Wailea, HI Homes

• 

  

  

  /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
• 

  

  

  /50

  $1,820,000

  Sold Aug 04, 2025

  2733 Puu Hoolai St, Kihei, HI 96753

  • 5 Beds
  • 4 Baths
  • 2,788 Sq Ft
  • Built 1989

  Last Sold Summary

  • 19% Below List Price
  • $653/SF
  • 192 Days On Market

  Current Estimated Value $1,788,628

  Last Listing Agent Todd Hudson Keller Williams Realty Maui-Ki

  2733 Puu Hoolai St, Kihei, HI 96753
• 

  

  

  /48

  Est $1,547,048

  Not Listed For Sale

  155 Wailea Ike Place Unit 48, Kihei, HI 96753

  • 2 Beds
  • 2 Baths
  • 1,148 Sq Ft
  • Built 1989

  155 Wailea Ike Place Unit 48, Kihei, HI 96753

  Last Sold Summary

  • 360 Days On Market
• 

  

  

  /32

  $1,275,000

  $74K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,242 Sq Ft

  3200 Wailea Alanui Dr Unit 1605, Kihei, HI 96753

  Discover Unbeatable Wailea Value Experience the perfect blend of affordability and luxury in the prestigious Palms at Wailea. This inviting, turnkey furnished, ground-level, 2-bedroom, 2-bath residence in Building 16 is priced as one of the most accessible two-bedrooms in the complex, presenting a rare opportunity to own in this sought-after community. The unit is designed for comfort and privacy

  Kathleen Tezak Island Sotheby's International Realty(W)

  3200 Wailea Alanui Dr Unit 1605, Kihei, HI 96753
• 

  

  

  /28

  $533,000

  Sold Mar 06, 2026

  3300 Wailea Alanui Dr Unit 39D, Kihei, HI 96753

  • 1 Bed
  • 1 Bath
  • 792 Sq Ft
  • Built 1976

  Last Sold Summary

  • 33% Above List Price
  • $673/SF
  • 15 Days On Market

  Current Estimated Value $1,205,000

  Last Listing Agent Don McEntire McEntire Realty

  3300 Wailea Alanui Dr Unit 39D, Kihei, HI 96753
• 

  

  /50

  Est $1,506,832

  Not Listed For Sale

  155 Wailea Ike Place Unit 42, Kihei, HI 96753

  • 2 Beds
  • 2 Baths
  • 1,148 Sq Ft
  • Built 1990

  155 Wailea Ike Place Unit 42, Kihei, HI 96753

  Last Sold Summary

  • 92 Days On Market
• 

  

  /31

  $2,950,000

  • 1 Bed
  • 2 Baths
  • 1,031 Sq Ft

  3600 Wailea Alanui Dr Unit 2012, Kihei, HI 96753

  Welcome to Wailea Elua, an exclusive oceanfront, hotel-zoned vacation rental set atop a lush greenbelt in prestigious Wailea. Spanning 24 acres of tropical paradise, this sought-after community offers an unparalleled blend of luxury, serenity, and income potential in South Maui. This rare second-floor 1-bedroom, 2-bathroom condominium is your gateway to breathtaking sunsets and front-row whale

  Shelley Hefner Coldwell Banker Island Prop(S)

  3600 Wailea Alanui Dr Unit 2012, Kihei, HI 96753
• 

  

  /50

  $1,600,000

  Sold Oct 31, 2025

  71 Wailea Gateway Place Unit 7-104, Kihei, HI 96753

  • 3 Beds
  • 2 Baths
  • 1,312 Sq Ft
  • Built 2018

  Last Sold Summary

  • 16% Below List Price
  • $1,220/SF
  • 46 Days On Market

  Current Estimated Value $1,670,754

  Last Listing Agent Randolph Antonio Keller Williams Realty Maui-Ka

  71 Wailea Gateway Place Unit 7-104, Kihei, HI 96753
• 

  

  /40

  Est $1,196,022

  Not Listed For Sale

  155 Wailea Ike Place Unit 16, Kihei, HI 96753

  • 2 Beds
  • 2 Baths
  • 1,148 Sq Ft
  • Built 1990

  155 Wailea Ike Place Unit 16, Kihei, HI 96753

  Last Sold Summary

  • 53 Days On Market
• 

  

  /50

  $1,199,000

  • 1 Bed
  • 2 Baths
  • 866 Sq Ft

  10 Wailea Ekolu Place Unit 1204, Kihei, HI 96753

  Whether you're seeking a high-performing vacation rental, a lock-and-leave second home, or a comfortable full-time residence, Wailea Ekolu #1204 offers exceptional value in one of South Maui's most desirable communities. Positioned on the front row overlooking the Wailea Blue Golf Course with sweeping ocean views beyond, this beautifully updated 1-bedroom, 2-bath residence combines privacy,

  Gary Mooers Coldwell Banker Island Prop(S)

  10 Wailea Ekolu Place Unit 1204, Kihei, HI 96753
• 

  

  /42

  $516,000

  Sold May 12, 2026

  160 Keonekai Rd Unit 11-104, Kihei, HI 96753

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

  Last Sold Summary

  • 6% Below List Price
  • $688/SF
  • 27 Days On Market

  Current Estimated Value $503,826

  Last Listing Agent Todd Hudson Keller Williams Realty Maui-Ki

  160 Keonekai Rd Unit 11-104, Kihei, HI 96753
• 

  

  /49

  Est $6,145,215

  Not Listed For Sale

  3800 Wailea Alanui Dr Unit G201, Kihei, HI 96753

  • 3 Beds
  • 4 Baths
  • 2,879 Sq Ft
  • Built 2005

  3800 Wailea Alanui Dr Unit G201, Kihei, HI 96753

  Last Sold Summary

  • 560 Days On Market
• 

  

  /50

  $1,749,900

  $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
• 

  

  /50

  $2,685,000

  Sold Feb 06, 2026

  61 Kainehe Place Unit 13B, Kihei, HI 96753

  • 3 Beds
  • 3 Baths
  • 1,796 Sq Ft
  • Built 2006

  Last Sold Summary

  • 6% Below List Price
  • $1,495/SF
  • 36 Days On Market

  Current Estimated Value $2,667,249

  Last Listing Agent Hank Rapoza Coldwell Banker Island Prop-Ku

  61 Kainehe Place Unit 13B, Kihei, HI 96753
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  /44

  Est $6,400,442

  Not Listed For Sale

  Unlisted Address

  • 3 Beds
  • 3 Baths
  • 467,834 Sq Ft
  • Built 2005

  Unlisted Address

  Last Sold Summary

  • 40 Days On Market
• 

  

  /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

  Alex Iskenderian Berkshire Hathaway Maui Prop-L

  3291 Waileia Place, Kihei, HI 96753
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  /50

  $1,550,000

  Sold May 20, 2026

  521 Kupulau Dr, Kihei, HI 96753

  • 3 Beds
  • 2 Baths
  • 2,111 Sq Ft
  • Built 1974

  Last Sold Summary

  • 35% Below List Price
  • $734/SF
  • 489 Days On Market

  Current Estimated Value $1,958,474

  Last Listing Agent Nancy Nevius Coldwell Banker Island Prop(S)

  521 Kupulau Dr, Kihei, HI 96753
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  /35

  Est $4,682,411

  Not Listed For Sale

  3800 Wailea Alanui Dr Unit 404, Kihei, HI 96753

  • 2 Beds
  • 2 Baths
  • 1,978 Sq Ft
  • Built 2005

  3800 Wailea Alanui Dr Unit 404, Kihei, HI 96753

  Last Sold Summary

  • 316 Days On Market
• 

  

  /14

  $399,000

  • 1 Bed
  • 1 Bath
  • 597 Sq Ft

  2747 S Kihei Rd Unit A101, Kihei, HI 96753

  Kihei Shores A101 is the least expensive fee simple condo in Kihei at the time of this listing. This one bedroom one bath unit is located just a short walk to Kamaole III beach park. Enjoy the garden view and a peek of ocean from the living room. Kihei Shores is conveniently located to shopping, dining, and several wonderful beach parks. The complex offers a pool, spa, BBQ areas and surfboard

  Leslie Smith Hawaii Life (W)

  2747 S Kihei Rd Unit A101, Kihei, HI 96753
• 

  

  /50

  $2,700,000

  Sold Jan 02, 2026

  153 Hokai Place, Kihei, HI 96753

  • 5 Beds
  • 3 Baths
  • 3,175 Sq Ft
  • Built 2004

  Last Sold Summary

  • 10% Below List Price
  • $850/SF
  • 25 Days On Market

  Current Estimated Value $2,755,702

  Last Listing Agent Lydia Pedro Hawaii Life (W)

  153 Hokai Place, Kihei, HI 96753
• 

  

  /30

  Est $5,782,440

  Not Listed For Sale

  3800 Wailea Alanui Dr Unit 312, Kihei, HI 96753

  • 3 Beds
  • 3 Baths
  • 467,834 Sq Ft
  • Built 2005

  3800 Wailea Alanui Dr Unit 312, Kihei, HI 96753

  Last Sold Summary

  • 260 Days On Market
• 

  

  /43

  $754,000

  • 1 Bed
  • 2 Baths
  • 849 Sq Ft

  2777 S Kihei Rd Unit 107, Kihei, HI 96753

  Situated in South Kihei’s premier resort community, Maui Kamaole, this spacious 1-bedroom, 2-bath condo offers a perfect blend of comfort, privacy, and convenience. Located on 23 acres of lush tropical landscaping directly across from Kamaole Beach Park III, this unit feels like a private oasis yet is just minutes from Wailea’s top golf, dining, and shopping. The downstairs condo is exceptionally

  Ron Silva Island Sotheby's International Realty(M)

  2777 S Kihei Rd Unit 107, Kihei, HI 96753
• 

  

  /40

  $1,320,000

  Sold Feb 11, 2026

  2757 S Kihei Rd Unit 403, Kihei, HI 96753

  • 3 Beds
  • 2 Baths
  • 1,389 Sq Ft
  • Built 2023

  Last Sold Summary

  • 16% Below List Price
  • $950/SF
  • 370 Days On Market

  Current Estimated Value $1,276,010

  Last Listing Agent Matthew Tarasenko PMI Maui

  2757 S Kihei Rd Unit 403, Kihei, HI 96753
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  /50

  Est $3,782,759

  Not Listed For Sale

  3800 Wailea Alanui Dr Unit 106, Kihei, HI 96753

  • 2 Beds
  • 2 Baths
  • 1,899 Sq Ft
  • Built 2005

  3800 Wailea Alanui Dr Unit 106, Kihei, HI 96753

  Last Sold Summary

  • 49 Days On Market
• 

  

  /40

  $2,100,000

  $150K PRICE DROP

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

  63 Wailea Gateway Place Unit 5-103, Kihei, HI 96753

  Keala O Wailea 5-103 offers panoramic Pacific Ocean views from one of Wailea's premier hillside communities. This single-level 2-bedroom, 2-bathroom residence spans approximately 1,248 square feet and was built in 2018, with updates completed in 2025. Retractable glass doors frame sweeping ocean vistas and create seamless indoor-outdoor living. The open-concept layout positions the living area,

  Stacy Levin Coldwell Banker Island Prop(S)

  63 Wailea Gateway Place Unit 5-103, Kihei, HI 96753
• 

  

  /41

  $800,000

  Sold Nov 04, 2025

  155 Wailea Ike Place Unit 67, Kihei, HI 96753

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

  Last Sold Summary

  • 26% Below List Price
  • $881/SF
  • 342 Days On Market

  Current Estimated Value $1,182,020

  Last Listing Agent Patrick Franta Coldwell Banker Island Prop(S)

  155 Wailea Ike Place Unit 67, Kihei, HI 96753
• 

  

  /49

  Est $1,346,117

  Not Listed For Sale

  3150 Wailea Alanui Dr Unit 3706, Kihei, HI 96753

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

  3150 Wailea Alanui Dr Unit 3706, Kihei, HI 96753

  Last Sold Summary

  • 25 Days On Market
• 

  

  /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
• 

  

  /33

  $980,000

  Sold Feb 06, 2026

  10 Wailea Ekolu Place Unit 408, Kihei, HI 96753

  • 1 Bed
  • 2 Baths
  • 866 Sq Ft
  • Built 1979

  Last Sold Summary

  • 2% Below List Price
  • $1,132/SF
  • 8 Days On Market

  Current Estimated Value $1,178,317

  Last Listing Agent David McAlear Coldwell Banker Island Prop-Ku

  10 Wailea Ekolu Place Unit 408, Kihei, HI 96753
• 

  

  /31

  Est $2,036,724

  Not Listed For Sale

  3150 Wailea Alanui Dr Unit 3201, Kihei, HI 96753

  • 2 Beds
  • 2.5 Baths
  • 631,620 Sq Ft
  • Built 1992

  3150 Wailea Alanui Dr Unit 3201, Kihei, HI 96753

  Last Sold Summary

  • 2 Days On Market
• 

  

  /14

  $395,000

  • 1 Bed
  • 1 Bath
  • 597 Sq Ft

  2747 S Kihei Rd Unit A302, Kihei, HI 96753

  Coastal Living right across the street from Kamaole III Beach Park! Welcome home to your slice of South Maui paradise! This desirable 1-bedroom, 1-bathroom condo at Kihei Shores offers the ultimate blend of convenience and relaxed island living. Tucked peacefully away from the main road traffic, this 597 sq. ft. unit features an open floor plan, a private covered lanai perfect for morning coffee,

  Marnel Lozano Destination Maui Realty LLC

  2747 S Kihei Rd Unit A302, Kihei, HI 96753
• 

  

  /48

  $2,500,000

  Sold Jul 09, 2025

  134 Kainui Loop Unit 66A, Kihei, HI 96753

  • 3 Beds
  • 3 Baths
  • 1,796 Sq Ft
  • Built 2006

  Last Sold Summary

  • 4% Below List Price
  • $1,392/SF
  • 9 Days On Market

  Current Estimated Value $2,538,296

  Last Listing Agent Sara Romvari Romvari Realty Ltd

  134 Kainui Loop Unit 66A, Kihei, HI 96753
• 

  

  /43

  Est $2,433,217

  Not Listed For Sale

  3150 Wailea Alanui Dr Unit 3106, Kihei, HI 96753

  • 2 Beds
  • 3 Baths
  • 1,699 Sq Ft
  • Built 1992

  3150 Wailea Alanui Dr Unit 3106, Kihei, HI 96753

  Last Sold Summary

  • 142 Days On Market
• 

  

  /25

  $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
• 

  

  /47

  $2,075,000

  Sold Jul 16, 2025

  2841 Umalu Place, Kihei, HI 96753

  • 5 Beds
  • 4 Baths
  • 2,800 Sq Ft
  • Built 1988

  Last Sold Summary

  • 17% Below List Price
  • $741/SF
  • 489 Days On Market

  Current Estimated Value $2,022,139

  Last Listing Agent Brandy Shelby Westminster Realty Inc

  2841 Umalu Place, Kihei, HI 96753
• 

  

  /50

  Est $2,065,613

  Not Listed For Sale

  3150 Wailea Alanui Dr Unit 2804, Kihei, HI 96753

  • 2 Beds
  • 3 Baths
  • 1,699 Sq Ft
  • Built 1992

  3150 Wailea Alanui Dr Unit 2804, Kihei, HI 96753

  Last Sold Summary

  • 68 Days On Market
• 

  

  /43

  $1,045,000

  $350K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft

  155 Wailea Ike Place Unit 140, Kihei, HI 96753

  This lovely remodeled and cared for 2 bedroom/2 bathroom Grand Champions unit speaks of Hawaiiana and is being sold 'Turn Key' Furnished. Unit #140 is upper-level with vaulted ceilings and lives large. The sheer scale and volume of space adds a sense of elegance and comfort to the living experience. Vernal and serene truly describe the setting. There are peaceful, green and pastoral views from

  Robbie Dein Maui Real Estate Advisors LLC

  155 Wailea Ike Place Unit 140, Kihei, HI 96753
• 

  

  /26

  $475,000

  Sold Apr 21, 2026

  160 Keonekai Rd Unit 16-102, Kihei, HI 96753

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

  Last Sold Summary

  • $633/SF
  • 2 Days On Market

  Current Estimated Value $506,661

  Last Listing Agent Paul Ferrall Coldwell Banker Island Prop-Ku

  160 Keonekai Rd Unit 16-102, Kihei, HI 96753
• 

  

  /49

  Est $1,877,332

  Not Listed For Sale

  3150 Wailea Alanui Dr Unit 2803, Kihei, HI 96753

  • 2 Beds
  • 2 Baths
  • 1,692 Sq Ft
  • Built 1992

  3150 Wailea Alanui Dr Unit 2803, Kihei, HI 96753

  Last Sold Summary

  • 175 Days On Market
• 

  

  /32

  $699,900

  • 2 Beds
  • 2 Baths
  • 1,115 Sq Ft

  2881 S Kihei Rd Unit 100, Kihei, HI 96753

  Well kept and nicely appointed vacation rental located near the top of the complex. This is a very spacious 2 bed, 2 bath with an open floor plan that appeals to visitors. The south Maui location offers restaurants, shopping, resort golf courses and beautiful beaches in close proximity to the condo. Call your favorite REALTOR® to schedule a private showing today. This is a Leasehold property.

  Roger Pleski Coldwell Banker Island Prop(S)

  2881 S Kihei Rd Unit 100, Kihei, HI 96753

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