6,955

Wailea, HI Homes

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  • /29

    $630,000

    • 1 Bed
    • 1 Bath
    • 778 Sq Ft

    2737 S Kihei Rd Unit 238, Kihei, HI 96753

    This Beautiful spacious 1BR,1BA nicely updated and fully furnished condo offers an ocean view, luxury vinyl floors, acacia wood countertops in kitchen, split A/C, tasteful furnishings, fully equipped kitchen and in unit laundry. Hale Kamaole is a highly desirable complex directly across the street from Kamaole Beach Park III, one of south Maui's most popular beaches! Kamaole Beach Park III is

    Agent Photo

    Gail Johnson-Wheeler

    Romvari Realty Ltd

    2737 S Kihei Rd Unit 238, Kihei, HI 96753
  • /11

    $4,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,194 Sq Ft
    • Condo for Rent

    3200 Wailea Alanui Dr, Kihei, HI 96753

    BY OWNER/AGENT: PALMS AT WAILEA #608 Beautifully upgraded and furnished B floor plan with laminate wood floors, granite countertops, brand new full size washer/dryer,, new dishwasher, full size refrigerator, new oven/microwave, resort style furnishings, new split AC system, large well furnished lanai, just steps to the very large pool and jacuzzi, BBQ's available to guests, free assigned parking

    Bruce Travis eXp Realty

    3200 Wailea Alanui Dr, Kihei, HI 96753
  • /43

    $1,975,000

    Sold Feb 24, 2026

    59 Wailea Gateway Place Unit 4-103, Kihei, HI 96753

    • 2 Beds
    • 2 Baths
    • 1,248 Sq Ft
    • Built 2018

    Last Sold Summary

    • 1% Below List Price
    • $1,583/SF
    • 3 Days On Market

    Current Estimated Value $1,970,366

    Last Listing Agent Dano Sayles Coldwell Banker Island Prop(S)

    59 Wailea Gateway Place Unit 4-103, Kihei, HI 96753
    • /25

      Not Listed For Sale

      700 Kupulau Dr, Kihei, HI 96753

      700 Kupulau Dr, Kihei, HI 96753

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Rick Brandt Island Sotheby's International Realty(W)

  • /36

    $565,000

    $10K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,035 Sq Ft

    2747 S Kihei Rd Unit E308, Kihei, HI 96753

    Located across the street from one of Maui's best beaches, welcome to Kihei Shores E308, the most affordable 3 bedroom condo on Maui! A clean top-floor, 3-bedroom, 2-bath condo in the desirable South Maui area. This residential condo features a new AC, upgraded bathroom vanities, sleek laminate wood flooring, built-in closet organizers, stripped popcorn ceilings, recent paint work and lighted

    Agent Photo

    Jyoti Graziano

    eXp Realty

    2747 S Kihei Rd Unit E308, Kihei, HI 96753
  • /31

    $7,300 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,796 Sq Ft
    • House for Rent

    83 Kainehe Place, Kihei, HI 96753

    Experience the epitome of resort living in the heart of Wailea with this stunning, fully furnished Kai Malu home. This property boasts three spacious bedrooms and 2.5 well-appointed bathrooms, offering ample space for relaxation and comfort. The home is nestled within a secure, gated community, providing an added layer of peace of mind. The two-car garage offers plenty of room for vehicles or

    83 Kainehe Place, Kihei, HI 96753
  • /35

    $845,000

    Sold Mar 30, 2026

    2777 S Kihei Rd Unit 106, Kihei, HI 96753

    • 1 Bed
    • 2 Baths
    • 849 Sq Ft
    • Built 1990

    Last Sold Summary

    • 15% Below List Price
    • $995/SF
    • 131 Days On Market

    Current Estimated Value $743,798

    Last Listing Agent Clint Hansen Maui Luxury Real Estate LLC

    2777 S Kihei Rd Unit 106, Kihei, HI 96753
    • /28

      Est $506,501

      Not Listed For Sale

      160 Keonekai Rd Unit 8-204, Kihei, HI 96753

      • 2 Beds
      • 2 Baths
      • 750 Sq Ft
      • Built 1992
      160 Keonekai Rd Unit 8-204, Kihei, HI 96753

      Last Sold Summary

      • 77 Days On Market

      Last Listing Agent Rhonda Faleafine Chris Bakeman Realty LLC

  • /25

    $385,000

    • 2 Beds
    • 1 Bath
    • 625 Sq Ft

    160 Keonekai Rd Unit 12-106, Kihei, HI 96753

    Priced Right, Move-In Ready — Your Best Value in Keonekai Villages Finding an affordable 2-bed/1 bath condo with 2 parking spaces (#187 + #188) in Kihei feels nearly impossible right now — but here it is. This is the lowest-priced 2-bedroom in the highly sought-after Keonekai Villages, giving you a real path into the South Maui market without stretching your budget. Tucked on the quiet backside

    Agent Photo

    Theresa Short

    Keller Williams Realty Maui-Ka

    160 Keonekai Rd Unit 12-106, Kihei, HI 96753
  • /49

    $5,000 Per Month

    • 2 Beds
    • 2 Baths
    • 949 Sq Ft
    • Condo for Rent

    3950 Kalai Waa St, Wailea-Makena, HI 96753

    Welcome to Wailea Fairway Villas D-202, as you enter stunning blue Pacific Ocean views. Two bedroom, two bathroom approximately 984 sq. ft. beautifully furnished Villa, with new modern furniture, flat screen TV, remodeled 2023, freshly painted walls, new light fixtures with soffit lighting and dimmer adjustment, new ceiling fans, custom window coverings provide privacy and shade when

    3950 Kalai Waa St, Wailea-Makena, HI 96753
  • /19

    $5,750,000

    Sold Feb 27, 2026

    4000 Wailea Alanui Dr Unit 603, Kihei, HI 96753

    • 2 Beds
    • 2 Baths
    • 1,900 Sq Ft
    • Built 1986

    Last Sold Summary

    • 7% Below List Price
    • $3,026/SF
    • 8 Days On Market

    Current Estimated Value $5,741,618

    Last Listing Agent Nancy J. Callahan Coldwell Banker Island Prop(S)

    4000 Wailea Alanui Dr Unit 603, Kihei, HI 96753
    • /50

      Not Listed For Sale

      2695 S Kihei Rd Unit 5-207, Kihei, HI 96753

      • 1 Bed
      • 2 Baths
      • 653,400 Sq Ft
      • Built 1983
      2695 S Kihei Rd Unit 5-207, Kihei, HI 96753

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Michael Mulski Pacific Image Properties

  • /38

    $2,095,000

    $200K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,088 Sq Ft

    182 Ponana St, Kihei, HI 96753

    Imagine finishing your morning coffee and stepping outside to a 45-foot heated lap pool and spa — in your own backyard. No resort crowds. No reservations. Just warm water and Maui sunshine. 182 Ponana Street sits inside Kihei's highly sought-after Keawakapu Views neighborhood. This 2,088-square-foot single-story home was built in 2018 with one thing in mind: the ultimate Maui lifestyle, no

    Agent Photo

    Eric West

    Real Broker

    182 Ponana St, Kihei, HI 96753
  • /14

    $3,950 Per Month

    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • House for Rent

    825 Kumulani Dr, Kihei, HI 96753

    $3,950 / 2br - 1200ft2 - Maui Meadows 2nd floor 2 bed / 2 bath unit, w/ deck, view, & utilities825 kumulani, Kihei, HI 96753Gorgeous second floor 1200 square foot 2-bedroom, 2-bath unit with a large 340 square foot covered redwood deck, high ceilings, five closets, and an ocean view. The beautiful building is a pole house designed by the renowned Maui architect Frank Stiller.We

    825 Kumulani Dr, Kihei, HI 96753
  • /50

    $1,750,000

    Sold Jun 22, 2026

    30 Ponana St, Kihei, HI 96753

    • 3 Beds
    • 2 Baths
    • 1,912 Sq Ft
    • Built 1999

    Last Sold Summary

    • 11% Below List Price
    • $915/SF
    • 94 Days On Market

    Current Estimated Value $1,881,701

    Last Listing Agent Max Blair Coldwell Banker Island Prop(S)

    30 Ponana St, Kihei, HI 96753
    • /47

      Est $2,647,563

      Not Listed For Sale

      3408 Hookipa Place, Kihei, HI 96753

      • 4 Beds
      • 4 Baths
      • 3,741 Sq Ft
      • Built 2017
      3408 Hookipa Place, Kihei, HI 96753

      Last Sold Summary

      • 89 Days On Market

      Last Listing Agent Eric West Real Broker

  • /50

    $750,000

    • 1 Bed
    • 2 Baths
    • 818 Sq Ft

    2695 S Kihei Rd Unit 9-209, Kihei, HI 96753

    Kamaole Sands 9-209 is a fully furnished vacation rental condominium boasting Pacific Ocean views, tasteful renovations, and a generous-sized covered outdoor deck. This residence is oriented Southwest taking advantage of year-round sunsets, excellent cross-breeze, and protection from the afternoon sun. Close proximity of ocean within the development on the 2nd floor of Building 9. Kamaole Sands

    Agent Photo

    Michael Mulski

    Pacific Image Properties

    2695 S Kihei Rd Unit 9-209, Kihei, HI 96753
  • /51

    $7,750 Per Month

    • 3 Beds
    • 3 Baths
    • 1,574 Sq Ft
    • Townhouse for Rent

    197 Holokahiki Ln, Wailea-Makena, HI 96753

    Welcome home to Makalii! Perched on the hilltop of the Wailea Shore this FULLY FURNISHED 3 bedroom, 3 bathroom condo with a 2 car garage is a rare find.This open floor plan condo, giving you approx. 2,000sqft of indoor and outdoor space. boasts of natural light with floor to ceiling windows and an open floor plan that intensifies the spacious open-air lifestyle desired on Maui. The

    197 Holokahiki Ln, Wailea-Makena, HI 96753
  • /50

    $2,975,000

    Sold Mar 27, 2026

    440 Mikioi Place, Kihei, HI 96753

    • 5 Beds
    • 6 Baths
    • 3,489 Sq Ft
    • Built 1988

    Last Sold Summary

    • 1% Below List Price
    • $853/SF
    • 54 Days On Market

    Current Estimated Value $2,927,015

    Last Listing Agent Sloan Allison Coldwell Banker Island Prop(S)

    440 Mikioi Place, Kihei, HI 96753
    • /50

      Est $505,631

      Not Listed For Sale

      160 Keonekai Rd Unit 17-102, Kihei, HI 96753

      • 2 Beds
      • 2 Baths
      • 756 Sq Ft
      • Built 1992
      160 Keonekai Rd Unit 17-102, Kihei, HI 96753

      Last Sold Summary

      • 132 Days On Market

      Last Listing Agent Aubrey Christopher Keller Williams Realty Maui-Ka

  • /44

    $2,549,000

    $146K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 3,028 Sq Ft

    3291 Waileia Place, Kihei, HI 96753

    Luxury Spanish Villa in Wailea, Maui. Nestled in one of Wailea’s most sought-after neighborhoods, this meticulously upgraded contemporary Spanish villa blends timeless elegance with modern comfort. Situated on over half an acre of prime real estate and boasting over 5,000 square feet of living space under roof, this estate epitomizes luxury island living with single level living, having only the

    Agent Photo

    Alex Iskenderian

    Berkshire Hathaway Maui Prop-L

    3291 Waileia Place, Kihei, HI 96753
  • /29

    $5,950 Per Month

    • 3 Beds
    • 3 Baths
    • 1,568 Sq Ft
    • Condo for Rent

    3950 Kalai Waa St Unit V-101, Wailea-Makena, HI 96753

    Enjoy spectacular panoramic ocean, golf course, and Haleakala views from this Wailea Fairway Villas finely furnished 3-bedroom, 3-bathroom townhome in beautiful Wailea. This spacious end unit features a naturally bright and breezy open floor plan, vaulted ceilings and a well thought out kitchen design, with ample storage and high-end appliances. This 2-story unit is the complete package, with no

    3950 Kalai Waa St Unit V-101, Wailea-Makena, HI 96753
  • 410 Kupulau Dr, Kihei, HI 96753

    $980,000

    Sold Jul 15, 2026

    410 Kupulau Dr, Kihei, HI 96753

    • 3 Beds
    • 2 Baths
    • 1,476 Sq Ft
    • Built 1975

    Last Sold Summary

    • 2% Below List Price
    • $664/SF
    • 55 Days On Market

    Current Estimated Value $1,154,653

    Last Listing Agent Vivian Tran Talk Realty LLC

    410 Kupulau Dr, Kihei, HI 96753
    • /49

      Not Listed For Sale

      2695 S Kihei Rd Unit 10-313, Kihei, HI 96753

      • 1 Bed
      • 2 Baths
      • 818 Sq Ft
      • Built 1983
      2695 S Kihei Rd Unit 10-313, Kihei, HI 96753

      Last Sold Summary

      • 42 Days On Market

      Last Listing Agent Max Blair Coldwell Banker Island Prop(S)

  • /32

    $799,000

    Pending
    • 1 Bed
    • 2 Baths
    • 908 Sq Ft

    155 Wailea Ike Place Unit 68, Kihei, HI 96753

    Welcome to Grand Champions unit 68. This unit has one of Grand Champions' most coveted locations, situated along the fairway on the second hole of the Wailea Blue Golf Course. As you enter the unit you will be delighted by the spacious living room's tall, vaulted ceilings, and the amazing ocean views will please even the most discerning buyer! The large bedroom has an adorable, unique Hawaiian

    Agent Photo

    Marcus Nygren

    Coldwell Banker Island Prop(S)

    155 Wailea Ike Place Unit 68, Kihei, HI 96753
  • /16

    $2,750 Per Month

    • 2 Beds
    • 2 Baths
    • 728 Sq Ft
    • Townhouse for Rent

    2747 S Kihei Rd, Kihei, HI 96753

    Lovely fully furnished two-bedroom, two-bathroom ground-floor unit in Kihei Shores, set in a peaceful garden setting. This well-maintained condo is a joy to view and offers comfortable island living just across the street from the popular Kamaole III Beach Park. Kihei Shores also features a community pool and hot tub, making it an ideal place to relax and enjoy the Maui

    2747 S Kihei Rd, Kihei, HI 96753
  • /28

    $470,000

    Sold Oct 10, 2025

    2747 S Kihei Rd Unit B106, Kihei, HI 96753

    • 2 Beds
    • 2 Baths
    • 719 Sq Ft
    • Built 1992

    Last Sold Summary

    • 5% Below List Price
    • $654/SF
    • 8 Days On Market

    Current Estimated Value $457,449

    Last Listing Agent Marilyn Steinmetz AOK Properties LLC

    2747 S Kihei Rd Unit B106, Kihei, HI 96753
    • /26

      Est $524,615

      Not Listed For Sale

      160 Keonekai Rd Unit 16-104, Kihei, HI 96753

      • 2 Beds
      • 1.5 Baths
      • 673,002 Sq Ft
      • Built 1992
      160 Keonekai Rd Unit 16-104, Kihei, HI 96753

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Kevin Spaise Keller Williams Realty Maui-Ki

  • /37

    $1,449,000

    $326K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,194 Sq Ft

    3200 Wailea Alanui Dr Unit 1505, Kihei, HI 96753

    Experience breathtaking ocean views and unforgettable sunsets from the comfort of your private lanai. This exceptional ground-floor villa is nestled in a highly sought-after inner circle location, where you can unwind with the gentle Hawaiian breezes or take a leisurely stroll to the vibrant community gathering center. The villa boasts a spacious living area with an open dining area and a

    Bob Hansen Maui Luxury Real Estate LLC

    3200 Wailea Alanui Dr Unit 1505, Kihei, HI 96753
  • /40

    $8,300 Per Month

    • 3 Beds
    • 3 Baths
    • 1,802 Sq Ft
    • Townhouse for Rent

    161 Holomoana Way, Wailea-Makena, HI 96753

    Perched in the hilltops of the Wailea sits this FULLY FURNISHED 3 bedroom, 3 bathroom condo with a 1 car garage.This modern condo, has approx. 2500sq ft of indoor and outdoor space, the interior boasts natural light with floor to ceiling windows and an open floor plan that intensifies the spacious open-air lifestyle desired on Maui. The kitchen is designed for entertaining and includes

    161 Holomoana Way, Wailea-Makena, HI 96753
  • /50

    $2,300,000

    Sold Jan 16, 2026

    3600 Wailea Alanui Dr Unit 1101, Kihei, HI 96753

    • 1 Bed
    • 1 Bath
    • 891 Sq Ft
    • Built 1977

    Last Sold Summary

    • 13% Below List Price
    • $2,581/SF
    • 167 Days On Market

    Current Estimated Value $2,351,552

    Last Listing Agent Robbie Dein Maui Real Estate Advisors LLC

    3600 Wailea Alanui Dr Unit 1101, Kihei, HI 96753
    • /27

      Not Listed For Sale

      2695 S Kihei Rd Unit 7-101, Kihei, HI 96753

      • 1 Bed
      • 2 Baths
      • 653,400 Sq Ft
      • Built 1983
      2695 S Kihei Rd Unit 7-101, Kihei, HI 96753

      Last Sold Summary

      • 26 Days On Market

      Last Listing Agent Emalia Fisher Commercial Prop of Maui LLC

  • /42

    $5,750,000

    • 3 Beds
    • 3 Baths
    • 2,521 Sq Ft

    3800 Wailea Alanui Dr Unit 209, Kihei, HI 96753

    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

    Caroline Neubauer Keller Williams Realty Maui-Ka

    3800 Wailea Alanui Dr Unit 209, Kihei, HI 96753
  • /26

    $3,000 Per Month

    • 2 Beds
    • 2 Baths
    • 719 Sq Ft
    • Condo for Rent

    2747 S Kihei Rd Unit H207, Kihei, HI 96753

    Two (2) full bathrooms in this mostly furnished unit.Granite counter tops in kitchenTwo barstool chairs at serving counter.Washer and Dryer in unit for your convenience.Air conditioner.Dining table w/4chairsCeiling fans with lighting.Tile and carpeted floors.Complex supplies pest control spraying quarterly both inside and out.One designated parking space and

    2747 S Kihei Rd Unit H207, Kihei, HI 96753
  • /43

    $1,690,000

    Sold Nov 24, 2025

    2960 S Kihei Rd Unit 209, Kihei, HI 96753

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

    Last Sold Summary

    • 16% Below List Price
    • $2,203/SF
    • 121 Days On Market

    Current Estimated Value $1,675,676

    Last Listing Agent Brett Christiansen Compass-W

    2960 S Kihei Rd Unit 209, Kihei, HI 96753
    • /44

      Not Listed For Sale

      2695 S Kihei Rd Unit 8-104, Kihei, HI 96753

      • 1 Bed
      • 2 Baths
      • 818 Sq Ft
      • Built 1983
      2695 S Kihei Rd Unit 8-104, Kihei, HI 96753

      Last Sold Summary

      • 68 Days On Market

      Last Listing Agent Liza Rivera Keller Williams Realty Maui-Ki

  • /50

    $1,750,000

    $449K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,400 Sq Ft

    53 Waikai St, Kihei, HI 96753

    Motivated Seller — Unbeatable Wailea Value Steps from Keawakapu Beach! The seller is highly motivated, presenting an extraordinary opportunity to secure a beautifully upgraded residence in Wailea Kai, one of South Maui’s most desirable gated communities. This is your chance to capture timeless island luxury with unmatched value in today's market. Designed for effortless comfort, this inviting

    Josef Erlemann Compass-W

    53 Waikai St, Kihei, HI 96753
  • /51

    $6,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,563 Sq Ft
    • Condo for Rent

    172 Holomoana Way Unit 102, Wailea-Makena, HI 96753

    Welcome to Makali‘i, Wailea’s premier private gated resort-style community. Nestled on nearly 9.5 acres, this exclusive enclave features just 68 luxury two- and three-bedroom townhome residences—each building has only four homes for ultimate privacy and tranquility.This finely furnished 2-bedroom, 2-bathroom residence blends mid-century modern design with refined Hawaiian cultural

    172 Holomoana Way Unit 102, Wailea-Makena, HI 96753
  • /50

    $3,870,000

    Sold Jul 20, 2026

    198 Heleuma Place, Kihei, HI 96753

    • 5 Beds
    • 4 Baths
    • 3,934 Sq Ft
    • Built 1990

    Last Sold Summary

    • 8% Below List Price
    • $984/SF
    • 128 Days On Market

    Current Estimated Value $4,111,909

    Last Listing Agent Brandon Janes Sunny Maui Vacations

    198 Heleuma Place, Kihei, HI 96753
    • /13

      Est $559,070

      Not Listed For Sale

      160 Keonekai Rd Unit 11-103, Kihei, HI 96753

      • 2 Beds
      • 1.5 Baths
      • 673,002 Sq Ft
      • Built 1992
      160 Keonekai Rd Unit 11-103, Kihei, HI 96753

      Last Sold Summary

      • 11 Days On Market

      Last Listing Agent Heidi Lynch Hawaii 5-0 Properties, Inc.

Showing Results 41 - 80, Page 2 of 18

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