Wailea, HI Homes for Sale with Garage

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  /50

  $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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  /50

  $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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  $1,995,000

  $500K 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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  /33

  $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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  /48

  $2,250,000

  $250K PRICE DROP

  • 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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  /50

  $3,785,000

  $110K PRICE DROP

  • 4 Beds
  • 4 Baths
  • 2,569 Sq Ft

  390 Pualoa Nani Place, Kihei, HI 96753

  Nestled within the prestigious Wailea Pualani community, 390 Pualoa Nani Place offers the essence of luxury island living with privacy, elegance, and the relaxed sophistication that defines Wailea. Surrounded by lush tropical landscaping and swaying palms, this beautifully designed residence welcomes you with a grand driveway entrance and exceptional curb appeal. Inside, the home blends comfort

  Reggie Audant Engel & Volkers Maui

  390 Pualoa Nani Place, Kihei, HI 96753
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  /21

  $3,000,000

  $500K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,416 Sq Ft

  3600 Wailea Alanui Dr Unit 704, Kihei, HI 96753

  Finally, a top-floor unit at Elua Village with a garage. Enjoy the rare combination of a preferred floor plan, ocean view, expansive lanai, and a private garage that is just steps from the sugar white sands of Wailea's Ulua beach and the Elua Village beachfront pool and pavilion. Spacious and inviting, this quiet Wailea condominium home is roomy and relaxing; no upstairs neighbors with this

  Robert McDaniel Wailea Vacation Rentals

  3600 Wailea Alanui Dr Unit 704, Kihei, HI 96753
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  /40

  $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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  /40

  $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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  /30

  $8,895,000

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

  144 Halau Place, Kihei, HI 96753

  Located behind the gates of Wailea Golf Estates, 144 Halau Place is a designer-furnished, single-level contemporary residence offering privacy, ocean and golf course views, and exceptional indoor-outdoor living of over 5,000+ sq. ft. Expansive openings connect the interiors to covered lanais, a striking zero-edge infinity pool and spa, tropical landscaping, and views across the Wailea Blue

  Mark Waite Compass-W

  144 Halau Place, Kihei, HI 96753
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  /48

  $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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  /50

  $11,998,000

  • 4 Beds
  • 5 Baths
  • 5,126 Sq Ft

  14 Halapa Place, Kihei, HI 96753

  Perched atop the exclusive and private enclave of The Ridge at Wailea, this extraordinary Guy Dreier-designed residence is a rare expression of contemporary architecture where architecture, light, and nature exist in perfect harmony. Masterfully built by Trend Builders, this remarkable residence is more than a home—it is a livable sculpture. Every curve, angle, and architectural detail was

  Diane Pool Hawaii Life (W)

  14 Halapa Place, Kihei, HI 96753
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  /45

  $20,500,000

  • 3 Beds
  • 4 Baths
  • 3,279 Sq Ft

  3146 S Kihei Rd, Kihei, HI 96753

  Welcome to the quintessential Maui oceanfront estate, ideally situated on Keawakapu Beach—widely regarded as one of Maui’s most beautiful stretches of sand. This timeless Hawaiian residence embraces its unrivaled setting with approximately 2,500 square feet of covered outdoor living space, perfectly suited for beachfront lounging and entertaining. Designed with architectural integrity and island

  David Richardson Hawaii Life (W)

  3146 S Kihei Rd, Kihei, HI 96753
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  $1,885,000

  $390K 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 wide-plank vinyl flooring, new carpeting, and much more! Owners will love the outstanding garden privacy provided by this peaceful home, while still enjoying peek ocean views from an upstairs bedroom! The Lanai and yard area are a spacious outdoor private sanctuary perfect for entertaining,

  Jeff Simon Hawaii Life (W)

  139 Kai La Place Unit 35B, 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. An advantage of this particular unit location is the North facing lanai to

  Adam Falb Berkshire Hathaway Maui Prop-W

  28 Kai La Place Unit 19A, Kihei, HI 96753
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  $2,399,000

  • 3 Beds
  • 3 Baths
  • 2,129 Sq Ft

  30 Waikai St, Kihei, HI 96753

  Welcome to Wailea Kai, where privacy, luxury, and effortless island living come together in one of Wailea’s most desirable gated communities. This immaculately maintained 3-bedroom, 2.5-bath residence feels both refined and relaxed, with soaring vaulted open-beam ceilings, abundant natural light, dark bamboo flooring, mahogany doors and cabinetry, granite countertops, and plantation shutters

  Sara Romvari Romvari Realty Ltd

  30 Waikai St, Kihei, HI 96753
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  /48

  $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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  /50

  $3,695,000

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

  208 Holomoana Way Unit 14B, Wailea, HI 96753

  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

  Dale Richardson Hawaii Life (W)

  208 Holomoana Way Unit 14B, Wailea, HI 96753
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  /22

  $13,900,000

  • 4 Beds
  • 4 Baths
  • 3,820 Sq Ft

  4000 Wailea Alanui Dr Unit 101, Kihei, HI 96753

  Level One oceanfront at Wailea Point — Hawaii's finest residential condominium, nestled between Wailea Beach and Polo Beach on Maui's coveted Gold Coast. 3,820 SF · 4 bed · 4 bath · 180-degree unobstructed Pacific and island views · 46 feet above the shore. One bedroom functions as a den. From the moment the door opens, the reaction is immediate — an arrival that announces itself before a single

  LaTasha Baldwin Engel & Volkers Maui

  4000 Wailea Alanui Dr Unit 101, Kihei, HI 96753
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  /50

  $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. Owner holds

  Ryan MacLaughlin Island Sotheby's International Realty(W)

  137 Holomoana Way Unit 4A, Kihei, HI 96753
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  /31

  $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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  /50

  $2,495,000

  • 4 Beds
  • 4 Baths
  • 2,490 Sq Ft

  18 Hoohale St, Kihei, HI 96753

  Discover the beauty and privacy of 18 Hoohale Street, a 4-bedroom, 4-bathroom, 2,490 sq. ft. residence with an additional versatile den space. Tucked away on a private cul-de-sac in the highly sought-after Kilohana Ridge neighborhood. Located just across the street from world-famous Keawakapu Beach. This beautifully remodeled home offers privacy, generous living areas, resort-style amenities, and

  Sirena Sastre Montiel Coldwell Banker Island Prop(P)

  18 Hoohale St, Kihei, HI 96753
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  $4,750,000

  $450K 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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  /49

  $2,500,000

  $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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  /50

  $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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  /19

  $490,000

  $9K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 719 Sq Ft

  2747 S Kihei Rd Unit B306, Kihei, HI 96753

  Top-floor corner unit in the highly sought-after “B” building at Kihei Shores—offering added privacy, excellent airflow, and no units above. This 2-bedroom, 2-bath residence features a bright open feel enhanced by fresh interior paint and new flooring in the main living and bedroom areas. The functional layout includes a spacious living area, private lanai, and AC. Originally upgraded in the

  Kokua Realty Kokua Realty LLC

  2747 S Kihei Rd Unit B306, Kihei, HI 96753
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  $11,245,000

  $1M 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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  $3,750,000

  • 3 Beds
  • 3 Baths
  • 3,839 Sq Ft

  3919 Waakaula Place, Kihei, HI 96753

  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

  Geoffrey Cook Century 21 Island Homes

  3919 Waakaula Place, Kihei, HI 96753
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  $3,200,000

  $400K PRICE DROP

  • 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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  $2,350,000

  $45K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 1,894 Sq Ft

  3236 Pikai Way, Kihei, HI 96753

  Welcome to 3236 Pikai Way, an exceptional single-level residence nestled within the exclusive gated enclave of Wailea Kai, just across the street from the golden sands of world-famous Keawakapu Beach. Situated on a quiet private cul-de-sac in Little Wailea Kai, this beautifully maintained 4-bedroom, 3-bath home offers the perfect blend of luxury, privacy, and effortless island living. Designed

  Keoni Fursse Kokua Realty LLC

  3236 Pikai Way, 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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  $639,000

  • 1 Bed
  • 2 Baths
  • 650 Sq Ft

  2575 S Kihei Rd Unit H114, Kihei, HI 96753

  Hotel Zoned. Maui Banyan H114 is a light and bright 1 bedroom, 2 bath ground floor end unit, with easy access and no steps. Kitchen has beautiful bamboo cabinetry, granite countertops, tile backsplash, updated appliances, an island with seating, recessed and under cabinet lighting. Enjoy the comfortable size living room which accommodates a sleeper sofa and recliner chair, flatscreen TV and new

  Jesse Wald Coldwell Banker Island Prop-KP

  2575 S Kihei Rd Unit H114, Kihei, HI 96753
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  /16

  $18,900,000

  $1M PRICE DROP

  • 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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  $36,900,000

  • 5 Beds
  • 6 Baths
  • 6,517 Sq Ft

  34 Maluaka Place Unit 9, Kihei, HI 96753

  This Maui residence spans 6,517 square feet of refined luxury, featuring five spacious bedrooms and five and a half beautifully appointed bathrooms. Designed with seamless indoor-outdoor living, the home showcases breathtaking panoramic ocean views, complemented by sweeping vistas of neighboring islands. Expansive glass walls, elegant finishes, and thoughtfully curated living spaces create an

  Robert Merriman Discovery Makena Realty LLC

  34 Maluaka Place Unit 9, Kihei, HI 96753
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  /19

  $29,900,000

  $9M PRICE DROP

  • 5 Beds
  • 6 Baths
  • 9,176 Sq Ft

  5050 Makena Rd, Kihei, HI 96753

  Perched on one of Makena’s most coveted cliffside locations, this contemporary direct-oceanfront estate is perfectly situated along an intimate cove, offering breathtaking, unobstructed Pacific views from nearly every room. Set on over 22,190 sq. ft. of land, this two-story, five-bedroom, five-and-a-half–bath residence is a masterpiece of luxury and Hawaii’s signature indoor–outdoor living.

  Robert Merriman Discovery Makena Realty LLC

  5050 Makena Rd, Kihei, HI 96753

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