7,327

Wailea, HI Homes

Section Image
    • /34

      Est $2,019,116

      Not Listed For Sale

      3950 Kalai Waa St Unit E103, Kihei, HI 96753

      • 3 Beds
      • 3 Baths
      • 1,788 Sq Ft
      • Built 1998
      3950 Kalai Waa St Unit E103, Kihei, HI 96753

      Last Sold Summary

      • 85 Days On Market

  • /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
  • /39

    $1,800,000

    Sold Jun 02, 2026

    2960 S Kihei Rd Unit 706, Kihei, HI 96753

    • 2 Beds
    • 2 Baths
    • 767 Sq Ft
    • Built 1973

    Last Sold Summary

    • 9% Below List Price
    • $2,347/SF
    • 98 Days On Market

    Current Estimated Value $1,936,094

    Last Listing Agent Jeff Simon Hawaii Life (W)

    2960 S Kihei Rd Unit 706, Kihei, HI 96753
    • /32

      Est $1,149,520

      Not Listed For Sale

      3950 Kalai Waa St Unit E101, Kihei, HI 96753

      • 2 Beds
      • 2 Baths
      • 949 Sq Ft
      • Built 1998
      3950 Kalai Waa St Unit E101, Kihei, HI 96753

      Last Sold Summary

      • 48 Days On Market

  • /41

    $1,850,000

    • 2 Beds
    • 2 Baths
    • 767 Sq Ft

    2960 S Kihei Rd Unit 615, Kihei, HI 96753

    Mana Kai magic! Peace and privacy are the hallmarks of this fabulous east-end unit with incredible Ocean, Keawakapu Beach, outer island (Molokini and Kahoolawe), and Upcountry views, with Pu’u Ola’i standing proudly to the south and majestic Haleakala to the east. This 2 bedroom, 2 bath gem in this HOTEL ZONED resort is ideally located to be convenient to everything South Kihei and the Wailea

    Jeff Simon Hawaii Life (W)

    2960 S Kihei Rd Unit 615, Kihei, HI 96753
  • /36

    $1,995,000

    Sold Mar 10, 2026

    168 Kainui Loop Unit 63B, Kihei, HI 96753

    • 3 Beds
    • 3 Baths
    • 1,796 Sq Ft
    • Built 2008

    Last Sold Summary

    • 23% Below List Price
    • $1,111/SF
    • 323 Days On Market

    Current Estimated Value $2,445,357

    Last Listing Agent Peter Slate Coldwell Banker Island Prop(S)

    168 Kainui Loop Unit 63B, Kihei, HI 96753
    • /29

      Est $1,151,157

      Not Listed For Sale

      3950 Kalai Waa St Unit D202, Kihei, HI 96753

      • 2 Beds
      • 2 Baths
      • 538,837 Sq Ft
      • Built 1998
      3950 Kalai Waa St Unit D202, Kihei, HI 96753

      Last Sold Summary

      • 20 Days On Market

  • /46

    $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
  • /5

    $1,199,000

    Sold Oct 15, 2025

    769 Kumulani Dr, Wailea-Makena, HI 96753

    • Land
    • 21,780 Sq Ft
    • $2,398,000 per Acre

    Last Sold Summary

    • 14% Below List Price
    • 265 Days On Market

    Last Listing Agent Max Baader Pacific Image Properties

    769 Kumulani Dr, Wailea-Makena, HI 96753
    • /38

      Est $1,867,988

      Not Listed For Sale

      3950 Kalai Waa St Unit D103, Kihei, HI 96753

      • 3 Beds
      • 3 Baths
      • 538,837 Sq Ft
      • Built 1998
      3950 Kalai Waa St Unit D103, Kihei, HI 96753

      Last Sold Summary

      • 50 Days On Market

  • /33

    $799,000

    $101K PRICE DROP Pending
    • 1 Bed
    • 2 Baths
    • 818 Sq Ft

    2695 S Kihei Rd Unit 7-104, Kihei, HI 96753

    Turn-key, ground-floor condo in the highly desirable Kamaole Sands resort, ideally located in the center of the courtyard with easy access to the pool, gym and BBQ areas. Enjoy garden views with a peek of the ocean and sunset skies from the private lanai. This 1 bedroom, 2 bath unit is updated with granite countertops, newer kitchen cabinetry, walk-in showers and tile flooring throughout the

    Justin Shaw Berkshire Hathaway Maui Prop-L

    2695 S Kihei Rd Unit 7-104, Kihei, HI 96753
  • /49

    $2,565,000

    Sold Mar 11, 2026

    3133 Kikihi St Unit Lot 414, Kihei, HI 96753

    • 3 Beds
    • 2 Baths
    • 1,955 Sq Ft
    • Built 1988

    Last Sold Summary

    • 5% Below List Price
    • $1,312/SF
    • 24 Days On Market

    Current Estimated Value $2,512,775

    Last Listing Agent Donna Butterfield Coldwell Banker Island Prop(S)

    3133 Kikihi St Unit Lot 414, Kihei, HI 96753
    • /50

      Est $1,800,769

      Not Listed For Sale

      3950 Kalai Waa St Unit B103, Kihei, HI 96753

      • 3 Beds
      • 3 Baths
      • 1,568 Sq Ft
      • Built 1998
      3950 Kalai Waa St Unit B103, Kihei, HI 96753

      Last Sold Summary

      • 21 Days On Market

  • /48

    $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
  • /50

    $3,300,000

    Sold Jan 07, 2026

    206 Heleuma Place, Kihei, HI 96753

    • 3 Beds
    • 3 Baths
    • 3,169 Sq Ft
    • Built 1994

    Last Sold Summary

    • 6% Below List Price
    • $1,041/SF
    • 33 Days On Market

    Current Estimated Value $3,309,201

    Last Listing Agent Ryan MacLaughlin Island Sotheby's International Realty(W)

    206 Heleuma Place, Kihei, HI 96753
    • /35

      Est $1,061,184

      Not Listed For Sale

      3950 Kalai Waa St Unit A201, Kihei, HI 96753

      • 2 Beds
      • 2 Baths
      • 949 Sq Ft
      • Built 1998
      3950 Kalai Waa St Unit A201, Kihei, HI 96753

      Last Sold Summary

      • 141 Days On Market

  • /50

    $1,590,000

    • 2 Beds
    • 2 Baths
    • 898 Sq Ft

    2994 S Kihei Rd Unit 106, Kihei, HI 96753

    Hale Hui Kai is a true hidden gem on Keawakapu Beach — a boutique oceanfront complex in an unbeatable location. From the moment you step into its quiet, lush walkways, you’re greeted with the timeless charm of old Hawaiiana. This beautifully remodeled ground floor two bedroom, two-bath residence features a thoughtful, creative design throughout. The spacious lanai offers a pleasant view — not

    Mary Kerstulovich Hawaii Life (W)

    2994 S Kihei Rd Unit 106, Kihei, HI 96753
  • /44

    $1,535,000

    Sold Apr 01, 2026

    500A Mikioi Place, Kihei, HI 96753

    • 1 Bed
    • 1 Bath
    • 684 Sq Ft
    • Built 1988

    Last Sold Summary

    • 3% Above List Price
    • $2,244/SF
    • 6 Days On Market

    Last Listing Agent Teresa Nelle Island Sotheby's International Realty(L)

    500A Mikioi Place, Kihei, HI 96753
    • /50

      Est $2,717,115

      Not Listed For Sale

      393 Kai Malu Place Unit 52B, Kihei, HI 96753

      • 3 Beds
      • 4 Baths
      • 1,852 Sq Ft
      • Built 2006
      393 Kai Malu Place Unit 52B, Kihei, HI 96753

      Last Sold Summary

      • 132 Days On Market

  • /19

    $900,000

    Pending
    • 1 Bed
    • 2 Baths
    • 680 Sq Ft

    2936 S Kihei Rd Unit 311, Kihei, HI 96753

    Experience the magic of Maui sunsets from your private lanai at Kihei Surfside, set on 1.5 acres of spectacular oceanfront property. This one-bedroom, one-and-a-half bath condo is located in the hotel zone, allowing short-term rentals while also offering the comfort of a perfect primary or second home. Resort-style amenities include a pool, barbecue area, putting green, and an expansive park-like

    Debra Merle Island Sotheby's International Realty(M)

    2936 S Kihei Rd Unit 311, Kihei, HI 96753
  • /47

    $1,125,000

    Sold Apr 27, 2026

    3150 Wailea Alanui Dr Unit 2504, Kihei, HI 96753

    • 2 Beds
    • 2 Baths
    • 1,194 Sq Ft
    • Built 1992

    Last Sold Summary

    • 34% Below List Price
    • $942/SF
    • 353 Days On Market

    Current Estimated Value $1,414,754

    Last Listing Agent Amy Ellul Coldwell Banker Island Prop(S)

    3150 Wailea Alanui Dr Unit 2504, Kihei, HI 96753
    • /50

      Est $2,789,454

      Not Listed For Sale

      148 Kai La Place Unit 31A, Kihei, HI 96753

      • 3 Beds
      • 3 Baths
      • 1,852 Sq Ft
      • Built 2006
      148 Kai La Place Unit 31A, Kihei, HI 96753

      Last Sold Summary

      • 3 Days On Market

  • /33

    $999,000

    $137K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,052 Sq Ft

    2777 S Kihei Rd Unit C208, Kihei, HI 96753

    Welcome to Maui Kamaole, one of South Maui's most sought-after resort communities. Set on 23 acres of beautifully maintained tropical grounds, this low-rise complex offers a rare sense of privacy, space, and serenity in an unbeatable Kihei location-just moments from Wailea and some of the best beaches on Maui. This 2-bedroom, 2-bath townhouse-style condominium is perched above the front pool,

    Jan Bryan Coldwell Banker Island Prop(S)

    2777 S Kihei Rd Unit C208, Kihei, HI 96753
  • /49

    $1,900,000

    Sold Mar 23, 2026

    3150 Wailea Alanui Dr Unit 2902, Kihei, HI 96753

    • 2 Beds
    • 3 Baths
    • 1,559 Sq Ft
    • Built 1992

    Last Sold Summary

    • 17% Below List Price
    • $1,219/SF
    • 115 Days On Market

    Current Estimated Value $1,928,912

    Last Listing Agent Bradley MacArthur Hawaii Life (W)

    3150 Wailea Alanui Dr Unit 2902, Kihei, HI 96753
    • /40

      Est $1,202,197

      Not Listed For Sale

      155 Wailea Ike Place Unit 172, Kihei, HI 96753

      • 1 Bed
      • 2 Baths
      • 908 Sq Ft
      • Built 1990
      155 Wailea Ike Place Unit 172, Kihei, HI 96753

      Last Sold Summary

      • 75 Days On Market

  • /50

    $3,895,000

    • 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
  • /34

    $4,150,000

    Sold Jun 03, 2026

    4850 Makena Alanui Unit F207, Kihei, HI 96753

    • 2 Beds
    • 2 Baths
    • 1,313 Sq Ft
    • Built 1984

    Last Sold Summary

    • 8% Below List Price
    • $3,161/SF
    • 98 Days On Market

    Current Estimated Value $4,405,106

    Last Listing Agent David McAlear Coldwell Banker Island Prop-Ku

    4850 Makena Alanui Unit F207, Kihei, HI 96753
    • /32

      Est $1,482,330

      Not Listed For Sale

      155 Wailea Ike Place Unit 106, Kihei, HI 96753

      • 3 Beds
      • 2 Baths
      • 1,383 Sq Ft
      • Built 1989
      155 Wailea Ike Place Unit 106, Kihei, HI 96753

      Last Sold Summary

      • 9 Days On Market

  • /21

    $3,250,000

    $250K 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
  • /50

    $1,525,000

    Sold Jul 28, 2025

    2709 Puu Hoolai St, Kihei, HI 96753

    • 3 Beds
    • 3 Baths
    • 2,180 Sq Ft
    • Built 1989

    Last Sold Summary

    • 6% Below List Price
    • $700/SF
    • 86 Days On Market

    Current Estimated Value $1,508,947

    Last Listing Agent Kimberly Sloan REMAX Hawaii Maui

    2709 Puu Hoolai St, Kihei, HI 96753
    • /33

      Est $1,300,723

      Not Listed For Sale

      155 Wailea Ike Place Unit 99, Kihei, HI 96753

      • 2 Beds
      • 2 Baths
      • 1,056 Sq Ft
      • Built 1990
      155 Wailea Ike Place Unit 99, Kihei, HI 96753

      Last Sold Summary

      • 153 Days On Market

  • /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
  • /50

    $2,375,000

    Sold Jan 29, 2026

    124 Waaula Place, Kihei, HI 96753

    • 3 Beds
    • 4 Baths
    • 2,526 Sq Ft
    • Built 1985

    Last Sold Summary

    • 11% Below List Price
    • $940/SF
    • 71 Days On Market

    Current Estimated Value $2,389,606

    Last Listing Agent Bradley MacArthur Hawaii Life (W)

    124 Waaula Place, Kihei, HI 96753
    • /43

      Est $1,259,384

      Not Listed For Sale

      155 Wailea Ike Place Unit 92, Kihei, HI 96753

      • 1 Bed
      • 2 Baths
      • 908 Sq Ft
      • Built 1990
      155 Wailea Ike Place Unit 92, Kihei, HI 96753

      Last Sold Summary

      • 37 Days On Market

  • /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
  • /27

    $769,000

    Sold Jun 26, 2026

    2695 S Kihei Rd Unit 2-301, Kihei, HI 96753

    • 2 Beds
    • 2 Baths
    • 1,036 Sq Ft
    • Built 1983

    Last Sold Summary

    • 22% Below List Price
    • $742/SF
    • 353 Days On Market

    Last Listing Agent Michelle Collatos-Ruml Keller Williams Realty Maui-Ka

    2695 S Kihei Rd Unit 2-301, Kihei, HI 96753
    • /29

      Est $1,710,797

      Not Listed For Sale

      155 Wailea Ike Place Unit 83, Kihei, HI 96753

      • 3 Beds
      • 2 Baths
      • 1,383 Sq Ft
      • Built 1990
      155 Wailea Ike Place Unit 83, Kihei, HI 96753

      Last Sold Summary

      • 47 Days On Market

  • /29

    $520,000

    • 2 Beds
    • 2 Baths
    • 756 Sq Ft

    160 Keonekai Rd Unit 27-201, Kihei, HI 96753

    Welcome to Keonekai Villages, a residential condominium in South Kihei, ideally located just up the road from Kamaole III Beach Park and minutes from Wailea. This desirable top-floor unit offers 2 bedrooms and 2 baths, featuring the largest floor plan available in the complex. Tucked in the corner of building 27, this condo is set back from the road, offering added privacy. Pet owners will

    Gabriela Ramirez eXp Realty

    160 Keonekai Rd Unit 27-201, Kihei, HI 96753
  • /48

    $4,550,000

    Sold Apr 14, 2026

    4000 Wailea Alanui Dr Unit 3003, Kihei, HI 96753

    • 2 Beds
    • 3 Baths
    • 1,620 Sq Ft
    • Built 1987

    Last Sold Summary

    • 16% Below List Price
    • $2,809/SF
    • 209 Days On Market

    Current Estimated Value $4,477,535

    Last Listing Agent Dave Wagner Wailea Point Realty, Inc.

    4000 Wailea Alanui Dr Unit 3003, Kihei, HI 96753
    • /27

      Est $1,292,795

      Not Listed For Sale

      155 Wailea Ike Place Unit 51, Kihei, HI 96753

      • 2 Beds
      • 2 Baths
      • 1,056 Sq Ft
      • Built 1990
      155 Wailea Ike Place Unit 51, Kihei, HI 96753

      Last Sold Summary

      • 81 Days On Market

Showing Results 521 - 560, Page 14 of 18

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