Wailea, HI Homes

• 

  

  

  /50

  Est $1,646,970

  Not Listed For Sale

  2757 Kauhale St, Kihei, HI 96753

  • 5 Beds
  • 3 Baths
  • 2,241 Sq Ft
  • Built 1985

  2757 Kauhale St, Kihei, HI 96753

  Last Sold Summary

  • 2 Days On Market
• 

  

  

  /50

  $2,395,000

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

  66 Kai La Place Unit 22A, Kihei, HI 96753

  Welcome to one of Maui's best kept secrets. This exceptional Kai Malu residence offers gorgeous ocean views from the primary suite and both lanais. The home is offered fully furnished, thoughtfully equipped with everything you’d need to settle in comfortably from day one. Recent upgrades include fresh interior paint, new blinds, a new A/C system in 2025, and whole home water filtration insuring a

  Christopher Bannowsky eXp Realty

  66 Kai La Place Unit 22A, Kihei, HI 96753
• 

  

  

  /39

  $1,435,000

  Sold Dec 31, 2025

  10 Wailea Ekolu Place Unit 405, Kihei, HI 96753

  • 2 Beds
  • 2 Baths
  • 1,071 Sq Ft
  • Built 1979

  Last Sold Summary

  • 18% Below List Price
  • $1,340/SF
  • 242 Days On Market

  Current Estimated Value $1,445,007

  Last Listing Agent Robbie Dein Maui Real Estate Advisors LLC

  10 Wailea Ekolu Place Unit 405, Kihei, HI 96753
• 

  

  

  /25

  Est $1,332,770

  Not Listed For Sale

  2751 Kauhale St, Kihei, HI 96753

  • 3 Beds
  • 2 Baths
  • 1,536 Sq Ft
  • Built 1987

  2751 Kauhale St, Kihei, HI 96753

  Last Sold Summary

  • 45 Days On Market
• 

  

  

  /50

  $4,995,000

  Open Mon 11AM - 5PM

  • 2 Beds
  • 2 Baths
  • 1,644 Sq Ft

  4850 Makena Alanui Unit A101, Kihei, HI 96753

  This truly one of a kind masterpiece villa in highly coveted Makena Surf Resort is an exceptional example of quintessential beachfront living at its finest. With a complete studs-out renovation completed in 2022, the meticulous nature and curated bespoke design of this stunning villa is highly evident the moment you enter. The contemporary modern finishes of this sensational ground level

  Max Blair Coldwell Banker Island Prop(S)

  4850 Makena Alanui Unit A101, Kihei, HI 96753
• 

  

  /50

  $3,850,000

  Sold Apr 27, 2026

  3387 Kuaua Place, Kihei, HI 96753

  • 3 Beds
  • 3 Baths
  • 3,146 Sq Ft
  • Built 2002

  Last Sold Summary

  • 4% Below List Price
  • $1,224/SF
  • 43 Days On Market

  Current Estimated Value $3,808,112

  Last Listing Agent Tom Tezak Hawaii Life (W)

  3387 Kuaua Place, Kihei, HI 96753
• 

  

  /45

  Est $1,624,119

  Not Listed For Sale

  2715 Kauhale St, Kihei, HI 96753

  • 4 Beds
  • 4 Baths
  • 2,509 Sq Ft
  • Built 1987

  2715 Kauhale St, Kihei, HI 96753

  Last Sold Summary

  • 135 Days On Market
• 

  

  /48

  $4,795,000

  Pending

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

  63 Hoolei Cir Unit B5, Kihei, HI 96753

  First time offered for sale since the original developer offering. Villa 63-5 is without a doubt one of the best locations in Ho'olei. Positioned on the coveted top row with sweeping ocean views and exceptional privacy. This villa enjoys an elevated setting that enhances view corridors, natural light, and cooling trade winds, creating a true indoor-outdoor Wailea lifestyle, with views of

  Dano Sayles Coldwell Banker Island Prop(S)

  63 Hoolei Cir Unit B5, Kihei, HI 96753
• 

  

  /43

  $975,000

  Sold Jul 09, 2025

  2737 S Kihei Rd Unit 221, Kihei, HI 96753

  • 2 Beds
  • 2 Baths
  • 1,112 Sq Ft
  • Built 1974

  Last Sold Summary

  • 2% Below List Price
  • $877/SF
  • 3 Days On Market

  Current Estimated Value $905,197

  Last Listing Agent Robyn Curletti Compass

  2737 S Kihei Rd Unit 221, Kihei, HI 96753
• 

  

  /50

  Est $1,490,484

  Not Listed For Sale

  235 Hoohale Place, Kihei, HI 96753

  • 4 Beds
  • 3 Baths
  • 1,932 Sq Ft
  • Built 1986

  235 Hoohale Place, Kihei, HI 96753

  Last Sold Summary

  • 229 Days On Market
• 

  

  /50

  $3,295,000

  Open Mon 10AM - 12PM $300K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,347 Sq Ft

  3600 Wailea Alanui Dr Unit 2201, Kihei, HI 96753

  Aloha from Wailea Elua; WE ARE OPEN THIS MONTH FOR EASY VIEWINGS!!! Wailea Elua is one of Wailea's premier properties with direct beach/ocean access that is HOTEL/RESORT ZONED :)!! This allows owners the ability to "Short Term Vacation Rental" to generate income!! This is an added premium valuation in todays market - as all and any Maui properties from here on will be zoned for long term rental

  Bruce McDonald Coldwell Banker Island Prop(S)

  3600 Wailea Alanui Dr Unit 2201, Kihei, HI 96753
• 

  

  /50

  $2,725,000

  Sold May 19, 2026

  4000 Wailea Alanui Dr Unit 3304, Kihei, HI 96753

  • 2 Beds
  • 2 Baths
  • 1,359 Sq Ft
  • Built 1987

  Last Sold Summary

  • 8% Below List Price
  • $2,005/SF
  • 74 Days On Market

  Current Estimated Value $2,891,628

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

  4000 Wailea Alanui Dr Unit 3304, Kihei, HI 96753
• 

  

  /30

  Est $2,023,652

  Not Listed For Sale

  2852 Puu Hoolai St, Kihei, HI 96753

  • 5 Beds
  • 5 Baths
  • 3,408 Sq Ft
  • Built 1989

  2852 Puu Hoolai St, Kihei, HI 96753

  Last Sold Summary

  • 23 Days On Market
• 

  

  /50

  $3,999,000

  $1M PRICE DROP

  • 3 Beds
  • 4 Baths
  • 3,076 Sq Ft

  24 Hoolei Cir Unit T-1, Kihei, HI 96753

  OUTSTANDING NEW PRICE, LARGEST FLOOR PLAN - LOWEST PRICED AND ONLY END UNIT ON THE MARKET AT HO'OLEI TODAY - this Luxury resort villa situated conveniently at the doorstep to Grand Wailea, Wailea Beach, for an elevated lifestyle landing in the hub of paradise. Split level townhome unit T-1, offers great privacy coupled with being the largest floor plan, (Hibiscus), in a most desired end unit

  Katy Foxwell Keller Williams Realty Maui-Ka

  24 Hoolei Cir Unit T-1, Kihei, HI 96753
• 

  

  /42

  $1,200,000

  Sold May 04, 2026

  219 Hoohale Place, Kihei, HI 96753

  • 3 Beds
  • 2 Baths
  • 1,241 Sq Ft
  • Built 1977

  Last Sold Summary

  • 8% Below List Price
  • $967/SF
  • 12 Days On Market

  Current Estimated Value $1,237,978

  Last Listing Agent Terence Alling Coldwell Banker Island Prop-Ku

  219 Hoohale Place, Kihei, HI 96753
• 

  

  /49

  Est $1,360,370

  Not Listed For Sale

  2825 Kauhale St, Kihei, HI 96753

  • 2 Beds
  • 2 Baths
  • 1,225 Sq Ft
  • Built 1985

  2825 Kauhale St, Kihei, HI 96753

  Last Sold Summary

  • 93 Days On Market
• 

  

  /40

  $4,495,770

  $503K PRICE DROP

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

  99 Hoolei Cir Unit E5, Kihei, HI 96753

  Special properties like Ho’olei Villa 99-5 rarely become available. A premier top-row, turn-key townhome with one of the best locations in the entire community! When you get up to the 4th tier of the Ho'olei neighborhood, you can see clearly over the Grand Wailea Resort and the Four Seasons Wailea. With the 180-degree view, gorgeous sunsets are enjoyed year-round. Each of the 3 bedrooms in this

  Dano Sayles Coldwell Banker Island Prop(S)

  99 Hoolei Cir Unit E5, Kihei, HI 96753
• 

  

  /9

  $750,000

  Sold May 28, 2026

  3546 Akala Dr, Wailea-Makena, HI 96753

  • Land
  • 22,563 Sq Ft
  • $1,447,882 per Acre

  Last Sold Summary

  • 35% Below List Price
  • 142 Days On Market

  Current Estimated Value $969,229

  Last Listing Agent Scott Nashiwa Pono Real Estate LLC

  3546 Akala Dr, Wailea-Makena, HI 96753
• 

  

  /49

  Est $1,524,978

  Not Listed For Sale

  2817 Panepoo St, Kihei, HI 96753

  • 3 Beds
  • 3 Baths
  • 2,208 Sq Ft
  • Built 1988

  2817 Panepoo St, Kihei, HI 96753

  Last Sold Summary

  • 4 Days On Market
• 

  

  /48

  $7,495,000

  Pending

  • 3 Beds
  • 3 Baths
  • 2,163 Sq Ft

  4000 Wailea Alanui Dr Unit 1103, Kihei, HI 96753

  Perfectly positioned on a rare elevated promontory directly above the revered Wailea beach walk, this front-row residence boasts commanding, unobstructed ocean, outer island, and verdant coastline views from throughout the main living area. You are as close to the ocean as Wailea allows. The arrival sets the tone. A light-filled atrium, lush with tropical specimens, leads to the book-matched

  Robbie Dein Maui Real Estate Advisors LLC

  4000 Wailea Alanui Dr Unit 1103, Kihei, HI 96753
• 

  

  /22

  $1,475,000

  Sold Mar 19, 2026

  3300 Wailea Alanui Dr Unit 13F, Kihei, HI 96753

  • 1 Bed
  • 2 Baths
  • 966 Sq Ft
  • Built 1976

  Last Sold Summary

  • $1,527/SF
  • 0 Days On Market

  Current Estimated Value $1,667,883

  Last Listing Agent Raphael Wellerstein Coldwell Banker Island Prop-Ku

  3300 Wailea Alanui Dr Unit 13F, Kihei, HI 96753
• 

  

  /18

  Est $1,542,921

  Not Listed For Sale

  2844 Panepoo St, Kihei, HI 96753

  • 5 Beds
  • 5 Baths
  • 2,828 Sq Ft
  • Built 1985

  2844 Panepoo St, Kihei, HI 96753

  Last Sold Summary

  • 308 Days On Market
• 

  

  /19

  $2,495,000

  $55K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 3,195 Sq Ft

  199 E Ikea Moku Place, Kihei, HI 96753

  INCREDIBLE OPPORTUNITY for the right Buyer! Welcome to 199 E. Ikea Moku Place, a refined Wailea residence offering the PERFECT BLEND OF PRIVACY, COMFORT AND WORLD CLASS SURROUNDINGS. Located on a quiet cul-de-sac in the prestigious gated enclave of Wailea Kialoa, this 3,195 sq. ft. home is perfectly positioned to capture SPECTACULAR SWEEPING OCEAN AND OUTER ISLAND VIEWS. Here, life unfolds to the

  Robbie Dein Maui Real Estate Advisors LLC

  199 E Ikea Moku Place, Kihei, HI 96753
• 

  

  /50

  $4,000,000

  Sold Nov 07, 2025

  4281 Wailina Place, Kihei, HI 96753

  • 3 Beds
  • 4 Baths
  • 3,817 Sq Ft
  • Built 2002

  Last Sold Summary

  • 13% Below List Price
  • $1,048/SF
  • 66 Days On Market

  Current Estimated Value $4,063,075

  Last Listing Agent Kathy Worley Pali Kai Inc

  4281 Wailina Place, Kihei, HI 96753
• 

  

  /50

  Est $1,277,919

  Not Listed For Sale

  2866 Ohina St, Kihei, HI 96753

  • 4 Beds
  • 3 Baths
  • 1,593 Sq Ft
  • Built 1983

  2866 Ohina St, Kihei, HI 96753

  Last Sold Summary

  • 12 Days On Market
• 

  

  /48

  $3,495,000

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

  244 Holomoana Way Unit 17B, Wailea, HI 96753

  Makalii at Wailea 17B is a standout villa commanding the premier ocean-view position in the entire development, offering unobstructed, sweeping vistas of the Pacific, Molokini, and Kahoolawe. Elevated and ideally oriented, this residence captures Maui’s most iconic sunsets and seasonal whale activity from the comfort of home. Equally impressive is the interior, where impeccably curated,

  Max Blair Coldwell Banker Island Prop(S)

  244 Holomoana Way Unit 17B, Wailea, HI 96753
• 

  

  /50

  $1,895,000

  Sold Jan 30, 2026

  95 Poailani Place Unit 19, Kihei, HI 96753

  • 3 Beds
  • 3 Baths
  • 2,229 Sq Ft
  • Built 2006

  Last Sold Summary

  • $850/SF
  • 78 Days On Market

  Current Estimated Value $1,873,684

  Last Listing Agent Carol Olsen Coldwell Banker Island Prop(S)

  95 Poailani Place Unit 19, Kihei, HI 96753
• 

  

  /43

  Est $1,483,535

  Not Listed For Sale

  289 Aukahi St, Kihei, HI 96753

  • 3 Beds
  • 2 Baths
  • 1,712 Sq Ft
  • Built 1985

  289 Aukahi St, Kihei, HI 96753

  Last Sold Summary

  • 45 Days On Market
• 

  

  /46

  $1,288,880

  $49K PRICE DROP

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

  3200 Wailea Alanui Dr Unit 2105, Kihei, HI 96753

  Welcome to Palms at Wailea 2105, a freshly re-imagined 2024 renovation that offers a modern, fully furnished 2-bedroom, 2-bath retreat in one of South Maui's most sought-after communities. This turn-key condo captures the essence of island living while delivering the proven performance of a top-producing vacation rental, making it an ideal choice for investors or owners ready to enjoy the island

  Mark Morris Coldwell Banker Island Prop(P)

  3200 Wailea Alanui Dr Unit 2105, Kihei, HI 96753
• 

  

  /47

  $1,499,750

  Sold Jul 29, 2025

  2927 Kauhale St, Kihei, HI 96753

  • 3 Beds
  • 3 Baths
  • 1,832 Sq Ft
  • Built 1985

  Last Sold Summary

  • 8% Below List Price
  • $819/SF
  • 95 Days On Market

  Current Estimated Value $1,487,543

  Last Listing Agent Sherrie Stinger Coldwell Banker Island Prop(S)

  2927 Kauhale St, Kihei, HI 96753
• 

  

  /45

  Est $1,564,699

  Not Listed For Sale

  2688 Ohina St, Kihei, HI 96753

  • 3 Beds
  • 2 Baths
  • 1,684 Sq Ft
  • Built 1979

  2688 Ohina St, Kihei, HI 96753

  Last Sold Summary

  • 126 Days On Market
• 

  

  /47

  $639,000

  • 1 Bed
  • 2 Baths
  • 817 Sq Ft

  2881 S Kihei Rd Unit 107, Kihei, HI 96753

  Tucked into the lush tropical grounds of Maui Hill, Unit 107—lovingly known as the “Honeymoon Suite”—captures the warmth, romance, and easy rhythm of South Maui living. This spacious 1-bedroom, 2-bath residence offers over 800 square feet of island comfort, filled with natural light, gentle trade winds, and beautiful ocean views that invite you to slow down and savor each moment. Thoughtfully

  Alana Rucynski Hawaii Life (W)

  2881 S Kihei Rd Unit 107, Kihei, HI 96753
• 

  

  /50

  $1,750,000

  Sold Dec 30, 2025

  147 Hoohale St, Kihei, HI 96753

  • 4 Beds
  • 3 Baths
  • 2,447 Sq Ft
  • Built 2003

  Last Sold Summary

  • 8% Below List Price
  • $715/SF
  • 18 Days On Market

  Current Estimated Value $1,832,043

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

  147 Hoohale St, Kihei, HI 96753
• 

  

  /15

  Est $1,248,626

  Not Listed For Sale

  2780 Ohina St, Kihei, HI 96753

  • 2 Beds
  • 2 Baths
  • 1,216 Sq Ft
  • Built 1988

  2780 Ohina St, Kihei, HI 96753

  Last Sold Summary

  • 5 Days On Market
• 

  

  /24

  $879,000

  • Land
  • 7,892 Sq Ft
  • $4,851,047 per Acre

  124 Hokai Place Unit 20, Kihei, HI 96753

  Now is your opportunity to build your custom dream home in one of South Kihei’s most desirable neighborhoods—Kilohana Hema. This exceptional homesite is ideally situated adjacent to Wailea and just a short stroll from the golden sands of Keawakapu Beach. Spanning approximately 7,893 square feet, this prime lot is part of an exclusive enclave of just 23 single-family homes, offering both privacy

  Kristen Kingwell Coldwell Banker Island Prop-KP

  124 Hokai Place Unit 20, Kihei, HI 96753
• 

  

  /29

  $2,200,000

  Sold Jan 16, 2026

  3379 Kehala Dr, Kihei, HI 96753

  • 2 Beds
  • 3 Baths
  • 2,316 Sq Ft
  • Built 1977

  Last Sold Summary

  • 4% Below List Price
  • $950/SF
  • 27 Days On Market

  Current Estimated Value $2,184,738

  Last Listing Agent John Lyle Coldwell Banker Island Prop(S)

  3379 Kehala Dr, Kihei, HI 96753
• 

  

  /46

  Est $1,933,891

  Not Listed For Sale

  277 Keonekai Rd, Kihei, HI 96753

  • 3 Beds
  • 2 Baths
  • 3,072 Sq Ft
  • Built 1970

  277 Keonekai Rd, Kihei, HI 96753

  Last Sold Summary

  • 40 Days On Market
• 

  

  /39

  $1,149,000

  $150K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,052 Sq Ft

  2777 S Kihei Rd Unit 219, Kihei, HI 96753

  Priced to Sell! This 2bd/2bth unit in Maui Kamaole boasts impressive ocean and West Maui mountain views, and is perfectly situated in the complex between the two gorgeous pool areas. The spacious floor plan offers plenty of living space as well as 3 separate lanais, and being a corner unit provides an extra living room window for added natural light. Both bathrooms have been remodeled with

  Jordan Kamikawa Hawaii Life (W)

  2777 S Kihei Rd Unit 219, Kihei, HI 96753
• 

  

  /47

  $525,000

  Sold Aug 29, 2025

  160 Keonekai Rd Unit 11-201, Kihei, HI 96753

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

  Last Sold Summary

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

  Current Estimated Value $514,247

  Last Listing Agent Melissa Montgomery Coldwell Banker Island Prop(S)

  160 Keonekai Rd Unit 11-201, Kihei, HI 96753
• 

  

  /37

  Est $1,097,053

  Not Listed For Sale

  2777 S Kihei Rd Unit C201, Kihei, HI 96753

  • 2 Beds
  • 2 Baths
  • 1,015,819 Sq Ft
  • Built 1989

  2777 S Kihei Rd Unit C201, Kihei, HI 96753

  Last Sold Summary

  • 42 Days On Market

Showing Results 161 - 200, Page 5 of 18