Refine Search
Sort by
1544 Halama St, Kihei
$7,770,000
4 Beds ⋅ 3 Baths ⋅ 411096 MLS ⋅ Fee Simple Tenure
Situated along one of South Maui’s most coveted oceanfront streets, 1544 Halama Street presents a rare opportunity to create an extraordinary luxury estate, with years of architectural planning, engineering, and permitting already completed. Following approximately five (5) + years of planning and design, this exceptional property offers approved architectural plans, structural engineering, building permits, and Special Management Area (SMA) approval, allowing the next owner to move forward without starting the lengthy entitlement process from scratch. A particularly compelling aspect of this opportunity is the approved renovation’s ability to preserve much of the existing residence’s oceanfront footprint. Given today’s increasingly restrictive shoreline setback requirements and SMA regulations, achieving a comparable design, scale, and proximity to the ocean could be extremely challenging, if not impossible, through a new permitting process. The thoughtfully designed plans envision a spectacular private oceanfront compound featuring expansive indoor-outdoor living spaces, a beautifully reimagined main residence, a swimming pool, and a separate two-story structure with an upstairs ohana and garage parking below. The design emphasizes a seamless connection between the home and the ocean, creating an exceptional setting for entertaining, relaxation, and enjoying the Maui lifestyle. With the architectural vision established and major approvals in place, the next owner can bring this remarkable estate to life while personalizing the interior finishes to reflect their own style and preferences. Opportunities to acquire oceanfront property with this level of planning, design, and permitting are exceptionally limited. At 1544 Halama Street, the value extends well beyond the land itself—it lies in the opportunity to create a legacy oceanfront estate in a location where comparable development potential may no longer be attainable.

1544 Halama St, Kihei

Listing courtesy of Keller Williams Realty Maui-Ki.

3800 Wailea Alanui Dr Unit F-302, Kihei
$7,495,000
3 Beds ⋅ 4 Baths ⋅ 411032 MLS ⋅ Fee Simple Tenure ⋅ Wailea Beach Villas BLDG.
The Spirit of Hawaii . . . . A timeless work of art blending retro charm with contemporary luxury. This extraordinary Villa brings character to a modern Island setting. The 2024 professionally decorated and renovated top-floor Villa is truly one of a kind at Wailea Beach Villas. This single-level technologically advanced smart residence is a rare expression of refined Maui living, combining sophisticated elegance with authentic Hawaiian soul. It features three spacious bedroom suites and three-and-a-half luxurious baths with automated window & lanai shades. The beautifully renovated interior is ideal for both relaxed island living and sophisticated entertaining. Designed for effortless indoor-outdoor living, the private turn-key Villa offers 3,568 sf total under roof living area and showcases breathtaking year-round ocean and sunset views. Amenities include an elevator, gated entry, manned security and private garage. A distinctive custom bar with a retro-inspired second refrigerator complements the newly renovated, fully stocked kitchen, which features refined finishes and premium Miele appliances, including a gas cooktop. Sophisticated, inviting, and unmistakably Maui, this exceptional residence captures the spirit of Hawaii in a way that is uniquely its own - a true one-of-one in the heart of the Wailea Resort. Its location is unsurpassed, situated on white sand beaches offering ocean activities, private beach lounge chairs and umbrellas along the renowned Wailea oceanfront pathway. Nearby, enjoy golf, tennis, pickleball, hiking, cycling, fine dining and the Shops at Wailea. You are invited to a private preview.

3800 Wailea Alanui Dr Unit F-302, Kihei

Listing courtesy of Compass-W.

4000 Wailea Alanui Dr Unit 1502, Kihei
$6,495,000
3 Beds ⋅ 4 Baths ⋅ 411236 MLS ⋅ Fee Simple Tenure ⋅ Wailea Point I Ii Iii BLDG.
THE OCEAN IS FRONT AND CENTER AT WAILEA POINT 1502. Perfectly positioned on a rare, elevated promontory directly above the revered Wailea Beach Walk, this front-row, immaculately maintained, 3 bedroom, 4 bathroom, two story 2,419 s.f. Residence 'lives large' encompassing 2 private ocean view lanais, totaling 544 s.f., and boasts commanding, Unobstructed Ocean, Outer Island, and Verdant Coastline Views.  You are as close to the ocean as Wailea allows. This furnished residence has been impeccably maintained and is offered in pristine condition.  The arrival sets the tone.  A light-filled Atrium, lush with tropical specimens, leads to the book-matched Hawaiian Koa wood front door, and beyond, the ever-changing coastal panorama. Upon entering there is a visceral feeling of serenity and tranquility amidst the understated quiet elegance of this spacious environment.  Floor-to-ceiling windows and the retractable glass slider invite the outdoors in, opening to entertaining lanai areas for enjoying alfresco dining and spectacular sunsets. This experience reaches into your senses and holds you there, suspended between sea and sky. The vaulted Clear Cedar ceilings & perimeter soffits with recessed copper-toned art lighting, tiled entry area & book-matched Koa doors throughout help to create a calm elegance and luminous foundation. Skylights & clear-story windows fill the interior with natural light. Culinary creativity has everything it requires in this delightful kitchen with granite counters, stainless steel appliances, Zebrawood cabinetry, and the spectacular views from the glass-on-glass corner kitchen window ensuring the experience of preparing a meal is as pleasurable as the meal itself.  The living and dining rooms are lined with a floor to ceiling mirrored wall expanding the ocean views from all directions. The upstairs primary suite is a sanctuary of quiet refinement.  Light-filled and serene, it features lofted ceilings, a walk-in closet with custom built-ins, an en-suite bathroom & spectacular 'Crow’s Nest' ocean views from the private lanai. A main level second primary bedroom with en-suite bathroom offers two private bathroom areas. There is also a lovely office/media room that can double as a guest suite with private bathroom. The wrap-around main level lanai offers alfresco dining, a BBQ & electric, privacy and hurricane rated sunshades. Set across 28 oceanfront acres bordered by two of Maui's finest beaches and adjacent to the Four Seasons and Fairmont Kea Lani Resorts, Wailea Point is a gated enclave in a luxury category of its own. Two resort-quality pool pavilions, a fully equipped fitness center, lighted tennis and pickleball courts, a cold plunge, multiple BBQ areas, and 24-hour roving security form a community that supports both the desire for privacy and the ease of a fully activated resort lifestyle. World-class dining, championship golf, fine shopping, hiking, and diving are all moments away. Front row, Elevated and Private is not a combination that comes available often. Wailea Point 1502 is a perfect blend of privacy, luxury and breathtaking natural beauty.

4000 Wailea Alanui Dr Unit 1502, Kihei

Listing courtesy of Maui Real Estate Advisors LLC.

3800 Wailea Alanui Blvd Unit PH-209, Kihei
$5,750,000
3 Beds ⋅ 3 Baths ⋅ 407859 MLS ⋅ Fee Simple Tenure ⋅ Wailea Beach Villas BLDG.
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 (configured as a 4th bedroom) offers 2,521 sq. ft. of SINGLE-LEVEL Luxury with refined finishes, open-concept design and seamless indoor-outdoor living. Secure elevator access to your penthouse. The gourmet kitchen features high-end appliances, custom cabinetry, and an inviting island that anchors the main living area. The generous covered lanai overlooks the tropical grounds with pool and ocean views, extending your living space for relaxing or entertaining. The primary suite with ocean views includes lanai access, a walk-in closet, and a spa-inspired bath, while 2 additional bedrooms and bathrooms plus the converted den offer excellent flexibility for guests or multi-generational living. Covered garage parking plus extra storage! Wailea Beach Villas provides exceptional resort-style amenities including gated security, direct beach access, two pools, hot tubs, fitness center, game room, business center, concierge services and lushly landscaped pathways throughout the property. Located steps from The Shops at Wailea, world-class dining, championship golf, and the Wailea Beach Path, the lifestyle here is unmatched. Penthouse 209 is offered Fully Furnished and ready for effortless living or rental use. A standout opportunity to own in one of Wailea’s most sought-after communities. Contact your Realtor® today for a private showing.

3800 Wailea Alanui Blvd Unit PH-209, Kihei

Listing courtesy of Keller Williams Realty Maui-Ka.

20 Makena Rd Unit 405, Kihei
$5,550,000
2 Beds ⋅ 2 Baths ⋅ 411247 MLS ⋅ Fee Simple Tenure ⋅ Polo Beach Club BLDG.
Never before offered on the market, Unit 405 is a true legacy property held by its original owner since construction. Positioned proudly in the coveted front row, front and center, this rare residence boasts the largest lanai layout in the entire community, delivering an unparalleled vantage point for South Maui's most spectacular sunsets, whale watching, and panoramic views stretching across the Pacific toward Molokini Crater and Kaho'olawe. Experience the ultimate blend of beauty and tranquility from this premier Polo Beach Club residence. Perfectly situated along the pristine, golden sands of Polo Beach, this elite oceanfront community offers an exceptional island lifestyle defined by meticulous tropical grounds and direct, private gated access to one of South Maui's most treasured beaches. Inside, the inviting 2-bedroom, 2-bathroom layout serves as a flawless canvas for coastal living. This residence perfectly transitions indoor comfort to an expansive, covered lanai where you can live to the rhythmic sounds of the ocean waves. Whether you are looking for a generational private retreat or an iconic investment property, unit 405 combines a world-class beachfront location with premium resort amenities-including a newly remodeled oceanfront

20 Makena Rd Unit 405, Kihei

Listing courtesy of Coldwell Banker Island Prop(S).

136 Manauea St Unit Unit 9, Kihei
$5,500,000
410497 MLS ⋅ Fee Simple Tenure
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 shoreline of Maluaka Beach and adjacent to the world-class Makena Golf & Beach Club, this exceptional community offers an unparalleled island lifestyle. Ownership at Maluaka Mauka includes coveted membership application rights to the private Makena Golf & Beach Club. Enjoy close proximity to Maluaka Beach, one of South Maui's most beautiful swimming and snorkeling beaches, as well as convenient access to the Club's beachfront restaurant and bar, ocean pursuits activities, pools, fitness center, sports fields, and other amenities. Golf cart access provides a seamless connection to the Club's championship golf course and racquet sports complex. Offering privacy, open space, and an exceptional location, Maluaka Mauka presents a rare opportunity to build your dream home in one of Maui's most sought-after coastal communities. Unit 9 is one of the most desirable homesites within the exclusive Maluaka Mauka, ideally positioned along the perimeter of the community. Overlooking the amenities of the Makena Golf & Beach Club, this premier homesite is bordered on one side by a dedicated cultural preserve, providing a rare sense of openness and a protected natural setting. This unique location offers an extraordinary opportunity to create an island retreat while enjoying convenient access to Maluaka Beach and the world-class lifestyle amenities that make Makena one of Maui's most sought-after destinations. Disclaimer: Pricing reflects individual homesite offerings within a master-planned community. All renderings, photography, floor plans, site plans, maps, dimensions, specifications, amenities, and other marketing materials are conceptual in nature and are provided for illustrative purposes only. They are subject to change without notice and should not be relied upon as a representation of the final product. Makena Golf & Beach Club Membership Disclaimer: Membership rights and privileges are subject to application and approval by Makena Golf & Beach Club, including completion and satisfactory approval of the Club’s required background screening process. Membership is not guaranteed and is subject to the Club’s then-current membership requirements, policies, and approval procedures.

136 Manauea St Unit Unit 9, Kihei

Listing courtesy of Discovery Makena Realty LLC.

3800 Wailea Alanui Blvd Unit PH511, Kihei
$5,395,000
2 Beds ⋅ 2 Baths ⋅ 407499 MLS ⋅ Fee Simple Tenure ⋅ Wailea Beach Villas BLDG.
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 2,000 square feet of thoughtfully designed indoor and outdoor living space, seamlessly blending contemporary elegance with relaxed island sophistication. Perched approximately 100 feet above the Pacific Ocean, the villa showcases panoramic views of Wailea Beach, the islands of Kaho?olawe, Molokini, and Makena's Pu?u Olai. The open-concept great room, finished with travertine flooring, extends onto a spacious partially covered lanai ideal for year-round indoor/outdoor living and entertaining. The primary suite offers a serene retreat with exceptional privacy. The second bedroom is furnished with two twin beds, and an additional room features a queen bed, allowing the villa to comfortably accommodate up to six guests. The gourmet kitchen combines granite and stainless-steel countertops with ample cabinetry and premium appliances, including Fisher & Paykel refrigerator and freezer (2025) and Bosch dishwasher (2024). It is also fully equipped with an array of convenient small appliances and gadgets, making daily living effortless. Additional conveniences include a new central air conditioning system (2022), new lanai furniture & carpet (2024), electronic blackout shades (2021), SimpliSafe smart water sensors (2025), and a full-size GE washer and dryer. Zoned for hotel/resort use, this elegantly furnished villa is currently operated as a short-term rental and is ready for immediate enjoyment or income potential. Projected rental income for 2026 is $244,000. Wailea Beach Villas is the newest oceanfront luxury gated community located in the heart of the world-renowned Wailea Resort, positioned directly in front of The Shops at Wailea and between the Grand Wailea and Marriott hotels. There are 99 luxury residences situated across 10.7 acres of beautifully landscaped tropical grounds. Amenities include an oceanfront swimming pool, a family pool, a fitness center, conference facilities, and a game room with a pool table, along with 24-hour gated security. Just steps from pristine beaches, upscale dining, designer shopping, and championship golf, this remarkable luxury penthouse villa is offered at an exceptional value and presents a rare opportunity to own in one of Maui’s most prestigious beachfront communities—an opportunity not to be missed.

3800 Wailea Alanui Blvd Unit PH511, Kihei

Listing courtesy of Coldwell Banker Island Prop-Ku.

81 Makakehau St Unit Apt H-2, Kihei
$4,999,999
3 Beds ⋅ 4 Baths ⋅ 408222 MLS ⋅ Fee Simple Tenure ⋅ Hoolei BLDG.
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 world-class resorts, fine dining, luxury shopping, championship golf courses, and Maui's best beaches. The Villa features 3 bedrooms and 3.5 bathrooms, in a two-story townhome-style, encompassing 2,426 square feet. There is an additional 596 square feet of covered lanais across two levels. Each bedroom includes a private ensuite bath, offering comfort and privacy for owners and guests alike. Thoughtful design elements include a private elevator, an attached garage, a covered carport, and an outdoor storage closet. Floor-to-ceiling sliding glass doors and retractable screens open almost 30 feet onto the expansive lanai, embracing Maui's indoor/outdoor lifestyle. The lanai is ideal for entertaining and is equipped with a Wolf 36" grill, a Sub-Zero under-counter refrigerator, and custom cabinets. The Villa features polished travertine floors, recessed lighting, high tray ceilings, surround sound, a security system, and a 2-zone central air conditioning system. The Chef's kitchen includes premium appliances by Sub-Zero, Wolf, Thermador, and Bosch. A touch of elegance is added with the Snaidero Italian custom cabinetry. You can enjoy ocean views from high above the resort pool. Ho'olei's amenities include a lagoon-style pool with cascading waterfalls and grottos, a sandy beach entry, two hot tubs, a massage cabana, an outdoor kitchen with covered pavilion, and a fully equipped, air-conditioned fitness center with sauna, locker rooms, and showers. Offered fully furnished, the Villa is truly turn-key & has been meticulously maintained. The property is hotel-zoned, allowing use as a short-term vacation rental, private residence, or a combination of both. Successfully operated as a vacation rental since 2007, the Villa has received over 150 five-star reviews. The owner is willing to continue marketing the property or assist with a smooth transition to new management. This remarkable Ho'olei Villa presents a rare opportunity to own a luxury, hotel-zoned home in paradise.

81 Makakehau St Unit Apt H-2, Kihei

Listing courtesy of Coldwell Banker Island Prop(S).

3100 Wailea Alanui Dr Unit 17, Kihei
$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).

1210 Uluniu Rd Unit Unit 1, Kihei
$4,750,000
2 Beds ⋅ 2 Baths ⋅ 410959 MLS ⋅ Fee Simple Tenure
Old Kihei, the way it used to be. Beneath huge old mango trees, this gracious 1938 beach house recalls an earlier Hawai'i of open lanais, trade winds and evenings spent watching the sun sink into the Pacific. Completely remodeled in 2006, the 2BR/2BA, 1,156 SF home retains its Territorial-era character with soaring gables and post & pier construction, while an airy great room and travertine floors bring it comfortably into the present. A 252 SF covered lanai spans the entire ocean side of the home—made for morning coffee, shared meals and year-round sunsets, from open ocean to Lana'i, with whales offshore in season. Beyond the yard, State-owned open land dotted with coconut palms leads toward a natural beach approximately 170' away, without a seawall or revetment. Honu have nested directly in front, and groups regularly come ashore nearby at sunset. Separate 2-car garage & washhouse (laundry.) Beach access next door, Azeka Makai approximately 400' away, and much of everyday Kihei within walking distance. Tennis, pickleball and County pool nearby. Many homes try to capture old Hawai'i. This one has been here all along. This is Unit 1 of a 2-unit Land Condo-Adjacent 6,495 SF CPR Unit 2 also available (Vacant Land MLS #410958; $250K discount with purchase of both.)

1210 Uluniu Rd Unit Unit 1, Kihei

Listing courtesy of Hawaiian Voyage Realty.

4000 Wailea Alanui Dr Unit 2802, Kihei
$4,750,000
2 Beds ⋅ 2 Baths ⋅ 407132 MLS ⋅ Fee Simple Tenure ⋅ Wailea Point I Ii Iii BLDG.
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 iconic Molokini Island and stretching from the South Maui coastline to Lanai Island. This upper floor plan features soaring ceilings and an open, airy design. The elegant mitered glass bay windows majestically frame the already stunning vistas. The kitchen and bathrooms have been beautifully renovated with modern finishes, blending elegance and comfort. A loft (estimated at 250 gross sq. ft.) has been added, providing a separate, third sleeping area, den or play room. Garage 2802G is included (CPR 76). Wailea Point was developed to be the finest residential condominium in Hawaii - and many believe it is just that. It features exceptional quality construction, very low density (just over 4 units per acre), garden environment, low-rise buildings, 24-hour gated & roving security patrol, two outstanding pool pavilions with 4 pools (including a 25-meter lap pool), 2 whirlpool spas, full kitchens, lighted tennis court, 2 pickleball courts (1 lighted), a superbly equipped, air conditioned fitness gym, barbeque areas, fruit & herb gardens, ample parking - and it’s a golf-cart friendly property. Enjoy the Four Seasons and Fairmont Kea Lani Hotels as immediate neighbors (the Grand Wailea 1 property away) and all the 5-star services they offer. 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 2802, Kihei

Listing courtesy of Wailea Point Realty, Inc..

3943 Wailea Ekolu Pl, Kihei
$4,495,000
3 Beds ⋅ 4 Baths ⋅ 408559 MLS ⋅ Fee Simple Tenure
3943 Wailea Ekolu is one of Wailea Golf Estates' most distinctive ocean-view Residences, offering Panoramic Ocean, Outer-Island & Mountain Views, Estate-Scale Living, Timeless Architectural Character, and a Premier Golf-Frontage Setting. Encompassing approximately 4,355 square feet, this expansive residence features 3 bedrooms, an office/den, 4 full bathrooms, a spacious great room, and an additional living room that opens seamlessly to the pool and outdoor entertaining area. Designed with enduring craftsmanship, generous proportions, and a grand sense of arrival, the home showcases architectural details rarely found in today's newer luxury residences. From the moment you enter, arched mahogany-and-glass entry doors accented with African Wenge welcome you into a dramatic curved vestibule, where rounded plaster walls, rich mahogany millwork, and a grand staircase immediately reveal the craftsmanship and architectural character that define this remarkable home. Two en-suite bedrooms located on the ground floor each enjoys its own outdoor space—ideal should you want to have SINGLE FLOOR-PLAN LIVING. Upstairs, a PRIVATE SANCTUARY awaits: the approx. 1,581 sq. ft. primary bedroom suite and den offer exceptional PRIVACY and unparalleled OCEAN AND OUTER ISLAND VIEWS WITH WRAP AROUND LANAIS, along with impressive Haleakala vistas that shift beautifully with the light. The generous kitchen opens to a bright great room with SLIDING WALLS OF GLASS on two sides—inviting lovely cross-ventilation and framing views to the sparkling PACIFIC OCEAN. The formal living room offers a warm focal fireplace, natural cedar ceiling, and a recessed art niche. Expansive sliders from the great room and living room open to an OCEAN VIEW POOL AND SPA with a SPACIOUS TILED SUN DECK, made for sunset lounging and DINING AL FRESCO UNDER THE STARS. The layout is wonderfully open, yet intentionally defined, with sight lines that draw you toward the outdoors and the enchanting views beyond. This home is a LUMINOUS LIGHT-FILLED CANVAS—ready for your vision: an extraordinary opportunity to re-imagine and elevate a residence of substance, scale, & soul. Set within the prestigious gated Wailea Golf Estates, backing to the 11th fairway of the Wailea Blue Course, and moments to Wailea’s world-class beaches, dining, shopping, golf, tennis, water sports, and spas.

3943 Wailea Ekolu Pl, Kihei

Listing courtesy of Maui Real Estate Advisors LLC.

119 E Welakahao Rd, Kihei
$4,390,300
408100 MLS ⋅ Fee Simple Tenure
** Sale includes MLS #s 408092, 408093, 408094, 408095, 408096, 408097, 408098, 408099, 408100, 408101, 408143, 408102, 408103, 408104, 408106 & 408107 ** Rare opportunity to acquire a multi-site land portfolio spanning Wailuku, Kihei, and Makawao—three of Maui’s most sought-after and growing regions. The portfolio consists of 16 parcels totaling approximately 272.055 acres, offering significant scale, diverse topography, and strategic locations suitable for investment, master planning, or phased development. Properties are offered for sale exclusively as a single portfolio. Any individual parcel pricing shown is for MLS compliance purposes only and does not reflect standalone availability or value. The portfolio purchase price is $48,000,000.00

119 E Welakahao Rd, Kihei

Listing courtesy of Commercial Prop of Maui LLC.

3377 E Lani Ikena Way, Kihei
$4,295,000
4 Beds ⋅ 5 Baths ⋅ 411289 MLS ⋅ Fee Simple Tenure
Intentionally Designed. Exceptionally Crafted. Distinctively Wailea. Introducing an extraordinary custom residence in the coveted Wailea Pualani neighborhood, where thoughtful architecture, exquisite craftsmanship, and an uncompromising attention to detail come together in a home of remarkable distinction. Built in 2021 by renowned local builder Artistic Builders, this meticulously maintained 3,513-square-foot luxury home is offered for the first time, presenting a rare opportunity to experience newer construction in one of South Maui's most desirable communities. Conceived as a personal sanctuary rather than a speculative build, every element was carefully considered—from the flow of the interiors and the framing of ocean views, to the selection of materials and the seamless connection between indoor and outdoor living. An exceptional interior lot provides privacy, tranquility, and beautiful ocean vistas without the intrusion of road views or traffic noise. Expansive Fleetwood sliding glass doors dissolve the boundaries between indoors and out, creating an effortless transition between sophisticated interiors and Wailea's celebrated outdoor lifestyle. The main-level primary suite is a retreat unto itself, opening directly to the pool and spa. A second primary suite upstairs, complete with a separate exterior entrance and access to the pool below, provides flexibility for family and guests. Four ensuite bedrooms provide beautifully appointed accommodations, complemented by a dedicated office with potential for a fifth bedroom and a separate media room designed for gathering, entertaining, or simply unwinding. Beyond the pool, an expansive, fully usable and level lawn offers something increasingly rare in Wailea: generous, usable green space for recreation, entertaining, or quiet moments outdoors. From the front lanai, year-round sunsets paint the Pacific horizon, while spectacular fireworks displays from the nearby Grand Wailea illuminate the evening sky on special occasions. Throughout the residence, the quality of construction reveals itself in both the extraordinary and the understated. Museum-quality Level 5 wall finishes, handcrafted walnut stair treads, custom walnut-inlaid entry doors, fossilized bamboo flooring, imported designer tile, quartz countertops and backsplashes, and bespoke glass artistry by Makai Glass reflect a level of personalization seldom found in today's market. A gourmet kitchen appointed with premium Sub-Zero and Wolf appliances complements the home's sophisticated functionality. Additional enhancements include a Halo 5 whole-house water filtration system and professionally installed UniFi networking for seamless connectivity. Offered fully furnished with a curated selection of Restoration Hardware and Arteriors pieces, the residence offers a refined yet welcoming expression of contemporary island luxury. More than a collection of exceptional finishes, this Wailea residence embodies the essence of elevated Maui living. A rare opportunity to own a truly custom Wailea residence, created with intention, crafted with quality, and offered with pride for the very first time.

3377 E Lani Ikena Way, Kihei

Listing courtesy of The Agency Maui.

3870 Wailea Ekolu Pl, Kihei
$4,250,000
3 Beds ⋅ 4 Baths ⋅ 411166 MLS ⋅ Fee Simple Tenure
3870 Wailea Ekolu Pl. presents a rare opportunity to own a luxury ocean-view home in Wailea Golf Estates, one of South Maui’s premier gated communities within the prestigious Wailea Resort. Positioned on an exceptional lot overlooking the ocean, this 3-bedroom, 3.5-bath residence captures panoramic views of Kahoolawe, Lanai, Molokai, and Molokini. Designed to maximize its breathtaking setting, the home features a functional floor plan, ensuite bathrooms in every bedroom, and seamless indoor-outdoor living. Enjoy Maui’s spectacular sunsets and seasonal whale watching from the spacious entertaining lanai, private swimming pool, and spa.The gated Wailea Golf Estates neighborhood is set among the scenic fairways of the Wailea Blue Golf Course, offering a desirable setting within one of Maui’s most sought-after resort communities. Ideally located just minutes from South Maui’s beautiful beaches, including Keawakapu Beach and Wailea Beach, the property also offers convenient access to championship golf courses, fine dining, luxury resorts, and upscale shopping at The Shops at Wailea. Whether seeking a primary residence or a private island retreat, 3870 Wailea Ekolu Pl. offers exceptional ocean-view living and the opportunity to enjoy the best of the Wailea lifestyle.

3870 Wailea Ekolu Pl, Kihei

Listing courtesy of Hawaii Life (W).

3800 Wailea Alanui Blvd Unit H102, Kihei
$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).

21 Kiloa St Unit O-4, Kihei
$4,195,000
3 Beds ⋅ 4 Baths ⋅ 408839 MLS ⋅ Fee Simple Tenure ⋅ Hoolei BLDG.
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 and is offered tastefully furnished, totally turnkey, and is active and successful in the Grand Wailea's exclusive vacation rental program. The Plumeria floor plan enjoys the widest lanai and forward most position of the building, enhancing privacy and extending the living area. This villa has new upgraded flooring in the bedrooms, a chef's kitchen with Wolf and Sub Zero appliances, a built in BBQ and fridge on the lanai, attached garage, private elevator, and so much more. Pocketing Fleetwood glass sliders blend the indoors with the outdoors, making a perfect space for entertaining your family and guests. The Ho'olei property offers a resort style pool and spas, with a state of the art workout facility and saunas. Ho'olei is gated with 24hr security and lush landscaping that gives you a sense of place here in Hawai'i. Owners are eligible for the Kulana Club with the Grand Wailea, allowing them rental management, shuttle service, on-site front desk and concierge, as well as a myriad of discounts and perks. The Wailea Resort offers some of the finest dining, shopping, golf, tennis, beaches, sunny days and views in the world!

21 Kiloa St Unit O-4, Kihei

Listing courtesy of Hawaii Life (W).

4000 Wailea Alanui Dr Unit 2904, Kihei
$4,195,000
2 Beds ⋅ 2 Baths ⋅ 408086 MLS ⋅ Fee Simple Tenure ⋅ Wailea Point I Ii Iii BLDG.
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 enclave's luxury and casual sophistication marries the divine setting with dramatic ocean views. Enjoy the premier Maui lifestyle in this private, spacious, fully furnished 2-bedroom, 2-bath residence in beautiful Wailea Point. High ceilings, huge picture windows, and beautiful finishes create the perfect setting for comfortable living and memorable entertaining that flows from spacious interiors to oceanview lanais. The spacious living room features large windows that let in plenty of natural light and offer panoramic views of the beach and ocean. Brand new window installation just completed, featuring a beautiful mitered glass bay window with custom automatic roll-down shades. The extraordinary, panoramic views look from the surf and sand of Polo Beach, across the ocean to the islands of Lanai, Kahoolawe, & Molokini, down the coast to Makena, and up to the summit of Haleakala. The kitchen features exceptionally fine Koa cabinets and high-quality appliances, including an oven, microwave, refrigerator/freezer, dishwasher, and ample cabinet space. The covered lanai is the perfect spot to savor a cup of coffee in the morning, enjoy the sunrise, or barbecue in the evening while taking in the expansive ocean views, sunsets, whales, dolphins, and seabirds. Wailea Point is a low-density 26-acre oceanfront property with impeccably landscaped common areas and top-quality amenities. 24-hour security, three swimming pools, a lap pool, two spas, BBQ pavilions, a fully equipped fitness center, lighted tennis, paddle tennis, and pickleball courts. Wailea Point is conveniently located between Wailea Beach and Polo Beach.

4000 Wailea Alanui Dr Unit 2904, Kihei

Listing courtesy of Coldwell Banker Island Prop(P).

21 Ualei Pl Unit 1, Kihei
$4,000,000
403676 MLS ⋅ Fee Simple Tenure
There is only one undeveloped lot remaining in the prestigious gated enclave of One Palauea Bay, so if you want to build in one of the best neighborhoods in Maui this is your last chance. 21 Ualei Place offers over 1.8 acres of land and a generous building envelope that allows for a luxury home and a separate cottage. It is, quite simply, one of the last chances to create something extraordinary in Makena within easy walking distance of the island’s best beaches and Wailea's resort amenities. Imagine waking each morning steps from Palauea Beach and Polo Beach, with the Wailea Beach Path and Fairmont Kea Lani just across the street. Fine dining, boutique shopping, and world-class golf are minutes away, yet privacy and serenity remain uncompromised. In a world where time is the ultimate luxury, opportunities like this do not wait. Once this lot is gone, there will never again be another parcel of this size in this location within this exclusive community. If you have been waiting for the perfect moment to create your Maui legacy, this is it.

21 Ualei Pl Unit 1, Kihei

Listing courtesy of The Maui Real Estate Team Inc.

4000 Wailea Alanui Dr Unit 2502, Kihei
$4,000,000
3 Beds ⋅ 4 Baths ⋅ 401515 MLS ⋅ Fee Simple Tenure ⋅ Wailea Point I Ii Iii BLDG.
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 plan located on the top 2 floors of a 4-story building; 2 levels, 3 bedrooms, 4 bathrooms. The location is a “10”, affording spectacular ocean views. The vaulted ceilings are a bonus, and new windows were installed in 2022, including the gorgeous mitered glass bay window that makes the ocean view from the living room simply POP! Facing west, 180-degree ocean views, year-round sunsets, and whales galore! The entire upstairs is a master suite with full bath & soaking tub, and its own private, 144 sq. ft. “crow’s nest" lanai with stunning views. Original condition except for the beautiful new windows. Unfurnished. Wailea Point was built to be the finest residential condominium in all of Hawaii - and many believe it is just that. Built in the late 1980's, it stole the show at the 1986 Parade of Homes, a competition sponsored by the Building Industry Association of Hawaii. It also won a national award from Sunset Magazine for best use of glass - and the sellers have improved on that by replacing windows, and installing the awesome "mitered glass bay window" in the living room. Aside from its World Class location, Wailea Point boasts ultra-high quality design & construction, very low density (just over 4 units per acre), low rise structures in a magnificent, garden environment. 24-hour roving & gated security; 2 elaborate pool pavilions with kitchens & barbecues; 4 pools (including a 2-lane, 25-meter lap pool); 2 whirlpool spas; lighted tennis & pickleball courts; superb fitness gym; extensive fruit & herb gardens; ample parking; and it's golf cart friendly! Enjoy the Four Seasons and Fairmont Kea Lani resorts as immediate neighbors, plus the Grand Wailea a short walk away, and all the 5-star restaurants & other services they offer. Well run AOAO. 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 2502, Kihei

Listing courtesy of Wailea Point Realty, Inc..

4850 Makena Alanui Rd Unit C106, Kihei
$3,950,000
2 Beds ⋅ 2 Baths ⋅ 407882 MLS ⋅ Fee Simple Tenure ⋅ Makena Surf BLDG.
Enjoy breathtaking unobstructed ocean, neighbor island, and sunset views from the living area, the kitchen, and the spacious lanai of this extra-large, elegantly renovated, two-bedroom, two-bath Makena Surf condo! This 1,600 square foot condo feels even larger thanks to the high ceilings, and central air-conditioning and the C-building's concrete construction provides its occupants with a comfortable, quiet place to unwind. This wonderful unit is perfectly perched on the top of the hill overlooking Po'olenalena Beach. Occupants enjoy additional privacy thanks to the u'lua heiau (fishing shrine) thought to be one of the landmarks directing ancient Hawaiians to one of the best fishing spots. No one is permitted to enter this area, which ensures maximum privacy and a sense of calm and tranquility. The lanai was beautifully expanded, and Fleetwood sliding doors and screens - flush to the floor - were installed, which created an ideal sense of, and setting for, indoor-outdoor living! Other thoughtful enhancements include a water filtering system, new appliances, and a keypad entry system. During whale season, one can watch the whales from the living area, kitchen, and the spacious lanai! Onsite amenities include two beautiful pools and pool areas (both of which were completely and beautifully renovated), pickleball, tennis courts, a fitness center, several BBQs, herb gardens, a management office, and gated access. This wonderful complex offers both peace and privacy, while still being only minutes from world-class golf, dining, and shopping. A few art pieces are excluded from the sale. Please contact your favorite Realtor to schedule a showing. HOTEL ZONING!

4850 Makena Alanui Rd Unit C106, Kihei

Listing courtesy of Hawaii Life (W).

78 Kai Malu Dr Unit 101 (14A), Kihei
$3,878,000
3 Beds ⋅ 3 Baths ⋅ 409909 MLS ⋅ Fee Simple Tenure ⋅ La'i Loa BLDG.
La'i Loa: Where Elevated Design Meets the Spirit of Wailea PRIVATE SHOWINGS AVAILABLE. Some homes have a view. This one makes the view part of daily life. From its elevated position at La'i Loa, the Pacific stretches to the horizon, with sweeping ocean vistas, neighboring islands, and Maui's legendary sunsets. Built in 2023, this ground-floor 3-bedroom, 3-bath residence offers 1,742 square feet of thoughtfully designed living space and a rare 424-square-foot lanai that extends the home outdoors. Trade winds, natural light, and an easy indoor-outdoor flow define the Wailea lifestyle here. Inside, every detail reflects quality and craftsmanship. Approximately $1 million has been invested in furnishings, artwork, lighting, and custom appointments, including hand-painted Italian wall coverings, rare Maya Romanoff wallpaper, hand-blown glass fixtures, and custom Italian furnishings. It feels more like a private gallery than a condominium. The gourmet kitchen features premium appliances and refined finishes for everyday living and entertaining. Motorized shades, smart-home compatibility, and integrated technology add modern convenience without compromising the design. On the lanai, an outdoor grilling area sets the stage for sunset dinners, morning coffee over the ocean, or evenings with friends. The setting is one of the most private in the community, surrounded by mature Monkey Pod trees and lush tropical landscaping for a serene, treehouse-like feel, with minimal through-traffic. La'i Loa has become one of Wailea's most coveted addresses. Each boutique building holds just five residences, with secured access and a private garage. Residents enjoy an infinity-edge pool, fitness center, and clubhouse within beautifully maintained grounds. Whether you want a primary residence with single-level living, a lock-and-leave second home, or a luxury investment with nearly new construction and strong long-term rental appeal, this home delivers. Offered fully furnished, with most furnishings, artwork, and designer pieces included, the next owner can step right into a lifestyle already beautifully curated. New construction. Boutique exclusivity. World-class interior design. Expansive ocean views. One of the most sought-after locations on Maui. This is more than a home. It is a front-row seat to everything that makes Wailea extraordinary. ALL FURNISHINGS INCLUDED IN THE SALES PRICE EXCEPT A FEW PERSONAL ITEMS.

78 Kai Malu Dr Unit 101 (14A), Kihei

Listing courtesy of Keller Williams Realty Maui-Ka.

3378 E Lani Ikena Way, Kihei
$3,870,000
4 Beds ⋅ 5 Baths ⋅ 408523 MLS ⋅ Fee Simple Tenure
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 locally inspired textures. Open-concept great room features panoramic ocean views, floor-to-ceiling glass, hardwood floors, and natural stone. Chef’s kitchen with waterfall stone island, premium appliances, and custom cabinetry. Luxurious bedroom suites offer spa-style baths, private lanais, and ocean or garden views. Resort-style outdoor living includes a lap pool, spa, Baja shelf, and tropical landscaping. Sustainable features include solar, smart home automation, and energy-efficient systems. Prime Wailea location near world-class beaches, golf, dining, and luxury resorts. One of the listing agents is the seller.

3378 E Lani Ikena Way, Kihei

Listing courtesy of Coldwell Banker Island Prop-Ku.

24 Hoolei Cir Unit T-1, Kihei
$3,650,000
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.

4955 Makena Rd Unit D302, Kihei
$3,599,000
4 Beds ⋅ 4 Baths ⋅ 411173 MLS ⋅ Fee Simple Tenure ⋅ Na Hale O Makena BLDG.
EXCEPTIONAL LUXURY, EXTRAORDINARY VIEWS, AND ROOM FOR EVERYONE! Welcome to Na Hale O Makena D302, a beautifully appointed, expansive 4-bedroom, 3.5-bath luxury condominium offering the space, comfort, and privacy of a gracious island residence, complemented by some of South Maui's most breathtaking ocean views. Imagine gathering family and friends for unforgettable Maui experiences, with generous accommodations that can comfortably host a large group. Whether you're looking for an extraordinary family vacation home, a multigenerational island retreat, or a private corporate getaway, D302 offers the flexibility and spaciousness to bring everyone together without sacrificing personal space. The magnificent ocean panorama takes center stage, with unobstructed views of Molokini, Kaho?olawe, spectacular year-round sunsets, and seasonal whale watching. From the rear bedroom, enjoy a peaceful view of majestic Haleakala. These are the views people dream of when they imagine owning a home in Maui. Inside, you'll discover elegant marble tile flooring, granite countertops, a beautifully designed Snaidero kitchen with premium Gaggenau and Bosch appliances, and thoughtfully furnished living spaces. An additional upstairs living area provides a wonderful second gathering space, ideal for entertaining, relaxing, or simply giving everyone room to spread out. Offered fully furnished, this residence is ready for you to begin enjoying the Maui lifestyle. Set on approximately six beautifully maintained acres with just 40 exclusive residences, Na Hale O Makena offers an intimate, private setting rarely found in condominium living. Residents enjoy a swimming pool, spa, fitness center, and the peace of mind that comes with a gated community. Vacation rentals are prohibited, helping preserve the residential atmosphere and tranquility that make this property so special. Located just minutes south of Wailea's championship golf courses, world-class resorts, fine dining, luxury shopping, and spectacular beaches, you'll enjoy convenient access to South Maui's finest amenities while returning home to the quiet beauty of Makena. More than a luxury condominium, D302 is a place to bring generations together, create lasting memories, and experience the very best of Maui. With its extraordinary views, generous living spaces, elegant appointments, and exclusive setting, this is a rare opportunity to own a truly exceptional Makena retreat. Welcome home to Na Hale O Makena D302.

4955 Makena Rd Unit D302, Kihei

Listing courtesy of Coldwell Banker Island Prop(S).

How much is your home worth?

Get instant property value now!