Wailea Real Estate

Wailea Real Estate

Welcome to Wailea, a stunning gem nestled on the southern coast of Maui, Hawaii. This luxurious neighborhood, part of the vibrant Kihei community, offers an unparalleled blend of natural beauty, upscale living, and a laid-back island lifestyle.

Wailea is renowned for its breathtaking beaches, including the pristine Wailea Beach, where golden sands meet crystal-clear waters, creating the perfect backdrop for sunbathing, swimming, and snorkeling. The area is also home to several world-class golf courses, making it a haven for golf enthusiasts looking to tee off against the stunning Pacific Ocean.

Beyond its natural beauty, Wailea boasts an array of high-end resorts, gourmet dining options, and boutique shopping experiences. Whether you’re indulging in a farm-to-table meal at a beachfront restaurant or exploring the local art galleries, there’s something for everyone in this vibrant community. The Wailea Village Shopping Center offers a delightful selection of shops and eateries, perfect for a leisurely afternoon out.

For those seeking an active lifestyle, Wailea offers numerous hiking trails, water sports, and wellness activities, including yoga on the beach. The neighborhood is also known for its strong sense of community, with various events and gatherings that bring residents together.

With its picturesque landscapes, luxurious amenities, and welcoming atmosphere, Wailea is not just a place to live – it’s a lifestyle. Whether you’re looking to relax in paradise or engage in outdoor adventures, Wailea is the perfect destination to call home. Experience the magic of Maui in this enchanting neighborhood, where every day feels like a vacation.

Newest Listings in Wailea

$1,149,000
2 Beds ⋅ 2 Baths ⋅ 410776 MLS ⋅ Fee Simple Tenure ⋅ Grand Champions BLDG.
The one you’ve been waiting for at Grand Champions: Unit #29! Rarely do these ground floor corner locations become available in the community. From top to bottom, this villa has so much to offer. With beautiful views of Haleakala, this home is conveniently located on the tranquil, back end of the complex. The covered lanai looks east over the Wailea Blue Golf Course, and offers homeowners the utmost privacy. This is the most highly sought after floor plan in the neighborhood with the flexible “lock off” feature. There are 2 roomy primary-suites, each with spacious bathrooms and separate entrances. The possibilities are endless. However you choose to utilize the space, you will enjoy the masterful owner upgrades and unique position of this condo. This end unit location offers extra windows in the bedroom overlooking the golf course, not common in the standard lock off plan. Renovations include a remodeled kitchen, energy-efficient stainless steel appliances, new furnishings, and granite countertops. Bathrooms are appointed with custom showers and stylish vessel sinks. Additional upgrades include plantation shutters, crown molding, new fans, split A/C system, luxury vinyl and tile flooring throughout. Grand Champions features 2 pools and wonderful mature landscaping. Nearby are all of Wailea's resort amenities, including first-class restaurants, championship golf courses, tennis facilities, elite shopping opportunities, and miles of white sand beaches and ocean recreation. Finely appointed and being sold fully furnished. Listing agent is owner.

155 Wailea Ike Pl Unit 29, Kihei

Listing courtesy of Coldwell Banker Island Prop(S).

$750,000
1 Beds ⋅ 2 Baths ⋅ 410775 MLS ⋅ Fee Simple Tenure ⋅ Grand Champions BLDG.
Opportunity knocks at Grand Champions 122, offering an exceptional opportunity to own in the heart of Wailea at an unbeatable price point. Enjoy beautiful outer-island views toward Kaho'olawe and Molokini Crater from this ideally positioned residence. Location is everything, and this top-floor unit with high vaulted ceilings puts the best of Wailea within easy reach. For the tennis or pickleball enthusiast, the renowned Wailea Tennis Club is just a stone’s throw away, while the shops, dining, services, and everyday creature comforts of Wailea Town Center are right outside your front door. Wailea’s world-class beaches, championship golf courses, luxury resorts, shopping, dining, and coastal lifestyle are all nearby. Grand Champions is known for its lush tropical landscaping, convenient location, and resort-style atmosphere, with two swimming pool and spa areas located throughout the community. Whether you’re searching for a primary Maui residence, second home, or rental opportunity, Grand Champions 122 delivers a compelling combination of location, views, lifestyle, and value. At this price point, opportunities in Wailea are increasingly difficult to find. Grand Champions 122 will not last long. Wailea, Maui, Hawai'i… No Ka 'Oi!

155 Wailea Ike Pl Unit 122, Kihei

Listing courtesy of Coldwell Banker Island Prop(S).

$2,399,000
3 Beds ⋅ 3 Baths ⋅ 410693 MLS ⋅ Fee Simple Tenure
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-bedroom, 2.5-bath residence feels both refined and relaxed, with soaring vaulted open-beam ceilings, abundant natural light, dark bamboo flooring, mahogany doors and cabinetry, granite countertops, and plantation shutters throughout. The open-concept living area flows seamlessly through expansive sliding glass doors to a lush tropical backyard and patio, creating an inviting indoor-outdoor setting for alfresco dining, entertaining, or unwinding beneath the Maui sky. The well-appointed kitchen features stainless-steel appliances, generous storage, a pantry, and casual dining nook, while split-system air conditioning throughout provides year-round comfort. Upstairs, the entire level is devoted to the spacious primary suite—a private sanctuary complete with a sitting area, walk-in closet, ensuite bath, and its own lanai. Just moments from Wailea Kai’s dedicated community park and an easy stroll to world-renowned Keawakapu Beach, the best of Maui’s coastal lifestyle is right outside your door, with white sand, turquoise water, and unforgettable sunsets just minutes away. Wailea’s acclaimed dining, luxury shopping, championship golf, tennis, and resort amenities are also close at hand. This private Wailea residence offers a comfortable setting for enjoying the beauty and convenience of life in one of Maui’s most sought-after communities.

30 Waikai St, Kihei

Listing courtesy of Romvari Realty Ltd.

$1,850,000
2 Beds ⋅ 3 Baths ⋅ 410669 MLS ⋅ Fee Simple Tenure ⋅ Wailea Palms BLDG.
Welcome to Wailea Palms 2801, a beautifully updated and furnished 2-bedroom, 3-bath residence offering 1,559 square feet of unparalleled island living. One of the most private residences in the community, 2801 features three private lanais, creating wonderful indoor-outdoor living throughout the home. A rare feature of this unit is the ability to barbecue right off the lanai. Ocean views provide a beautiful backdrop for morning coffee, sunset dinners, or simply enjoying Maui’s year-round outdoor lifestyle. The thoughtfully updated interior features a beautifully appointed kitchen, inviting living and dining areas, and two generous bedroom suites offering privacy for owners and guests. Wailea Palms is a gated residential community known for its lush tropical grounds, ocean-view pool and spa, and peaceful setting. Ideally located near Wailea’s world-class beaches, golf, dining, shopping and resorts, Unit 2801 offers a rare combination of privacy, space and indoor-outdoor living in the heart of Wailea.

3150 Wailea Alanui Dr Unit 2801, Kihei

Listing courtesy of Coldwell Banker Island Prop(S).

$3,850,000
3 Beds ⋅ 4 Baths ⋅ 410561 MLS ⋅ Fee Simple Tenure ⋅ Hoolei BLDG.
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 Hibiscus layout—this spacious split-level townhome blends 3,076 sq.ft. of exquisitely refreshed interior space with approximately 700 sq.ft. of covered lanai for seamless indoor-outdoor living. Positioned in a coveted front-row location, you are steps away from Ho’olei’s world-class amenities, featuring a lagoon-style pool with a dramatic 19’ waterfall, swim-in grotto, dual spas, fitness facility, and poolside entertaining pavilion. Just moments from Wailea Beach, fine dining, championship golf, and shopping, this beautifully furnished residence offers exceptional privacy, a place to call home in Maui, alongside a stellar, proven rental track record.

24 Hoolei Cir Unit T-1, Kihei

Listing courtesy of Keller Williams Realty Maui-Ka.

$2,500,000
3 Beds ⋅ 3 Baths ⋅ 410525 MLS ⋅ Fee Simple Tenure
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 photovoltaic panels, brand-new luxury vinyl flooring and new baseboard throughout, a private pool, and an effortless flow make this the perfect expression of the Maui lifestyle. Minutes from the world-class dining, shopping, and championship golf of Wailea Resort, all within a serene, gated 34-acre community with lush tropical landscaping year-round. A rare single-level gem in one of South Maui’s most sought-after neighborhoods.

3111 Waiea Pl, Kihei

Listing courtesy of Maui Luxury Real Estate LLC.

$1,557,000
2 Beds ⋅ 2 Baths ⋅ 410487 MLS ⋅ Fee Simple Tenure ⋅ Wailea Palms BLDG.
Welcome to Wailea Palms 2703, FULLY FURNISHED and move-in ready, spectacular and renovated ground-floor 2 Bedroom, 2 Bath residence in one of Wailea's most sought after gated communities. Offering zero stairs from the parking area to the unit. 2703 combines effortless convenience with refined island living. Thoughtfully designed floor plan flows seamlessly through Fleetwood sliding glass doors to a large covered wrap around lanai with ocean views and lush tropical landscaping, perfect for indoor-outdoor living and entertaining. Recent upgrades include fully remodeled bathrooms (2025), travertine flooring, brand new fans and appliances throughout, custom cherry wood cabinetry, and handcrafted built-ins by Olivery Woodworking - including a custom breakfast nook, dining table, bathroom cabinetry, and custom glass and wood doors. A built-in Murphy bed in the second bedroom adds flexibility, allowing the space to function as either a guest suite or home office. Every detail has been designer curated, including designer furnishings, décor, accessories and kitchenware. Truly turn-key. Wailea Palms amenities include a spectacular OCEAN VIEW pool and spa, fitness center, BBQs, and beautifully landscaped grounds. Just moments from Wailea's world-class beaches, golf courses, luxury resorts, fine dining, The Shops at Wailea and the scenic Wailea Beach Path, this exceptional residence offers the privacy, quality, and lifestyle that make Wailea one of Maui's premier destinations. Call to schedule a showing!

3150 Wailea Alanui Dr Unit 2703, Kihei

Listing courtesy of Keller Williams Realty Maui-Ka.

$20,500,000
3 Beds ⋅ 4 Baths ⋅ 410482 MLS ⋅ Fee Simple Tenure
Welcome to the quintessential Maui oceanfront estate, ideally situated on Keawakapu Beach—widely regarded as one of Maui’s most beautiful stretches of sand. This timeless Hawaiian residence embraces its unrivaled setting with approximately 2,500 square feet of covered outdoor living space, perfectly suited for beachfront lounging and entertaining. Designed with architectural integrity and island sensibility, the home features traditional Dickey rooflines topped with black glazed tiles imported from Japan. A electronic gate opens into a private, walled compound that includes the main residence, a detached two-bedroom guest cottage (Ohana), a two-car garage with workshop, and a beautifully landscaped courtyard with a pool and spa. The single level main home offers soaring 16 foot ceilings in the great room with a working fireplace serving as the centerpiece, complemented by an open-concept kitchen and expansive glass walls that frame breathtaking ocean views while preserving privacy. The main residence includes three bedrooms and four bathrooms, all designed with ease of access and comfort in mind. The detached two-bedroom, one-bath Ohana is finished to the same high standard, ideal for visiting family or guests. Set on 0.8 acres, the estate flows seamlessly from lush lawn to the beach, where a protective lava rock point cradles the property and collects soft white sand along this dramatic, crescent-shaped shoreline—one of the largest and most coveted on the island. A rare opportunity to own a true legacy property on Maui’s finest beachfront. **Disclosure** Some pictures have been Virtually Re-Staged and noted.

3146 S Kihei Rd, Kihei

Listing courtesy of Hawaii Life (W).

$7,800,000
3 Beds ⋅ 4 Baths ⋅ 410468 MLS ⋅ Fee Simple Tenure
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 for elevated island living. Terraced landscaping and hand-set rock walls guide you toward the hilltop entrance, offering a dramatic first glimpse of the infinity pool as you arrive. Step through the substantial solid walnut wood pivot door, flanked by bilateral side windows that flood the entry with natural light. Inside, the open-concept kitchen, dining, and living areas flow seamlessly past disappearing Fleetwood doors to a spacious lanai anchored by an infinity pool and spa. Beyond, sweeping views stretch across West Maui, Lanai, Kahoolawe, and Molokini. The lanai wraps to the south into an entertainer's dream — a full bar and BBQ area complete with a hidden large-screen TV — while a pool bath with full sauna delivers a true resort-at-home experience. The chef's kitchen is outfitted with a premium Thermador appliance suite, shaker and flat-front cabinetry, and granite countertops, plus a built-in white wine cooler and a sleek, temperature-controlled red wine storage room. Rounding out the first floor: a two-car garage, a large laundry room, a modern half bath, and a primary suite with direct lanai access, smart shower, smart toilet, double vanity, and a private outdoor soaking tub. Ascend the dramatic floating staircase, set off by a sleek modern chandelier and stone accent walls, to discover a hidden office and an open den with lanai access leading to an outdoor gathering area centered on an elegant fire pit — all framed by more sweeping ocean views. Two additional bedrooms complete the second floor: a guest suite with ensuite bath and lanai access, and a second primary suite featuring lanai access, a walk-in closet, an oversized smart shower, and a top-filling soaking tub. Home is offered fully furnished and situated on the highest elevated lot in Wailea. Quality and luxury abound — your perfect Wailea oasis awaits.

22 Halapa Pl, Kihei

Listing courtesy of Hawaii Life (W).

$4,200,000
2 Beds ⋅ 2 Baths ⋅ 410442 MLS ⋅ Fee Simple Tenure ⋅ Wailea Beach Villas BLDG.
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 space. The thoughtfully designed floor plan features new appliances and an extended kitchen island with plenty of seating, making it ideal for everyday living and entertaining. Power sunshades throughout the home provide added comfort and convenience. Quaint ocean view from the lanai. Wailea Beach Villas is one of Wailea's premier beachfront communities, offering two swimming pools, a fitness center, beautifully maintained tropical grounds, direct access to Wailea Beach, and a convenient location within walking distance of The Shops at Wailea, restaurants, and nearby resorts. H102 is currently part of an active vacation rental program, making it an excellent option for those seeking a property with established rental history as well as a comfortable personal retreat.

3800 Wailea Alanui Blvd Unit H102, Kihei

Listing courtesy of Hawaii Life (W).

$1,295,000
2 Beds ⋅ 2 Baths ⋅ 410367 MLS ⋅ Fee Simple Tenure ⋅ Wailea Fairway Villas BLDG.
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 Maui sunsets from the comfort of your own home. Residents enjoy exceptional amenities, including a clubhouse with a fitness center, swimming pool, hot tub, barbecue area, outdoor dining space, and event room. Ideally located in the heart of Wailea, you're just minutes from five of South Maui's finest beaches, world-class golf, luxury shopping, award-winning restaurants, spas, and everything that makes Wailea one of Hawaii's most sought-after communities. Set on 12 acres of beautifully landscaped grounds, Wailea Fairway Villas offers the perfect blend of resort-style living and everyday comfort.

3950 Kalai Waa St Unit R102, Kihei

Listing courtesy of Coldwell Banker Island Prop-Ku.

$2,995,000
2 Beds ⋅ 2 Baths ⋅ 410363 MLS ⋅ Fee Simple Tenure ⋅ Wailea Elua Ii BLDG.
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 bedroom, 2 bathroom residence offers 1,363 square feet of interior living space with beautiful ocean views and the added privacy of bordering a lush greenbelt. Vaulted ceilings in the living room and guest bedroom create an open, airy feel, while large windows and sliding glass doors fill the home with natural light. Nearly every room enjoys views of the Pacific and surrounding tropical landscape. The spacious primary suite features its own private lanai, a generous walk in closet, and an additional storage room, providing exceptional functionality. The expansive main lanai borders the greenbelt and offers an inviting setting for outdoor dining, relaxing, and taking in Maui's sunsets. A washer and dryer are conveniently located within the residence, and central air conditioning provides added comfort. Offered furnished and move in ready, the residence presents an exceptional opportunity for a new owner to update and personalize the interiors while maximizing the value of its outstanding location, desirable floor plan, and ocean view setting. Wailea Elua offers direct access to Ulua Beach, two swimming pools, spas, a fitness pavilion, tennis court, gated entry, beautifully maintained grounds, and on-site security. Located just moments from championship golf courses, The Shops at Wailea, acclaimed restaurants, and the Wailea Beach Path, Unit 2010 is an exceptional opportunity to create your own island retreat in one of Maui's most sought after resort communities.

3600 Wailea Alanui Dr Unit 2010, Kihei

Listing courtesy of Island Sotheby's International Realty(W).

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