Wailea Homes with Fee Simple Land tenure

Welcome to Wailea, a stunning coastal paradise nestled on the southern shores of Maui, Hawaii. Known for its luxurious ambiance, pristine beaches, and breathtaking ocean views, Wailea is not just a destination; it’s a lifestyle. With its lush landscapes and year-round sunshine, this upscale community offers a perfect blend of relaxation and adventure, making it an ideal place to call home.

Wailea is renowned for its world-class resorts, championship golf courses, and exquisite dining options. Residents and visitors alike can indulge in an array of outdoor activities, from snorkeling in the crystal-clear waters of Wailea Beach to hiking along the scenic coastal trails. The neighborhood boasts a warm, inviting community atmosphere, where friendly faces and vibrant local culture come together to create a unique sense of belonging.

For those seeking to invest in their own slice of paradise, Wailea offers homes with fee simple land tenure, providing homeowners with full ownership of both the property and the land it sits on. This is a significant advantage, as it grants you the freedom to personalize your home and enjoy the benefits of true ownership in this idyllic setting.

Whether you’re looking for a luxurious oceanfront villa, a cozy townhome, or a spacious single-family residence, Wailea presents a diverse range of real estate options to suit every lifestyle. Embrace the allure of island living and discover why Wailea is considered one of Hawaii’s most coveted neighborhoods. With its stunning natural beauty and vibrant community spirit, you’ll find that Wailea is not just a place to live, but a place to thrive.

Newest Wailea Homes with Fee Simple Land tenure

$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).

$1,680,000

2 Beds ⋅ 2 Baths ⋅ 410361 MLS ⋅ Fee Simple Tenure ⋅ Keala O Wailea BLDG.

Discover one of Wailea's rarest offerings ; a beautifully appointed ground-floor residence that pairs effortless access with exceptional views. This stunning 2-bedroom condominium at Keala O Wailea offers a combination seldom found: the convenience of single-level living, breathtaking ocean views, and the privacy of one of the community's most desirable locations. Thoughtfully positioned in a quiet corner of the complex, this meticulously maintained home enjoys an expansive green lawn just beyond the lanai, making it an ideal retreat for pet owners and those who appreciate seamless indoor-outdoor living. The sense of privacy is remarkable, creating a peaceful sanctuary surrounded by lush tropical landscaping. Inside, every detail reflects quality and care. High-end luxury furnishings, sophisticated finishes, and several custom enhancements elevate the home well beyond the ordinary. The spacious, open-concept floor plan is filled with natural light and captures the beauty of Wailea from the main living areas, creating an inviting atmosphere for both everyday living and entertaining. Keala O Wailea is one of Wailea's premier luxury residential communities, ideally perched above the Wailea Blue Golf Course. This gated enclave offers an exceptional island lifestyle with resort-inspired amenities, including an elegant pool and spa, a beautifully appointed pavilion with an outdoor kitchen, and a spacious fitness center. Just moments away are Wailea's world-renowned beaches, championship golf courses, luxury shopping, acclaimed restaurants, scenic coastal paths, and the unparalleled natural beauty that defines South Maui. Whether you're searching for a full-time residence or an elegant island retreat, this exceptional home embodies the privacy, comfort, and refined island lifestyle that make Wailea one of Hawaii's most coveted places to call home.

67 Wailea Gateway Pl Unit 6-103, Kihei

Listing courtesy of Hawaii Life (W).

$4,795,000

3 Beds ⋅ 4 Baths ⋅ 410334 MLS ⋅ Fee Simple Tenure ⋅ Papali Wailea BLDG.

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 location, this exquisite residence is being offered for the first time since the original developer release. This single-level three bedroom and three-and-a-half baths provides the comfort and presence of a private home with the carefree and secure lock and leave benefits of a luxury condominium lifestyle. Sweeping ocean and outer-island views are complemented by Papali’s award winning design, contemporary architecture, and distinctive copper rooflines. Set on over ten acres of beautifully maintained tropical landscaping, Papali offers an exclusive sense of serenity with only two homes per acre providing privacy, tranquility, and a spacious sense of place just moments from Wailea’s pristine beaches, golf, dining, and shopping. Inside highlights include soaring vaulted ceilings with Alaskan Yellow Cedar beams, rich African mahogany millwork, limestone flooring, and a gourmet kitchen with premium granite surfaces. Flooded with natural light, expansive glass doors, and open generous lanai spaces for seamless indoor-outdoor living. Perfect for sunset gatherings and relaxed island evenings under the stars. A private garage, abundant storage, and dual entry points complete this rare and remarkable offering - furnished for your turn-key Maui lifestyle. Papali #17 isn’t just a home – it’s a legacy. Wailea’s most extraordinary offering.

3100 Wailea Alanui Dr Unit 17, Kihei

Listing courtesy of Coldwell Banker Island Prop(S).

$3,695,000

3 Beds ⋅ 3 Baths ⋅ 410261 MLS ⋅ Fee Simple Tenure ⋅ Makalii At Wailea BLDG.

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 expansive and unobstructed views. This gently lived in home has gorgeous finishes throughout with smooth tile floors extending in all directions. The chef’s kitchen is exquisite with high quality SubZero, Wolf, and Cove stainless appliances, beautiful quartz countertops, and handsome cabinetry. The generous living and dining area culminate with the dramatic 13 foot ceiling above the gliding glass doors leading to your peaceful lanai. The main level also includes a wonderful full bath and your secondary suite. Descending the striking contemporary staircase leads you to the ultimate privacy of your primary suite. There, you will find the retreat you’ve been dreaming of, with a large, private lanai offering incredible views and a spacious principal suite featuring generous closets and storage plus a huge ensuite bath with a luxury bathtub and oversized separate shower. Separate laundry room with quality Asko W/D. You will notice that all of the modern touches throughout are both elegant and functional for the way you live. The unique potential of the Casita is an outstanding feature for your visiting family and loved ones, and from the inner courtyard lanai, you ascend a staircase to the Casita Suite, where you will enjoy Majestic Haleakala views and yet another luxurious ensuite bath. Your one car garage means means more storage and vehicle protection year round and peace of mind during travel. This amazing recent community is everything you’ve been looking for in a Maui home with stunning pool area, workout facilities, and so much more. Steps from the Fairmont Kea Lani, a short stroll to Polo Beach and the Wailea Beachwalk, with all the world class beaches, restaurants, and shopping that the Wailea Resort has to offer at your fingertips, it’s time for you to discover the Magic of Makali’i.

208 Holomoana Way Unit 14B, Kihei

Listing courtesy of Hawaii Life (W).

$1,079,000

2 Beds ⋅ 2 Baths ⋅ 410253 MLS ⋅ Fee Simple Tenure ⋅ Wailea Fairway Villas BLDG.

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 breathtaking ocean, outer island, and golf course views with unforgettable year-round sunsets. This finely appointed 2-bedroom, 2-bath residence has been freshly painted from top to bottom and features a brand-new split A/C system. Offered fully furnished by the sellers, this move-in ready home allows you to begin enjoying the Wailea lifestyle from day one. The light-filled open floor plan flows seamlessly to a spacious covered lanai, creating the perfect setting for indoor-outdoor living. Wailea Fairway Villas offers a resort-style pool, spa, fitness center, BBQ area, and beautifully maintained tropical grounds, all just minutes from Wailea’s white sandy beaches, 3 championship golf courses, local eateries, luxury shopping, and world-class resorts. Whether you’re looking for a full-time residence, a vacation home, or simply a place to embrace the Maui lifestyle, S202 is a rare opportunity to own one of the community’s premier view residences.

3950 Kalai Waa St Unit S-202, Kihei

Listing courtesy of Coldwell Banker Island Prop(S).

$3,750,000

3 Beds ⋅ 3 Baths ⋅ 410226 MLS ⋅ Fee Simple Tenure

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-bedroom, 3-bath residence in Wailea Golf Estates offers a rare combination of privacy, elegance, and effortless island living. Relax and recharge with EV charging and the opportunity to add your own personal touches, making this a truly turnkey canvas for your Maui dream home. Architectural plans for a modern luxury home have been approved by the County of Maui, and are avaialble upon request. Designed for the quintessential indoor-outdoor lifestyle, the home's spacious interiors flow seamlessly to expansive lanais ideal for entertaining or quiet relaxation. Sweeping blue ocean vistas, neighbor island silhouettes, and brilliant Maui sunsets serve as your ever-changing backdrop, while lush tropical landscaping lends a serene, resort-like quality to every corner of the property. The thoughtfully designed floor plan offers generous living areas, a well-appointed kitchen, and comfortable bedrooms — two of which open directly to their own private lanais and offer panoramic views from their lanais. Whether hosting guests or savoring peaceful evenings at home, this property captures everything that makes Maui living so extraordinary. Just minutes from world-class beaches, championship golf, and fine dining.

3919 Waakaula Pl, Kihei

Listing courtesy of Century 21 Island Homes.

$1,575,000

2 Beds ⋅ 2 Baths ⋅ 410202 MLS ⋅ Fee Simple Tenure ⋅ Wailea Ekolu BLDG.

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 renovated (2025), 2 Bedroom, 2 bath unit! You are immediately drawn to the large, private lanai where stunning views await and are always available from the living, dining, and kitchen areas, as well as the primary bedroom. Your new kitchen has been tastefully updated with quartz countertops, mosaic tile backsplash, handsome cabinetry with undercab lighting, pendant lights with attractive palm ceiling fan, stainless appliances, and that wonderful ocean view. The living area features the ultimate Wailea Ekolu ocean view and the nice tile flooring that extends throughout the condo and lanai, beginning with the artistic tile inlay at the entry. There is a bamboo six-seat glass top dining table, and 3 Air-Conditioning units in the living areas provide cool comfort throughout your luxury vacation retreat. The primary bedroom offers ocean views, plenty of storage, and washer dryer in the ensuite bath, which also features the same striking quartz counters and wonderful cabinetry plus a large walk-in tiled shower. The secondary suite offers the same upgrades to the bath plus shower, lots of storage, and twin beds. Your elevated vantage point gives you commanding views of the sweeping Pacific and overlooks the upper village pool area, all while remaining wonderfully private from any of the neighboring units. Wailea Ekolu is a coveted location and a very in demand vacation rental community, so it is an excellent opportunity for both your enjoyment and also as an attractive place for your vacationing guests. Wireless internet is also provided and is covered by the maintenance fees. Whether you are looking for a full time residence, a vacation getaway, or a part time home with income potential when you are away, Wailea Ekolu #1706 allows you to have it all.

10 Wailea Ekolu Pl Unit 1706, Kihei

Listing courtesy of Hawaii Life (W).

$2,250,000

3 Beds ⋅ 3 Baths ⋅ 410198 MLS ⋅ Fee Simple Tenure ⋅ Kai Malu BLDG.

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/office with custom built cherry wood bookshelves, this is a beautifully appointed, freshly painted townhome. Overlooking Wailea Blue Golf Course, to the left, "the house of the sun" Haleakala and mesmerizing ocean views with crescent shaped Molokini and Kahoolawe in the fore front of the horizon view to its right. Emerald Green Golf views and Cobalt Blue ocean is the magic combination from both the living area on the first level and the primary bedroom. The en-suite bathroom has a spa-like feel with framed lotus tile and blue glass tile accents in the floor. Carpeted upstairs for lush living, and rich wood flooring through the living area, 22 photo voltaic panels that translates to an average electric bill of $25 per month, a wall safe, and EV charger. Pet friendly Kai Malu is a private gated enclave nestled at the heart of the Wailea community. The "hale" area with fitness center and infinity pool is the envy of Wailea. This home with a 2021 price tag is vacant, ready for its new owners.

363 Kai Malu Pl Unit 56B, Kihei

Listing courtesy of Keller Williams Realty Maui-Ka.

$3,895,000

3 Beds ⋅ 3 Baths ⋅ 410170 MLS ⋅ Fee Simple Tenure ⋅ La'i Loa BLDG.

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 4C (aka 30-201) offers epic ocean and golf course views and allows you to enjoy one of the closest proximities to the exclusive recreational center. Blending elegance and comfort, the spacious open concept layout features upgraded tile flooring which flows gracefully to the two covered lanais. The main lanai is perfect for year-round outdoor living and entertaining where you can savor unforgettable sunsets paired with great meals prepared on the built-in Coyote gas grill. The chef-inspired kitchen is appointed with Bosch stainless appliances, Fisher & Paykel double dishwasher, U-Line wine cooler, custom cabinetry, and a dramatic quartz waterfall island with bar seating and pendant lighting. The primary suite is a relaxing private sanctuary with its own lanai and privacy shade screen. This villa has been very gently lived in and further enhanced with upgrades such as Lutron programmable lighting, custom electronic blinds, Hansgrohe fixtures, Toto toilets, and a Rinnai on-demand hot water system. Custom furnishings designed specifically for this villa are also negotiable. A secure garage with an EV charging capability, large storage room and an additional assigned parking stall provide everyday convenience. Owners at La’i Loa enjoy an infinity edge pool with a lap lane, an oversized hot tub, and a modern fitness center all just steps away from your villa. Nearby are all of Wailea’s many resort amenities including some of the best beaches on Maui, elite shopping opportunities, first class restaurants, golf and tennis. Special properties like this rarely become available.

30 Kai Malu Dr Unit 201, Kihei

Listing courtesy of Coldwell Banker Island Prop(S).

$4,500,000

2 Beds ⋅ 2 Baths ⋅ 410129 MLS ⋅ Fee Simple Tenure ⋅ Wailea Point I Ii Iii BLDG.

Experience direct oceanfront, front-row living at Residence 1203 in Wailea Point, offering breathtaking, unobstructed ocean views, spectacular year-round sunsets, and front-row seats for seasonal whale watching—all from one of Maui's premier luxury communities. This spacious single-level, ground-floor residence is complemented by expansive covered and open-air lanais that create an exceptional indoor-outdoor lifestyle—perfect for outdoor dining, entertaining, whale watching, spectacular sunsets, and tranquil evenings under the stars with the soothing sound of the Pacific below. Enjoy effortless access to the lush tropical grounds while surrounded by exceptional privacy in one of Wailea Point's most coveted oceanfront settings. The thoughtfully designed floor plan features a spacious primary suite with a soaking tub, dual vanities, and Wailea Point's signature circular walk-in shower. A generously sized second bedroom with an en-suite bath provides comfortable accommodations for family and guests. A private single-car garage (Garage 1203G) is included in the sale. Wailea Point is widely regarded as one of Hawaii's finest luxury residential communities. Set on over 30 acres of lush tropical landscaping with fewer than five residences per acre, it offers an unmatched combination of privacy, beauty, and resort-style amenities. Residents enjoy 24-hour gated security, four swimming pools, spa pavilions, a 25-meter lap pool, fitness center, tennis and pickleball courts, barbecue areas, walking paths, and beautifully maintained gardens. The community is ideally situated between the Four Seasons Resort Maui and the Fairmont Kea Lani, with world-class beaches, championship golf, fine dining, and luxury shopping just moments away. In a 7/15/26 ruling, the Appeals Court changed the minimum rental period at Wailea Point BACK to 30 days. An Association Board of Directors Bulletin dated 7/22/26 states, “Consistent with the appellate court's decision, the minimum rental period is being administered as 30 consecutive days."

4000 Wailea Alanui Dr Unit 1203, Kihei

Listing courtesy of Wailea Point Realty, Inc..

$3,500,000

3 Beds ⋅ 2 Baths ⋅ 410112 MLS ⋅ Fee Simple Tenure

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 retreat pairs effortless accessibility and wide 36" doorways with the quiet polish of a private resort. Light filled interiors, soaring eight to twelve foot ceilings, and walls of Fleetwood glass open seamlessly to nearly a thousand square feet of lanai living. No expense spared with the choice of long lasting durable and as well as beautiful Monier tile roof, copper downspouts and gutters with French drains throughout. The finish level is exceptional, with large format Italian porcelain floors, a Poggenpohl kitchen with SubZero and Miele, and spa inspired baths featuring Toto washlets and Dornbracht fixtures. The primary suite opens directly to garden views, a shimmering saltwater pool and spa, and an outdoor shower wrapped in teak, while a thoughtful split bedroom layout offers guests true privacy. With owned photovoltaic, upgraded electrical, central air, remote sunshades, xeriscape landscaping, and copper landscape lighting, all just moments from Keawakapu Beach, Wailea's best shopping, and world class golf and tennis, this is turnkey Wailea living at its most refined and effortless. Outfitted with DWR (Design Within Reach) high-end furnishings, 39 Hoawaa is a turnkey residential experience.

39 Hoawaa Way, Kihei

Listing courtesy of Maui Luxury Real Estate LLC.

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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.