualani community, 390 Pualoa Nani Place offers the essence of luxury island living with privacy, elegance, and the relaxed sophisti...
Listing courtesy of Engel & Volkers Maui.
Whether you're seeking a high-performing vacation rental, a lock-and-leave second home, or a comfortable full-time residence, Wailea Ekolu #1204 offers exceptional value ...
Listing courtesy of Coldwell Banker Island Prop(S).
This beautifully appointed 1-bedroom, 2-bathroom condo offers serene ocean views from a private, quiet location within Wailea Ekahi. Wailea Ekahi #17A features an invitin...
Listing courtesy of Hawaii Life (W).
Immerse yourself in the essence of Hawaiian paradise at Grand Champions Villa Unit 74, a desired top-floor gem perfectly situated in the uppermost section of the complex....
Listing courtesy of Coldwell Banker Island Prop(S).
Welcome to one of Maui's best kept secrets. This exceptional Kai Malu residence offers gorgeous ocean views from the primary suite and both lanais. The home is offered fu...
Listing courtesy of eXp Realty.
A rare and extraordinary opportunity in coveted Makena awaits. Just steps from world famous Makena Beach (Big Beach). This exceptional vacant lot spans approximately 28,...
Listing courtesy of Hawaii Life (W).
Experience elevated island living in this beautifully appointed condominium at Lai Loa Wailea, one of South Maui’s newest luxury communities. Purchased new in 2024, this ...
Listing courtesy of Island Sotheby's International Realty(W).
Experience elevated island living at La‘i Loa Wailea, Wailea’s newest luxury condominium development, in this beautiful 2-bedroom, 2-bath 1,374 sq. ft. residence offering...
Listing courtesy of Polaris Pacific.
A private Wailea Kialoa retreat, where chic island elegance meets effortless living. This custom single-level 3-bedroom, 3.5-bath residence offers an open and thoughtfull...
Listing courtesy of Coldwell Banker Island Prop(S).
Experience luxury living at 115 Kai La Place, Kai Malu Maui. This beautifully remodeled furnished 3 bedroom, 2.5-bath residence features a primary suite on the first floo...
Listing courtesy of Coldwell Banker Island Prop(S).
Welcome to modern Hawaiian luxury at Keala o Wailea Unit 4-101. This rare 3-bedroom, 2-bathroom residence offers effortless single-level living with absolutely no stairs...
Listing courtesy of Hawaii Life (W).
$1179.49 HOA fees Located in Wailea, this quiet and serene ground-level 2- bedroom, 2 bath condo is within walking distance of the beach and close to many convenient sh...
Listing courtesy of Nathalie Mullinix Rlty Universal Inc.
Experience the beauty of Wailea resort living from this well-positioned "C" model at the Palms at Wailea. Unit 1509 offers 1,242 square feet of interior living space comp...
Listing courtesy of Coldwell Banker Island Prop-Ku.
Also listed as Condo MLS# 409467. In the best location in Kanani Wailea, adjacent to expansive open space and unobstructed ocean views, this exceptional single-level resi...
Listing courtesy of McEntire Realty.
Ocean, Molokini, and Wailea Blue Golf Course views set the tone from the moment you arrive. This 2-bedroom, 2-bath Wailea Ekolu condo offers a quiet, private setting tuck...
Listing courtesy of Coldwell Banker Island Prop-Ku.
Also listed as Residential MLS# 409490. In the best location in Kanani Wailea, adjacent to expansive open space and unobstructed ocean views, this exceptional single-leve...
Listing courtesy of McEntire Realty.
Best Value in Wailea! Come fall in love with this beautifully remodeled Wailea Fairway Villas second floor unit. Attention to detail is evident throughout from the abunda...
Listing courtesy of Berkshire Hathaway Maui Prop-W.
Wailea Point Residence 802 & 804 is an exquisite, rare, double residence featuring 5 bedrooms and 6 full bathrooms. Enjoy unobstructed panoramic ocean and sunset views fr...
Listing courtesy of Wailea Point Realty, Inc..
Wailea Ekahi 37C is a beautifully updated ground-floor 1 bed / 2 bath condo in the highly desirable oceanfront Wailea Ekahi community. The 2019 remodel includes granite c...
Listing courtesy of Hawaii Life (W).
Wailea Point 2101 is a rare, single-level residence featuring 2 bedrooms and 3 bathrooms with the convenience of no-stair entry. Enjoy breathtaking ocean and garden views...
Listing courtesy of Wailea Point Realty, Inc..
Ocean view residence at Makali'i at Wailea, offered fully furnished with a custom modern interior package. This thoughtfully designed home features contemporary finishes,...
Listing courtesy of Island Sotheby's Int'l Rlty(W).
This charming, private ground-floor 1-bedroom, 1-bathroom end-unit is flooded with natural light and has been meticulously maintained. From the spacious living area, kitc...
Listing courtesy of Coldwell Banker Island Prop-Ku.
Vacant canvas located in one of Maui's most desirable neighborhoods in Wailea. Large 10,890 square foot lot with plans to build a custom 3100 sq ft family oriented home ...
Listing courtesy of Pacific Shores Realty.
Set within the prestigious Wailea Pualani Estates, this 3-bedroom, 2.5-bath residence with an additional office/media room offers refined island living with a seamless in...
Listing courtesy of Compass-W.
Welcome to Makalii one of Wailea’s newest luxury residences known for its mid-century modern design. This spectacular condominium (7C) is located on the upper row and is ...
Listing courtesy of Hawaii Life (W).
Welcome to your serene escape in the heart of paradise! Grand Champions unit #10 is a 2-bedroom, 2-bath condominium with a lock off option creating multiple living or ren...
Listing courtesy of Coldwell Banker Island Prop(S).
The One You’ve Been Waiting For! This pristine, second floor 2 Bedroom 2 Bath unit in Wailea’s Newest Development has it all. This premium location provides you with amaz...
Listing courtesy of Hawaii Life (W).
Andaz Residences Unit 801 (F2) offers a rare opportunity to own one of the coveted private villas at the Andaz Maui Wailea Resort. Ownership combines the privacy of an oc...
Listing courtesy of Coldwell Banker Island Prop(S).
Discover the perfect blend of comfort, style, and location at Palms at Wailea #1207. This beautifully updated 2-bedroom, 2-bath ground-level condominium enjoys a prime po...
Listing courtesy of Hawaii Life (W).
Welcome to Wailea Elua, an exclusive oceanfront, hotel-zoned vacation rental set atop a lush greenbelt in prestigious Wailea. Spanning 24 acres of tropical paradise, this...
Listing courtesy of Coldwell Banker Island Prop(S).
Stunning 2-bedroom, 2-bath upper-level furnished unit with beautiful ocean/sunset and golf course views. Remodeled in 2014, features include new window treatments, tile, ...
Listing courtesy of Hawaii Life (W).
Keala O Wailea 5-103 offers panoramic Pacific Ocean views from one of Wailea's premier hillside communities. This single-level 2-bedroom, 2-bathroom residence spans appro...
Listing courtesy of Coldwell Banker Island Prop(S).
Experience modern island living at Makalii 8A, a 3-bed, 3-bath contemporary townhome tucked away in a quiet corner of the complex, featuring refined new construction in t...
Listing courtesy of Coldwell Banker Island Prop(S).
Over an acre of direct beachfront in Makena is an exceptional rarity — and 4584 Makena Road stands as one of the most compelling value opportunities along Maui's coastlin...
Listing courtesy of Island Sotheby's Int'l Rlty(W).
Perfectly positioned in Wailea Ekolu! The incredible ground floor 2 Bedroom 2 Bath Vacation Rental in the Heart of Wailea you’ve been waiting for is here. Located in Buil...
Listing courtesy of Hawaii Life (W).
E Komo Mai and welcome to Ho'olei 21-4, an elegant 3 bed, 3.5 bath townhome located in the heart of Wailea, Maui. This Hotel Zoned property boasts wonderful ocean views a...
Listing courtesy of Hawaii Life (W).
Finally, a top-floor unit at Elua Village with a garage. Enjoy the rare combination of a preferred floor plan, ocean view, expansive lanai, and a private garage that is j...
Listing courtesy of Wailea Vacation Rentals.
Incredible 2021 pricing for this DREAM LOCATION at pet friendly KAI MALU with this RARE Developer Unit! Breathtaking views - this is Kai Malu at its best. Beautifully ap...
Listing courtesy of Keller Williams Realty Maui-Ka.
Makalii at Wailea 17B is a standout villa commanding the premier ocean-view position in the entire development, offering unobstructed, sweeping vistas of the Pacific, Mol...
Listing courtesy of Coldwell Banker Island Prop(S).
Wailea Palms 3507 is an exquisitely remodeled 2-bedroom, 2-bathroom residence offering serene ocean views and a lush tropical backdrop. Tucked away in a secluded, private...
Listing courtesy of Coldwell Banker Island Prop(S).
You Deserve To Own & Experience Your Oceanfront Paradise Today! Unit 3404 is a delightful 2 bedroom, 2 bathroom upper-level, privately located, & meticulously maintained ...
Listing courtesy of Maui Real Estate Advisors LLC.
A TIMELESS, light-filled OCEAN VIEW residence designed for indoor/outdoor Maui living, this ELEGANT 3-bedroom plus office (possible 4th bedroom) & add'l den, 4-bath home ...
Listing courtesy of Maui Real Estate Advisors LLC.
This exclusive opportunity is uniquely situated on a lot like no other, overlooking the 11th green of the Wailea Blue Course and positioned near the Four Seasons and Hote...
Listing courtesy of Hawaii Life (W).
The newly completed Wailea estate blends contemporary design with Maui’s natural beauty. Ocean-view living with seamless indoor-outdoor flow, abundant natural light, and ...
Listing courtesy of Coldwell Banker Island Prop-Ku.
Wailea Kai is one of the closest communities to the beach! 3 BR 2.5 BA with a pool and easy walking distance to Keawakapu Beach. This recently updated home offers a uniqu...
Listing courtesy of Coldwell Banker Island Prop-Ku.
Relax and Enjoy Ultimate Privacy! Enter your new Wailea place of peace, serenity and tranquility. This 2 Bedroom 2 Bath Vacation Rental Condo has been beautifully renovat...
Listing courtesy of Hawaii Life (W).
Set on approximately ±0.5 acres (20,573 sq ft), this exceptional gated property offers unobstructed ocean views in one of South Maui’s most coveted locations—directly acr...
Listing courtesy of Discovery Makena Realty LLC.
Where the ocean whispers at your doorstep & refined luxury defines every detail, Wailea Beach Villas K-208 presents a rare chance to own a Premier Beachfront retreat with...
Listing courtesy of Maui Real Estate Advisors LLC.
SUNSETS WITH ALOHA . . . . Original Owner| First Time Ever on the Market| Never Rented| Immaculate Condition| Fully Furnished| 3 Bedroom Suites| 3 Full Bathrooms. WBV Pen...
Listing courtesy of Compass-W.
NEXT LEVEL LUXURY . . . The Crown Jewel of Wailea Golf Estates II . . . The most exciting new luxury release to hit the market. A brand new single-level oceanview smart h...
Listing courtesy of Compass-W.
MAKENA RANCH -160 ACRES OF OCEANVIEW LEGACY LAND Offered at $37 Million I Fee Simple Makena Ranch encompasses approximately 160 acres across 13 agricultural-zoned parce...
Listing courtesy of Coldwell Banker Island Prop-Ku.
Discover luxury resort living in this exceptional ocean-view Villa located within the prestigious gated community of Ho'olei in Wailea. It is ideally positioned near worl...
Listing courtesy of Coldwell Banker Island Prop(S).
Wailea Elua beachfront estate on the famed Ulua Beach with endless ocean vistas. Spacious, quiet and private - this upgraded Wailea Elua gem is located at the top of this...
Listing courtesy of Century 21 Island Homes.
Wailea Palms #3202 boasts a private location in the complex overlooking meticulously manicured lawn, gardens and putting green where one can enjoy splendid sunsets, perfe...
Listing courtesy of Coldwell Banker Island Prop-Ku.
Wailea Point Beach Condo 2904 is designed for comfort and relaxation. Wailea Point! South Maui's most elegant, luxurious, and private community. This premier oceanfront...
Listing courtesy of Coldwell Banker Island Prop(P).
Welcome to Wailea Ekolu 105. Easy access to this beautifully remodeled luxury ground floor 2B/2B unit. Condo enjoys the luxury of panoramic ocean and outer island views f...
Listing courtesy of Coldwell Banker Island Prop(S).
Welcome to Wailea Beach Villas Penthouse 209, one of Wailea’s most prestigious gated, Hotel-Zoned beachfront communities. This spacious 3 Bedroom, 3 Bathroom + DEN (confi...
Listing courtesy of Keller Williams Realty Maui-Ka.
AMAZING OPPORTUNITY!!! Where the Ocean Becomes Your Backdrop and Wailea Becomes Your Everyday. Wailea Town Center C-203 is a rare offering, including dedicated garage, bl...
Listing courtesy of Maui Real Estate Advisors LLC.
Positioned in the coveted front row of Wailea Point, Residence 502 sits just 75 feet from the surveyed shoreline, offering commanding southwest-facing views of Molokini C...
Listing courtesy of Wailea Point Realty, Inc..
FABULOUS world class Wailea Point “double” unit with a MOST DYNAMIC ocean & beach front location. Perhaps the finest condominium residence in Hawaii, no expense was spar...
Listing courtesy of Wailea Point Realty, Inc..
A 'WORK OF ART’. A 'LEGACY PROPERTY'. An ‘Equity Location’. A luxurious marriage of two Wailea Point oceanfront units at Maui's finest Condominium Project! When a lifelon...
Listing courtesy of Maui Real Estate Advisors LLC.
Meticulously maintained 3 bedroom 2.5 bathroom Ocean and Mountain View Kai Malu unit with new plush carpets upstairs, luxury vinyl floors downstairs, beautiful epoxy two ...
Listing courtesy of Berkshire Hathaway Maui Prop-W.
Discover Unbeatable Wailea Value Experience the perfect blend of affordability and luxury in the prestigious Palms at Wailea. This inviting, turnkey furnished, ground-lev...
Listing courtesy of Island Sotheby's International Realty(W).
Welcome to this stunning top-floor oceanfront residence in the exclusive Penthouse building at Wailea Beach Villas. This tranquil 2-bedroom, 2-bath villa offers over 2,00...
Listing courtesy of Coldwell Banker Island Prop-Ku.
From the moment you enter Wailea Point 1904, the world seems to pause. Before you lies a sea of liquid blue: waves shimmering under the sun, clouds drifting like silk acr...
Listing courtesy of Maui Real Estate Advisors LLC.
THE BEACHFRONT VILLA - A once in a generation oceanfront sanctuary! The sophisticated remodel completed in January 2025 transformed the B-101 front row Villa into one of ...
Listing courtesy of Compass-W.
Discover Grand Champions 111, a beautifully updated 2-bedroom, 2-bath condominium in the heart of Wailea. This spacious and fully furnished unit offers an inviting open f...
Listing courtesy of Hawaii Life (W).
Motivated Seller — Unbeatable Wailea Value Steps from Keawakapu Beach! The seller is highly motivated, presenting an extraordinary opportunity to secure a beautifully upg...
Listing courtesy of Compass-W.
La’i Loa Luxury with Outstanding Ocean View! Wailea’s Newest Development and your golden opportunity to have it all is here! This gorgeous Turnkey Residence in La’i Loa c...
Listing courtesy of Hawaii Life (W).
Welcome to 139 Kai La Place at Kai Malu -- a 3-bedroom, 2.5 bath townhouse beautifully upgraded with new (2025) wide-plank vinyl flooring, new carpeting, and more! Owner...
Listing courtesy of Hawaii Life (W).
Truly one of Wailea's pinnacle properties, Wailea Elua 803 defines single-level luxury living, with a full-scale remodel encompassing the finest in surfaces and amenities...
Listing courtesy of Keller Williams Realty Maui-Ki.
An absolutely exquisite property in every way, Residence 2802 at Wailea Point boasts a fabulous location with breathtaking ocean, island, beach and coastal views facing i...
Listing courtesy of Wailea Point Realty, Inc..
If you’re looking for the ultimate Maui property, this is it! This luxury top-floor condo at the highly sought-after Palms at Wailea puts you just steps from the spectacu...
Listing courtesy of Coldwell Banker Island Prop(S).
Stunning ocean view, overlooking the Wailea Blue Golf Course, this gem is beautifully positioned in one of Wailea’s most sought-after resort communities—Grand Champions. ...
Listing courtesy of Romvari Realty Ltd.
Located in the desirable gated community of Wailea Kialoa, this 4-bedroom, 3-bathroom home offers convenient access to everything you could want. It's just a short stroll...
Listing courtesy of Hawaii Life (W).
Wailea’s Best Kept Secret! Discover the perfect blend of privacy, comfort, and resort living in this rarely available Wailea townhome. Designed to live like a single-fam...
Listing courtesy of Maui Luxury Real Estate LLC.
Welcome to Kai Malu 43B, beautifully remodeled in 2024, this 3-bedroom, 2.5-bathroom home offers unparalleled privacy, a spacious outdoor area and breathtaking views of ...
Listing courtesy of Coldwell Banker Island Prop(S).
Located in the heart of Wailea, this beautifully maintained 1-bedroom, 2-bathroom ground-floor unit offers the perfect blend of comfort, privacy, and convenience. Situate...
Listing courtesy of Keller Williams Realty Maui-Ki.
Perched atop the exclusive and private enclave of The Ridge at Wailea, this extraordinary Guy Dreier-designed residence is a rare expression of contemporary architecture ...
Listing courtesy of Hawaii Life (W).
Wailea Ekolu #1008 offers the pinnacle of Wailea living—an immaculate upstairs 2-bedroom, 2-bathroom condo with panoramic ocean views. This spacious, end-unit residence f...
Listing courtesy of Coldwell Banker Island Prop(S).
Step into a world of refined elegance and beachfront luxury in Maluhia at Wailea—a sanctuary within Wailea’s most exclusive beachfront enclave. Tucked behind the gates of...
Listing courtesy of Hawaii Life (W).
Experience breathtaking ocean views and unforgettable sunsets from the comfort of your private lanai. This exceptional ground-floor villa is nestled in a highly sought-af...
Listing courtesy of Maui Luxury Real Estate LLC.
This lovely remodeled and cared for 2 bedroom/2 bathroom Grand Champions unit speaks of Hawaiiana and is being sold 'Turn Key' Furnished. Unit #140 is upper-level with va...
Listing courtesy of Maui Real Estate Advisors LLC.
Nestled along the prestigious Makena coastline, 7595 Makena Road represents the pinnacle of contemporary Hawaiian luxury living. This extraordinary residence stands as a ...
Listing courtesy of Compass-W.
OUTSTANDING VALUE for one of Wailea Point's most FABULOUS VIEW UNITS. This is the highly sought after Upper Level D plan, Wailea Point’s second largest standard floor pla...
Listing courtesy of Wailea Point Realty, Inc..
Revel in luxury from an expansive and private oceanfront condo with the best amenities in its class. The spacious, elegant, and bright two-story residence offers a large ...
Listing courtesy of Coldwell Banker Island Prop(S).
Welcome to Wailea—the crown jewel of South Maui and arguably the most prestigious master-planned resort community in the world. When you drive into Wailea, the landscape shifts. The roads become wider and more manicured, the bougainvillea blooms a little brighter, and the sense of arrival is absolute. This is where the world’s most discerning travelers and investors come to find their sanctuary.
When you begin exploring Wailea Real Estate, you'll quickly realize that you aren't just looking at properties; you are looking at a highly curated way of life. At Maui.RealEstate, we recognize that the pursuit of Luxury Wailea Real Estate is about securing a lifestyle and a financial legacy. Navigating this market requires more than just a search bar; it requires a partner who understands the nuances of individual gated communities, the history of land ownership, and the evolving regulations of the 2026 marketplace. Whether you are seeking a penthouse with unobstructed Pacific views or a custom estate on the fairway, our team is here to ensure your Wailea journey is as seamless as a sunset over Molokini.
Curious what your Wailea home is worth? Get answers fast with maui.realestate. Choose a quick instant home value estimate for an immediate snapshot, or book a professional in-home valuation for a detailed market analysis tailored to your property.
Wailea is a 1,500-acre master-planned community that serves as a blueprint for luxury tropical living. Unlike other resort areas that can feel transient, Wailea has a deeply rooted residential soul. It was designed to harmonize with the natural contours of the South Maui coastline, ensuring that almost every property enjoys a piece of the "Wailea Blue"—that specific, deep azure of the Pacific that contrasts so perfectly with the golden sands.
The lifestyle here is defined by ease. Because the area is self-contained, you live in a world of "and." You can have high-end fine dining and wild, untouched coastal trails. You can have championship golf and some of the best snorkeling in the islands. The microclimate is one of Wailea’s greatest assets; sitting in the "rain shadow" of Haleakalā, it enjoys more sunny days than almost any other residential area on Maui, cooled by the gentle trade winds that keep the afternoons perfect for the beach or the links.
In the luxury real estate market of 2026, savvy investors are looking for two things: stability and scarcity. Wailea offers both in spades. While other markets may fluctuate based on global economic shifts, Wailea has historically acted as a "safe harbor" for capital.
Wailea is a global brand. Just as investors look to Beverly Hills, Aspen, or St. Barts, they look to Wailea. This global recognition ensures a perpetual pool of buyers. Even in 2026, where luxury buyers have become more selective, the demand for Wailea properties remains constant. When you buy here, you are buying into an asset class that has shown remarkable resilience and long-term appreciation.
In light of recent Maui County legislation, Wailea stands out because much of it is located within the Hotel/Resort Zone. This provides a layer of protection for owners who wish to utilize their properties as high-end vacation rentals. In a market where rental regulations are tightening elsewhere, the ability to generate short-term income in Wailea is a massive value-add that continues to drive property prices.
Wailea is nearly built out. There are very few remaining "raw" parcels of land. In real estate, when supply is capped and demand is global, the result is upward pressure on value. Investing in Wailea in 2026 is about securing a piece of a finite resource before the "gate" closes on new development.
Wailea’s residential inventory is diverse, offering something for every type of luxury buyer. Understanding the "vibe" of each neighborhood is essential:
In Wailea, the "outdoor lifestyle" isn't a marketing slogan; it’s a daily reality. The community is built around a series of five distinct crescent beaches, each connected by the Wailea Beach Path—a 1.5-mile paved trail that is the heartbeat of the community.
Wailea was designed for the active sophisticated traveler. The amenities here are simply unparalleled in the state of Hawaii.
Wailea offers a level of convenience that makes it a highly livable primary residence. You don't have to leave the resort to find world-class amenities.
While Wailea is often associated with retirees and second-home owners, it is an increasingly popular choice for families who want a safe, active environment for their children.
As we navigate 2026, the Wailea market has reached a new level of sophistication. Within the sector of Luxury Wailea Real Estate, buyers are no longer just looking for a "vacation home"; they are looking for "Residential Resorts."
Ultimately, people choose Wailea because it represents the "Best of the Best." It is a community that has been curated over decades to provide a specific level of excellence. Whether it’s the way the grass is cut along the median or the way the security guard greets you at the gate, everything in Wailea is designed to make you feel like you are exactly where you are supposed to be.
For the investor, it’s a smart move. For the family, it’s a legacy. For the retiree, it’s a reward. Wailea is the rare place where the lifestyle you’ve dreamed of matches the financial sense you’ve worked for.
The Wailea lifestyle is calling. From the first tee at the Gold Course to the last light of a Pacific sunset, the rhythm of life here is both peaceful and exhilarating. Whether you are drawn by the oceanfront condos, the fairway estates, or the world-class amenities, Wailea Real Estate offers the ultimate expression of Maui living.
Stay informed on the latest trends in the Wailea real estate market. As local Wailea experts, we know the area's homes, condos, and neighborhoods inside and out—and can help you make the best decisions whether you're buying or selling in today’s market. Contact us for questions or to request more detailed market statistics.
Discover the best places to live on Maui from world-class beach resorts and golf communities to charming Upcountry retreats. Explore each region and its unique neighborhoods to find the perfect fit for your Maui lifestyle and real estate goals.
Explore Maui's full spectrum of neighborhoods—from sun-soaked beachfront communities and quiet harbor villages to cool Upcountry enclaves and remote East Maui hideaways. Each pocket of the island carries its own character, climate, and real estate mix, so browse the complete list below to discover the neighborhood that best matches your lifestyle, budget, and investment goals.
Maui's condo landscape spans oceanfront resort residences in Kaanapali and Wailea, beachside vacation retreats in Kihei and Napili, affordable townhome communities Upcountry, and boutique low-rises across the island. Browse every major condo building on Maui to compare amenities, locations, and current inventory—and find the property that fits your use case, whether primary residence, second home, or investment rental.
Make your Wailea dream home a reality with maui.realestate. Whether you’re buying a beachfront retreat, selling a luxury estate, or investing in a vacation property, our team delivers deep local expertise, market insight, and a smooth, stress-free process from start to finish. From Wailea and Kihei to Upcountry and beyond, discover how our proven strategies help you buy confidently and sell for top value.
Christopher Barca, a founding member of Compass Hawai’i and one of Maui’s top agents, brings decades of real estate expertise and over 25 years of island living. With a background in film location management and education from Manhattan’s School of Visual Arts and the University of Hawai’i, he offers unmatched market knowledge, a keen eye for design and architecture, and a talent for showcasing a property’s true potential. As a member of the Compass Sports & Entertainment Division, Chris provides world-class marketing and guidance for everyone from first-time buyers to seasoned investors, all while staying laid-back, passionate, and deeply connected to Maui’s business and creative communities.
