Wailea, HI Homes for Sale with Garage

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  $1,495,000

  • 5 Beds
  • 4 Baths
  • 1,876 Sq Ft

  2735 Panepoo St, Kihei, HI 96753

  Located in the desirable Keonekai neighborhood of South Kihei, this beautifully maintained multi-unit property has a very flexible floor plan to host a large family and/or create a comfortable rental revenue stream. The upstairs level is a 3-bedroom/2-bath home with soaring vaulted open beam/wood ceilings, fresh paint, abundant natural light, beautiful woodwork, the space feels open, airy, and

  David John Lansing PKR Realty

  2735 Panepoo St, Kihei, HI 96753
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  $5,000,000

  • 4 Beds
  • 4 Baths
  • 3,447 Sq Ft

  557 Kupulau Dr, Kihei, HI 96753

  Welcome to the Resort in Maui Meadows — an extraordinary private estate where jaw-dropping panoramic ocean views, unforgettable sunsets, and elevated island living converge in one of South Maui’s most coveted neighborhoods. Perfectly positioned above the coastline, this exceptional residence captures sweeping vistas stretching across the Pacific Ocean to the neighboring islands, creating a

  Todd Hudson Keller Williams Realty Maui-Ki

  557 Kupulau Dr, Kihei, HI 96753
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  $24,500,000

  $2M PRICE DROP

  • 4 Beds
  • 6 Baths
  • 5,435 Sq Ft

  3060 S Kihei Rd, Kihei, HI 96753

  One-of-a-Kind Keawakapu Beachfront Estate in one of Maui’s most coveted oceanfront settings, offering an extraordinary blend of irreplaceable beach proximity, modern structural integrity, and timeless refined island design. The residence was completely rebuilt from the foundation up, completed in 2013—retaining only the original pool and foundation to preserve its rare, grandfathered beachfront

  Meghan Clair Coldwell Banker Island Prop(S)

  3060 S Kihei Rd, Kihei, HI 96753
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  $2,095,000

  $400K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 1,786 Sq Ft

  19 Kai La Place Unit 43B, Kihei, HI 96753

  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 the ocean and outer islands. Step inside to discover an open-concept kitchen and living room, perfect for both entertaining and everyday living. Wide plank oak flooring graces the upper and lower levels, adding warmth and elegance

  Patrick Franta Coldwell Banker Island Prop(S)

  19 Kai La Place Unit 43B, Kihei, HI 96753
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  $4,495,000

  • 2 Beds
  • 2 Baths
  • 1,558 Sq Ft

  4000 Wailea Alanui Dr Unit 2904, Kihei, HI 96753

  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.

  Kelly Anderson Coldwell Banker Island Prop(P)

  4000 Wailea Alanui Dr Unit 2904, Kihei, HI 96753
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  $4,100,000

  $1M PRICE DROP

  • 3 Beds
  • 4 Baths
  • 2,426 Sq Ft

  12 Hoolei Cir Unit S-2, Kihei, HI 96753

  Arguably south Maui's most exclusive "second home" destination, gated Ho'olei lives like a luxury residential community, with Hotel zoning that offers the option of worry-free short-term rental and immunity from Maui County's proposed vacation rental ban. Private, secure, and impeccably maintained, Ho'olei sets the standard for a secure, luxurious lifestyle and front-and-center access to all that

  Kevin Spaise Keller Williams Realty Maui-Ki

  12 Hoolei Cir Unit S-2, Kihei, HI 96753
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  $2,500,000

  • 3 Beds
  • 2 Baths
  • 2,834 Sq Ft

  3124 Nahenahe Place, Kihei, HI 96753

  Discover one of Maui Meadows' hidden gems at the end of a quiet, private cul-de-sac. This beautifully updated home feels like a modern treehouse, surrounded by stunning ocean, mountain, and sunset views with no wires enjoyed from multiple lanai spaces. The main level features bright, open living, a contemporary kitchen, and a gorgeous primary suite with a soaking tub overlooking the ocean.

  Tom Tezak Hawaii Life (W)

  3124 Nahenahe Place, Kihei, HI 96753
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  $4,999,999

  $100K PRICE DROP

  • 3 Beds
  • 4 Baths
  • 2,426 Sq Ft

  81 Makakehau St Unit H-2, Kihei, HI 96753

  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

  Jan Bryan Coldwell Banker Island Prop(S)

  81 Makakehau St Unit H-2, Kihei, HI 96753
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  /7

  $5,679,000

  • 5 Beds
  • 6 Baths
  • 4,532 Sq Ft

  211 E Ikea Kai Place, Kihei, HI 96753

  Discover the rare opportunity to create your own island sanctuary in the heart of Wailea. Designed to capture sweeping panoramic ocean views, this custom two-story luxury home invites you to personalize every finish and detail to reflect your vision of paradise. With 5 bedrooms and 6 bathrooms across approximately 5,100 square feet of thoughtfully designed living space, the residence is crafted

  Valentin Lopes Coldwell Banker Island Prop-Ku

  211 E Ikea Kai Place, Kihei, HI 96753
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  $2,390,000

  • 3 Beds
  • 2 Baths
  • 1,874 Sq Ft

  108 Ahekolo St, Kihei, HI 96753

  Welcome home to this impeccably maintained, turn-key residence in the highly sought-after Kilohana Ridge community in South Kihei. Thoughtfully designed for comfort and easy island living, the home is filled with natural light as expansive living room windows frame the lush tropical landscaping beyond. Travertine flooring and stainless steel appliances add a refined touch throughout the interior.

  Josh Jerman Hawaii Life (W)

  108 Ahekolo St, Kihei, HI 96753
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  $1,749,900

  Open Sat 10AM - 3PM $50K PRICE DROP

  • 4 Beds
  • 4 Baths
  • 2,700 Sq Ft

  2727 Puu Hoolai St, Kihei, HI 96753

  This well-maintained 2,700 sq. ft. home offers an exceptional, highly flexible layout. The upper level features the main primary bedroom suite and a beautifully remodeled kitchen that opens to a bright living area and a spacious lanai with a hot tub—perfect for indoor-outdoor entertaining. The lower level offers one bedroom with an attached bath, plus two additional separate bedrooms, a newly

  Roger Pleski Coldwell Banker Island Prop(S)

  2727 Puu Hoolai St, Kihei, HI 96753
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  $2,795,000

  $190K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,359 Sq Ft

  4000 Wailea Alanui Dr Unit 3404, Kihei, HI 96753

  You Deserve To Own & Experience Your Oceanfront Paradise Today! Unit 3404 is a delightful 2 bedroom, 2 bathroom upper-level, privately located, & meticulously maintained residence, within the highly-coveted, low density, lushly landscaped, & world-class tropical paradise known as Wailea Point. Upon entering the residence, you are transfixed by the lovely pastoral-framed Ocean, Molokini Crater, &

  Robbie Dein Maui Real Estate Advisors LLC

  4000 Wailea Alanui Dr Unit 3404, Kihei, HI 96753
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  $4,500,000

  • 7 Beds
  • 5 Baths
  • 3,254 Sq Ft

  3264 Keha Dr, Kihei, HI 96753

  E Komo Mai to Your Own Private Paradise Above Wailea. As you pass through the gates, a lush tropical landscape unfolds. Spread across nearly three-quarters of an acre in the heart of Maui Meadows, this private sanctuary welcomes you home. Cascading waterfalls and a tranquil koi pond greet you upon arrival. Perched high above Wailea on the sun-warmed slopes of Haleakala, this estate commands a

  Chelsea Mack eXp Realty

  3264 Keha Dr, Kihei, HI 96753
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  $2,095,000

  $180K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 1,796 Sq Ft

  139 Kai La Place Unit 35B, Kihei, HI 96753

  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! Owners will love the outstanding privacy provided by this wonderful home, while still enjoying ocean views from an upstairs bedroom! Thanks to a very large lawn off the downstairs Lanai no other homes face this Townhouse, making the

  Jeff Simon Hawaii Life (W)

  139 Kai La Place Unit 35B, Kihei, HI 96753
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  $4,975,000

  $400K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,609 Sq Ft

  3600 Wailea Alanui Dr Unit 803, Kihei, HI 96753

  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 and sweeping ocean views from the main living area and Master Suite. Every detail has been refined in this rare 3-bedroom offering (only 7 have come to market in the last 10 years), which is bathed abundantly in natural light

  Kevin Spaise Keller Williams Realty Maui-Ki

  3600 Wailea Alanui Dr Unit 803, Kihei, HI 96753
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  $1,950,000

  $200K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 1,796 Sq Ft

  28 Kai La Place Unit 19A, Kihei, HI 96753

  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 car garage floor and new wi-fi garage door opener as well as new hot water heater with timer, new stainless steel refrigerator, and new lanai sunshades. Also, the new retractable sliding screen door allows the gentle trade winds

  Adam Falb Berkshire Hathaway Maui Prop-W

  28 Kai La Place Unit 19A, Kihei, HI 96753
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  $9,000,000

  • 2 Beds
  • 4 Baths
  • 2,760 Sq Ft

  4584 Makena Rd, Kihei, HI 96753

  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 coastline. Positioned on Poolenalena Beach, the property offers expansive grounds, exceptional privacy, and irreplaceable beach frontage. The existing residence requires renovation, making this an ideal opportunity for investors or end

  Ryan MacLaughlin Island Sotheby's International Realty(W)

  4584 Makena Rd, Kihei, HI 96753
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  $2,875,000

  • 2 Beds
  • 2 Baths
  • 1,374 Sq Ft

  78 Kai Malu Dr Unit 202 (14D), Kihei, HI 96753

  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 beautiful ocean and Molokini views from the spacious lanai. Designed to embrace Maui’s coveted indoor-outdoor lifestyle, this luxury condominium blends modern elegance, comfort, and resort-style amenities within one of South

  Spring Lee Polaris Pacific

  78 Kai Malu Dr Unit 202 (14D), Kihei, HI 96753
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  $2,900,000

  • 3 Beds
  • 3 Baths
  • 1,574 Sq Ft

  137 Holomoana Way Unit 4A, Kihei, HI 96753

  Ocean view residence at Makali'i at Wailea, offered fully furnished with a custom modern interior package. This thoughtfully designed home features contemporary finishes, open-concept living, and seamless indoor-outdoor flow ideal for enjoying Maui’s year-round climate. Located in one of Wailea’s newest communities, just minutes to world-class beaches, golf, dining, and shopping. Currently tenant

  Ryan MacLaughlin Island Sotheby's International Realty(W)

  137 Holomoana Way Unit 4A, Kihei, HI 96753
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  $15,500,000

  • 3 Beds
  • 3 Baths
  • 5,468 Sq Ft

  3002 S Kihei Rd, Kihei, HI 96753

  Hawaiiana meets contemporary design with this exceptional estate on the pristine shores of Keawakapu Beach. The property has been approved for a renovation expanding the home to a 5-bedroom, 5-bath home. Construction to commence early 2026. Beyond the gated entrance lies a world of relaxation and rejuvenation, where quality adjoins an unrivaled location. Upon entering the property, you're

  Josh Jerman Hawaii Life (W)

  3002 S Kihei Rd, Kihei, HI 96753
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  $9,980,000

  • 5 Beds
  • 5 Baths
  • 5,708 Sq Ft

  11 Halapa Place, Kihei, HI 96753

  Nestled within one of Wailea’s most coveted residential settings, this architecturally refined contemporary residence offers an exceptional blend of privacy, design integrity, and resort-style living. Expansive ocean views anchor both the main living level and the elevated primary suite, capturing Maui’s coastline, dramatic skies, and unforgettable sunsets. Walls of Fleetwood sliding glass doors

  Diane Pool Hawaii Life (W)

  11 Halapa Place, Kihei, HI 96753
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  $4,900,000

  $300K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,808 Sq Ft

  4000 Wailea Alanui Dr Unit 2802, Kihei, HI 96753

  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

  Dave Wagner Wailea Point Realty, Inc.

  4000 Wailea Alanui Dr Unit 2802, Kihei, HI 96753
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  $2,500,000

  Open Fri 9:30AM - 6PM $195K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 1,902 Sq Ft

  3142 Waiea Place, Kihei, HI 96753

  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 unique living style with the master on the main level and 2 bedrooms tucked away separately with a jack & jill bath, all 3 with vaulted ceilings. The master has a large lanai that overlooks the pool and lawn area. A major remodel of

  Terence Alling Coldwell Banker Island Prop-Ku

  3142 Waiea Place, Kihei, HI 96753
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  $2,495,000

  • 3 Beds
  • 3 Baths
  • 1,802 Sq Ft

  209 Holokahiki Ln Unit 103, Wailea-Makena, HI 96753

  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 situated in the only building that that faces north, overlooking the Wailea Blue Golf Course with wonderful ocean/sunset views.The orientation of this building provides exceptional privacy and an abundance of natural light from

  Leslie Smith Hawaii Life (W)

  209 Holokahiki Ln Unit 103, Wailea-Makena, HI 96753
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  $14,750,000

  $1M PRICE DROP

  • 4 Beds
  • 5 Baths
  • 4,803 Sq Ft

  19 Malukai Ln Unit 4, Kihei, HI 96753

  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 this community of just 14 bespoke estates, this 4,800+ sq. ft. home is a fusion of contemporary sophistication and the raw, natural beauty of Hawaii. There are four exquisite bedrooms, including a lavish primary suite on the

  Josh Jerman Hawaii Life (W)

  19 Malukai Ln Unit 4, Kihei, HI 96753
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  $9,395,000

  • 3 Beds
  • 4 Baths
  • 3,666 Sq Ft

  144 Halau Place, Kihei, HI 96753

  Set behind the gates of Wailea Golf Estates, this like-new contemporary estate captures the essence of modern Hawaiian luxury. Spanning over 5,000 square feet of indoor-outdoor living, this single level home is designed as a seamless pavilion between architecture and nature, where walls of glass dissolve into tropical gardens and panoramic Pacific vistas. Also available to the qualified buyer is

  Mark Waite Compass-W

  144 Halau Place, Kihei, HI 96753
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  $3,645,000

  $150K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 1,742 Sq Ft

  24 Kai Malu Dr Unit 102 (3B), Kihei, HI 96753

  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 comes with over $400K in luxury furnishings and decor - everything you need to begin the Maui life you’ve earned. Perfectly situated within the community, you will enjoy the pinnacle of island luxury in this exquisite turnkey

  Dale Richardson Hawaii Life (W)

  24 Kai Malu Dr Unit 102 (3B), Kihei, HI 96753
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  $2,750,000

  $25K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 1,574 Sq Ft

  197 Holokahiki Ln Unit 8A, Wailea, HI 96753

  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 the heart of Wailea Resort. This first offering is fully furnished, turnkey, and presented in immaculate condition. Thoughtfully designed with clean architectural lines and subtle mid-century influences, the residence offers 1,574

  Nancy J. Callahan Coldwell Banker Island Prop(S)

  197 Holokahiki Ln Unit 8A, Wailea, HI 96753
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  $11,995,000

  $500K PRICE DROP

  • 3 Beds
  • 4 Baths
  • 2,814 Sq Ft

  3550 Wailea Alanui Dr Unit 801 (F2), Kihei, HI 96753

  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 oceanfront home with full access to the exceptional amenities of the Andaz Hotel including pools, spa, fitness center, beach service, concierge, and award-winning dining. These exclusive residences rarely come to market. This

  Anne Bakoulis Coldwell Banker Island Prop(S)

  3550 Wailea Alanui Dr Unit 801 (F2), Kihei, HI 96753
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  $3,600,000

  • 5 Beds
  • 4 Baths
  • 3,064 Sq Ft

  3435 Hookipa Place Unit A - B - C, Kihei, HI 96753

  NOW AVAILABLE AS A UNIQUE OPPORTUNITY: Three beautifully positioned CPR units with more than 26,300 sq ft of combined land—offering generous space, flexible options, and lasting value for years to come. Experience breathtaking panoramic ocean views from this stunning Unit B of a 3 unit CPR, newly remodeled 2-story home offering 3,064 sq ft of modern coastal living. The open floor plan, with

  Roni Panzarini Equity One Real Estate Inc (M)

  3435 Hookipa Place Unit A - B - C, Kihei, HI 96753
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  $5,900,000

  • 4 Beds
  • 3 Baths
  • 3,059 Sq Ft

  19 Halapa Place, Kihei, HI 96753

  Experience practical elegance in this thoughtfully designed single level custom Wailea home, completed in 2021. Enjoy the magnificent & expansive ocean views, perfect for sunsets & whale watching (during whale season). Perfectly positioned at the top of Wailea in The Ridge at Wailea, a coveted neighborhood with just nine lots. This 4 bedroom, 3 bathroom home with a separate home office blends

  Sherrie Stinger Coldwell Banker Island Prop(S)

  19 Halapa Place, Kihei, HI 96753
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  $2,590,000

  $386K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 1,796 Sq Ft

  339 Kai Malu Place Unit 58B, Kihei, HI 96753

  DREAM LOCATION at KAI MALU with this RARE Developer Unit now Available! Breathtaking views - this is Kai Malu at its best. Beautifully appointed, this pristine home offers that sought after exceptional lifestyle. With the primary bedroom upstairs and balcony perched to behold the most awe-inspiring panorama. Sweeping Wailea Blue Golf Course greens extend upwards to views of towering and majestic

  Katy Foxwell Keller Williams Realty Maui-Ka

  339 Kai Malu Place Unit 58B, Kihei, HI 96753
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  /31

  $749,000

  • 1 Bed
  • 2 Baths
  • 650 Sq Ft

  2575 S Kihei Rd Unit H207, Kihei, HI 96753

  What a fantastic deal. This condo has been upgraded in 2023 with superior upgrades and professional decor. Must see to appreciate. 2 pools, 2 tennis courts, 2 BBQ areas, garage parking. 2 pets under 20#. Low maintenance fees and excellent location in South Kihei. Beach access in minutes, restaurants of all levels within walking and short drive distance. H2 zoning offering security of STR

  Kevin Eliason Maui Paradise Properties LLC

  2575 S Kihei Rd Unit H207, Kihei, HI 96753
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  /16

  $20,000,000

  • 4 Beds
  • 5 Baths
  • 3,834 Sq Ft

  5417 Makena Rd Unit 2, Kihei, HI 96753

  Experience the best of South Maui living in this exclusive Makena Sunset residence, ideally located directly across from Maluaka Beach, Makena, Maui. Enter through a private gated entry to one of only four homes in this intimate and highly sought-after neighborhood. Enjoy the ultimate island lifestyle with the beach just steps away for snorkeling, swimming, and sunsets. This spacious home

  Robert Merriman Discovery Makena Realty LLC

  5417 Makena Rd Unit 2, Kihei, HI 96753
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  $1,325,250

  $70K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 890 Sq Ft

  2575 S Kihei Rd Unit G508, Kihei, HI 96753

  This HOTEL-ZONED, top floor condo in the coveted G Building is a rare find: first time in 10 years a 2BR/2BA unit on the 5th floor of Maui Banyan's premier building is on the market. Panoramic, sweeping views from the ocean to West Maui Mountains to Haleakala. Enjoy sunsets from the lanai and whale sightings during whale season! The Northwest orientation of G508 significantly reduces the solar

  Jeffrey Samuels Jeffrey Samuels Realty

  2575 S Kihei Rd Unit G508, Kihei, HI 96753

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