Wailea, HI Homes

• 

  

  

  /50

  $3,200,000

  $300K PRICE DROP

  • 4 Beds
  • 4 Baths
  • 3,399 Sq Ft

  744 Lanina Place, Kihei, HI 96753

  Eclectic, exotic, bursting with energy this Maui Meadows home is such a special spot on the island with its breathtaking ocean views, deep tropical setting and exquisite finishes throughout. You will be Awestruck with the incredible design and finishes throughout this entire property with the beautiful pool, ideally situated for entertaining, lavish master suite and incredible chef’s kitchen.

  Tom Tezak Hawaii Life (W)

  744 Lanina Place, Kihei, HI 96753
• 

  

  

  /23

  $3,650 Per Month

  • 2 Beds
  • 2 Baths
  • 949 Sq Ft
  • Wailea Fairway Villas 2 bedroom 2 bath furnished upstairs unit

  3950 Kalai Waa St, Wailea-Makena, HI 96753

  Wailea Fairway Villas - 2 bedroom 2 bath nicely furnished upstairs unit. This property is located on the Wailea Blue Golf Course and has a pool, Jacuzzi, barbecue and gym. Close to beautiful beaches, great shopping and restaurants. Washer and dryer in unit, dishwasher, split AC system.Two parking stalls - one assigned, one unassigned. Rent - $3,650/mo. plus GET

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

  

  

  /50

  $950,000

  Sold Feb 20, 2026

  3300 Wailea Alanui Dr Unit 20D, Kihei, HI 96753

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

  Last Sold Summary

  • 17% Below List Price
  • $998/SF
  • 98 Days On Market

  Current Estimated Value $1,014,892

  Last Listing Agent Robbie Dein Maui Real Estate Advisors LLC

  3300 Wailea Alanui Dr Unit 20D, Kihei, HI 96753
• 

  

  

  /32

  Est $570,131

  Not Listed For Sale

  160 Keonekai Rd Unit 4-202, Kihei, HI 96753

  • 2 Beds
  • 2 Baths
  • 673,002 Sq Ft
  • Built 1992

  160 Keonekai Rd Unit 4-202, Kihei, HI 96753

  Last Sold Summary

  • 21 Days On Market
• 

  

  

  /48

  $5,900,000

  $995K PRICE DROP Pending

  • 3 Beds
  • 3 Baths
  • 1,961 Sq Ft

  3800 Wailea Alanui Dr Unit 503, Kihei, HI 96753

  Enormous Ocean and Outer Island Views from this stunning, rarely available TOP FLOOR 3bedroom/3bathroom fully furnished Penthouse at Wailea Beach Villas. A tranquil, remodeled, and spacious turnkey offering boasting dramatic views, seamless indoor and outdoor living on a large entertaining lanai and unique materials and upgrades throughout. The open kitchen is equipped with New granite

  Meghan Clair Coldwell Banker Island Prop(S)

  3800 Wailea Alanui Dr Unit 503, Kihei, HI 96753
• 

  

  /29

  $5,950 Per Month

  • 3 Beds
  • 3 Baths
  • 1,568 Sq Ft
  • Wailea Fairway Villas Townhome With Ocean, Golf Course and Mountain Views

  3950 Kalai Waa St Unit V-101, Kihei, 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, Kihei, HI 96753
• 

  

  /43

  $3,276,000

  Sold Feb 23, 2026

  4000 Wailea Alanui Dr Unit 2003, Kihei, HI 96753

  • 2 Beds
  • 3 Baths
  • 1,584 Sq Ft
  • Built 1987

  Last Sold Summary

  • 14% Below List Price
  • $2,068/SF
  • 58 Days On Market

  Current Estimated Value $3,281,282

  Last Listing Agent Debbie Arakaki Compass

  4000 Wailea Alanui Dr Unit 2003, Kihei, HI 96753
• 

  

  /49

  Est $4,174,305

  Not Listed For Sale

  3100 Wailea Alanui Dr Unit 21, Kihei, HI 96753

  • 3 Beds
  • 4 Baths
  • 2,386 Sq Ft
  • Built 2008

  3100 Wailea Alanui Dr Unit 21, Kihei, HI 96753

  Last Sold Summary

  • 30 Days On Market
• 

  

  /43

  $685,000

  • 1 Bed
  • 1 Bath
  • 778 Sq Ft

  2737 S Kihei Rd Unit 142, Kihei, HI 96753

  Hale Kamaole 142 is a beautifully remodeled ground floor 1-bedroom, 1-bath condo that delivers a fresh, modern beach vibe just steps from Kamaole Beach Park III and the upper pool. Come experience a true “WOW” with luxury furnishings, cool tile flooring, and a bright open-concept layout that feels larger than a typical one bedroom. The kitchen has been thoughtfully redesigned to create a more

  Clint Hansen Maui Luxury Real Estate LLC

  2737 S Kihei Rd Unit 142, Kihei, HI 96753
• 

  

  /33

  $2,950 Per Month

  • 2 Beds
  • 1.5 Baths
  • 750 Sq Ft
  • Keonekai Villages Furnished Upstairs 2 bedroom, 1.5 bathroom unit, with 2 parking spaces

  160 Keonekai Rd Unit 25-202, Kihei, HI 96753

  Renovated and furnished 2BR, 1.5BA top floor unit with A/C, washer/dryer in unit, lighted ceiling fans, security screen door, granite counter tops, tile and wood floors and newer appliances. 2 Assigned tandem parking spaces, one covered and one uncovered. Very nice Haleakala views from your private top story lanai. Water, sewer, basic cable, internet & standard trash removal is included

  160 Keonekai Rd Unit 25-202, Kihei, HI 96753
• 

  

  /49

  $487,000

  Sold Sep 18, 2025

  2747 S Kihei Rd Unit J206, Kihei, HI 96753

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

  Last Sold Summary

  • 1% Below List Price
  • $664/SF
  • 14 Days On Market

  Current Estimated Value $481,203

  Last Listing Agent Judy Boyd Equity Hawaii Real Estate LLC

  2747 S Kihei Rd Unit J206, Kihei, HI 96753
• 

  

  /37

  Not Listed For Sale

  2695 S Kihei Rd Unit 5-313, Kihei, HI 96753

  • 1 Bed
  • 2 Baths
  • 818 Sq Ft
  • Built 1983

  2695 S Kihei Rd Unit 5-313, Kihei, HI 96753

  Last Sold Summary

  • 104 Days On Market
• 

  

  /50

  $2,875,000

  • 2 Beds
  • 2 Baths
  • 1,374 Sq Ft

  60 Kai Malu Dr Unit 201 (11C), Kihei, HI 96753

  The One You’ve Been Waiting For! This pristine, second floor 2 Bedroom 2 Bath unit in Wailea’s Newest Development has it all. This premium location provides you with amazing Ocean and Outer Island views with incredible sunsets and the indescribable joy of great whale watching from your new home. La’i Loa 11C features an open floor plan that sits wide to the view for maximum enjoyment throughout

  Dale Richardson Hawaii Life (W)

  60 Kai Malu Dr Unit 201 (11C), Kihei, HI 96753
• 

  

  /39

  $6,700 Per Month

  • 2 Beds
  • 2 Baths
  • 1,375 Sq Ft
  • Luxury Wailea Retreat in La’i Loa Villas

  36 Kai Malu Dr, Kihei, HI 96753

  Luxury resort-style living at La’i Loa Villas in Wailea. This brand-new, stunning 2-bedroom, 2-bathroom condo is located in a boutique building and offers 1,375 sq. ft. of beautifully designed interior space. A dramatic sliding glass door creates effortless indoor-outdoor living and opens to a generous 350 sq. ft. lanai with an outdoor wet bar and built-in BBQ, perfect for entertaining while

  36 Kai Malu Dr, Kihei, HI 96753
• 

  

  /47

  $6,600,000

  Sold Mar 16, 2026

  192 Halau Place, Kihei, HI 96753

  • 3 Beds
  • 4 Baths
  • 3,808 Sq Ft
  • Built 1987

  Last Sold Summary

  • 12% Below List Price
  • $1,733/SF
  • 93 Days On Market

  Current Estimated Value $6,974,491

  Last Listing Agent David Richardson Hawaii Life (W)

  192 Halau Place, Kihei, HI 96753
• 

  

  /45

  Est $603,215

  Not Listed For Sale

  160 Keonekai Rd Unit 10-104, Kihei, HI 96753

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

  160 Keonekai Rd Unit 10-104, Kihei, HI 96753

  Last Sold Summary

  • 17 Days On Market
• 

  

  /46

  $17,950,000

  $3M PRICE DROP

  • 4 Beds
  • 5 Baths
  • 4,328 Sq Ft

  4950 Makena Rd Unit 8, Kihei, HI 96753

  Nestled into a gated residential condominium community on Maui’s sun-drenched south shore, this 4-bedroom, 4.5-bath home provides over 4,300 sq.ft of interior space, beautifully renovated in 2024. This home offers stunning sunset views year-round. The updated kitchen has a substantial two-level island with Patagonia quartzite countertops and bar seating for six, with Leicht cabinetry, tile

  Leslie Smith Hawaii Life (W)

  4950 Makena Rd Unit 8, Kihei, HI 96753
• 

  

  /24

  $6,500 Per Month

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Keala O Wailea, Wailea Gateway

  71 Wailea Gateway Place, Kihei, HI 96753

  Welcome to Keala O Wailea, one of Wailea’s most desirable gated condominium communities, offering a refined blend of modern design, convenience, and island luxury. Completed in 2018, this beautifully maintained ground-floor residence features 2 bedrooms and 2 bathrooms, with approximately 1,200 square feet of interior living space plus an additional covered lanai of about 200 square

  71 Wailea Gateway Place, Kihei, HI 96753
• 

  $1,375,000

  Sold Aug 18, 2025

  2777 S Kihei Rd Unit 205, Kihei, HI 96753

  • 2 Beds
  • 2 Baths
  • 1,214 Sq Ft
  • Built 1998

  Last Sold Summary

  • 19% Below List Price
  • $1,133/SF
  • 215 Days On Market

  Current Estimated Value $1,028,537

  Last Listing Agent Matthew Iannaccio eXp Realty

  2777 S Kihei Rd Unit 205, Kihei, HI 96753
• 

  

  /50

  Not Listed For Sale

  2695 S Kihei Rd Unit 10-108, Kihei, HI 96753

  • 1 Bed
  • 2 Baths
  • 818 Sq Ft
  • Built 1983

  2695 S Kihei Rd Unit 10-108, Kihei, HI 96753

  Last Sold Summary

  • 6 Days On Market
• 

  

  /50

  $2,489,000

  • 3 Beds
  • 3 Baths
  • 1,852 Sq Ft

  115 Kai La Place Unit 36A, Kihei, HI 96753

  Experience luxury living at 115 Kai La Place, Kai Malu Maui. This beautifully remodeled furnished 3 bedroom, 2.5-bath residence features a primary suite on the first floor and a refined modern interior. Recent upgrades include new designer appliances, flooring, cabinetry and countertops throughout. Energy-efficient with 19 owned PV solar panels and a Tesla battery. The tasteful design and

  Carol Olsen Coldwell Banker Island Prop(S)

  115 Kai La Place Unit 36A, Kihei, HI 96753
• 

  

  /52

  $11,500 Per Month

  • 3 Beds
  • 3 Baths
  • 1,742 Sq Ft
  • Wailea's newest development, La'i Loa, 3 bedroom / 3 bathroom Furnished & Fabulous - Fall/Winter ...

  30 Kai Malu Dr Unit 101, Kihei, HI 96753

  Introducing a rare opportunity at Wailea's newest development, La'i Loa. A serene brand new 3 bedroom / 3 bathroom retreat embracing island elegance with modern grace. The expansive sliding window wall in the great room offers generous indoor outdoor living with mesmerizing views from the ocean-facing lanai. This conveniently located villa offers everything you need for a gratifying lifestyle at

  30 Kai Malu Dr Unit 101, Kihei, HI 96753
• 

  

  /35

  $1,650,000

  Sold Dec 24, 2025

  71 Wailea Gateway Place Unit 7-203, Kihei, HI 96753

  • 2 Beds
  • 2 Baths
  • 1,241 Sq Ft
  • Built 2018

  Last Sold Summary

  • 6% Below List Price
  • $1,330/SF
  • 148 Days On Market

  Current Estimated Value $1,643,043

  Last Listing Agent Marcus Nygren Coldwell Banker Island Prop(S)

  71 Wailea Gateway Place Unit 7-203, Kihei, HI 96753
• 

  

  /50

  Est $4,187,076

  Not Listed For Sale

  3100 Wailea Alanui Dr Unit 6, Kihei, HI 96753

  • 3 Beds
  • 4 Baths
  • 2,386 Sq Ft
  • Built 2008

  3100 Wailea Alanui Dr Unit 6, Kihei, HI 96753

  Last Sold Summary

  • 213 Days On Market
• 

  

  /37

  $1,550,000

  $225K 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
• 

  

  /50

  $1,950,000

  Sold Mar 09, 2026

  126 Ponana St, Kihei, HI 96753

  • 3 Beds
  • 3 Baths
  • 1,762 Sq Ft
  • Built 1997

  Last Sold Summary

  • 13% Below List Price
  • $1,107/SF
  • 174 Days On Market

  Current Estimated Value $1,970,207

  Last Listing Agent Dennis Rush Compass-W

  126 Ponana St, Kihei, HI 96753
• 

  

  /50

  Est $1,167,989

  Not Listed For Sale

  2757 S Kihei Rd Unit 702, Kihei, HI 96753

  • 2 Beds
  • 2 Baths
  • 1,251 Sq Ft
  • Built 2023

  2757 S Kihei Rd Unit 702, Kihei, HI 96753

  Last Sold Summary

  • 3 Days On Market
• 

  

  /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
• 

  

  /49

  $2,795,000

  Sold Dec 24, 2025

  371 Pualoa Nani Place Unit Lot 24, Kihei, HI 96753

  • 3 Beds
  • 3 Baths
  • 2,354 Sq Ft
  • Built 2000

  Last Sold Summary

  • $1,187/SF
  • 23 Days On Market

  Current Estimated Value $2,686,557

  Last Listing Agent Christine Warner Coldwell Banker Island Prop(S)

  371 Pualoa Nani Place Unit Lot 24, Kihei, HI 96753
• 

  

  /44

  Not Listed For Sale

  2695 S Kihei Rd Unit 3-202, Kihei, HI 96753

  • 1 Bed
  • 2 Baths
  • 653,400 Sq Ft
  • Built 1983

  2695 S Kihei Rd Unit 3-202, Kihei, HI 96753

  Last Sold Summary

  • 5 Days On Market
• 

  

  /50

  $1,875,000

  $324K 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
• 

  

  /50

  $2,235,000

  Sold Dec 12, 2025

  904 Kupulau Dr, Kihei, HI 96753

  • 3 Beds
  • 5 Baths
  • 4,220 Sq Ft
  • Built 1989

  Last Sold Summary

  • 26% Below List Price
  • $530/SF
  • 363 Days On Market

  Current Estimated Value $2,928,178

  Last Listing Agent Todd Hudson Keller Williams Realty Maui-Ki

  904 Kupulau Dr, Kihei, HI 96753
• 

  

  /34

  Est $2,153,285

  Not Listed For Sale

  68 Poailani Place Unit 35, Kihei, HI 96753

  • 4 Beds
  • 5 Baths
  • 2,175 Sq Ft
  • Built 2006

  68 Poailani Place Unit 35, Kihei, HI 96753

  Last Sold Summary

  • 39 Days On Market
• 

  

  /50

  $750,000

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

  2881 S Kihei Rd Unit 33, Kihei, HI 96753

  This ground floor 2-bedroom, 2-bath condo checks all the boxes—ocean views, a spacious layout, and one of the best locations in South Kihei. Step out onto your large front lanai (accessible from both the living room and primary bedroom) and take in the tropical setting with a peek of the Pacific—it’s the perfect spot for morning coffee or sunset cocktails. Inside, you’ll find an open, comfortable

  Josh Feyen Real Broker

  2881 S Kihei Rd Unit 33, Kihei, HI 96753
• 

  

  /50

  $3,850,000

  Sold Mar 27, 2026

  52 Kai Malu Dr Unit 101 (9A), Kihei, HI 96753

  • 3 Beds
  • 3 Baths
  • 1,742 Sq Ft
  • Built 2024

  Last Sold Summary

  • $2,210/SF
  • 0 Days On Market

  Last Listing Agent Carla Lorimor Polaris Pacific

  52 Kai Malu Dr Unit 101 (9A), Kihei, HI 96753
• 

  

  /3

  Est $34,602,644

  Not Listed For Sale

  47 Malukai Ln Unit 13, Kihei, HI 96753

  • 3 Beds
  • 4 Baths
  • 4,762 Sq Ft
  • Built 2013

  47 Malukai Ln Unit 13, Kihei, HI 96753

  Last Sold Summary

  • 0 Days On Market
• 

  

  /41

  $4,300,000

  $2M PRICE DROP

  • 3 Beds
  • 4 Baths
  • 2,419 Sq Ft

  4000 Wailea Alanui Dr Unit 2502, Kihei, HI 96753

  OUTSTANDING VALUE for one of Wailea Point's most FABULOUS VIEW UNITS. This is the highly sought after Upper Level D plan, Wailea Point’s second largest standard floor plan located on the top 2 floors of a 4-story building; 2 levels, 3 bedrooms, 4 bathrooms. The location is a “10”, affording spectacular ocean views. The vaulted ceilings are a bonus, and new windows were installed in 2022,

  Dave Wagner Wailea Point Realty, Inc.

  4000 Wailea Alanui Dr Unit 2502, Kihei, HI 96753
• 

  

  /50

  $4,600,000

  Sold Feb 04, 2026

  4400 Makena Rd Unit 604, Kihei, HI 96753

  • 2 Beds
  • 2 Baths
  • 1,303 Sq Ft
  • Built 1981

  Last Sold Summary

  • 5% Below List Price
  • $3,530/SF
  • 68 Days On Market

  Current Estimated Value $4,503,920

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

  4400 Makena Rd Unit 604, Kihei, HI 96753
• 

  

  /45

  Est $2,631,755

  Not Listed For Sale

  14 Kainui Loop Unit 75A, Kihei, HI 96753

  • 3 Beds
  • 2.5 Baths
  • 1,089,000 Sq Ft
  • Built 2007

  14 Kainui Loop Unit 75A, Kihei, HI 96753

  Last Sold Summary

  • 20 Days On Market
• 

  

  /46

  $2,225,000

  $100K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,360 Sq Ft

  3386 E Lani Ikena Way, Kihei, HI 96753

  Set within the prestigious Wailea Pualani Estates, this 3-bedroom, 2.5-bath residence with an additional office/media room offers refined island living with a seamless indoor-outdoor flow. The private backyard is designed for entertaining, featuring a saline heated pool with waterfall features, surrounded by lush, mature landscaping. The ocean-view primary suite includes a private lanai, creating

  Jesseca Curry Compass-W

  3386 E Lani Ikena Way, Kihei, HI 96753

Showing Results 81 - 120, Page 3 of 18