Wailea, HI Homes

• 

  

  

  /41

  Est $2,466,172

  Not Listed For Sale

  1001 Kupulau Dr, Kihei, HI 96753

  • 4 Beds
  • 4 Baths
  • 3,062 Sq Ft
  • Built 1978

  1001 Kupulau Dr, Kihei, HI 96753

  Last Sold Summary

  • 273 Days On Market

  Last Listing Agent Bob Hansen Maui Luxury Real Estate LLC
• 

  

  

  /48

  $2,250,000

  $250K PRICE DROP

  • 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
• 

  

  

  /35

  $925,000

  Sold Jan 02, 2026

  3200 Wailea Alanui Dr Unit 1803, Kihei, HI 96753

  • 1 Bed
  • 2 Baths
  • 1,022 Sq Ft
  • Built 1992

  Last Sold Summary

  • 5% Below List Price
  • $905/SF
  • 130 Days On Market

  Current Estimated Value $1,210,070

  Last Listing Agent Katherine Bryndle Berkshire Hathaway Maui Prop-W

  3200 Wailea Alanui Dr Unit 1803, Kihei, HI 96753
• 

  

  

  /50

  Est $2,592,202

  Not Listed For Sale

  738 Lanina Place, Kihei, HI 96753

  • 3 Beds
  • 3 Baths
  • 2,910 Sq Ft
  • Built 2000

  738 Lanina Place, Kihei, HI 96753

  Last Sold Summary

  • 102 Days On Market

  Last Listing Agent Dennis Rush Compass-W
• 

  

  

  /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
• 

  

  /50

  $2,202,022

  Sold Oct 08, 2025

  736 Mililani Place, Kihei, HI 96753

  • 3 Beds
  • 3 Baths
  • 2,000 Sq Ft
  • Built 1999

  Last Sold Summary

  • 37% Below List Price
  • $1,101/SF
  • 289 Days On Market

  Current Estimated Value $2,342,638

  Last Listing Agent Steve Landin Keller Williams Realty Maui-Ka

  736 Mililani Place, Kihei, HI 96753
• 

  

  /30

  Est $2,385,804

  Not Listed For Sale

  1108 Kupulau Dr, Kihei, HI 96753

  • 3 Beds
  • 2 Baths
  • 2,820 Sq Ft
  • Built 1975

  1108 Kupulau Dr, Kihei, HI 96753

  Last Sold Summary

  • 119 Days On Market

  Last Listing Agent Christopher Barca Compass-W
• 

  

  /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
• 

  

  /34

  $475,000

  Sold Dec 10, 2025

  160 Keonekai Rd Unit 18-204, Kihei, HI 96753

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

  Last Sold Summary

  • 9% Below List Price
  • $633/SF
  • 83 Days On Market

  Current Estimated Value $491,458

  Last Listing Agent Sara Fox Keller Williams Realty Maui-Ki

  160 Keonekai Rd Unit 18-204, Kihei, HI 96753
• 

  

  /50

  Est $2,109,335

  Not Listed For Sale

  754 Kumulani Dr, Kihei, HI 96753

  • 3 Beds
  • 2 Baths
  • 1,964 Sq Ft
  • Built 1976

  754 Kumulani Dr, Kihei, HI 96753

  Last Sold Summary

  • 63 Days On Market

  Last Listing Agent Darla Phillips eXp Realty
• 

  

  /50

  $3,785,000

  $110K PRICE DROP

  • 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
• 

  

  /38

  $509,000

  Sold Jan 09, 2026

  2747 S Kihei Rd Unit B101, Kihei, HI 96753

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

  Last Sold Summary

  • 4% Below List Price
  • $708/SF
  • 45 Days On Market

  Current Estimated Value $476,298

  Last Listing Agent Kelly Swanson Compass-W

  2747 S Kihei Rd Unit B101, Kihei, HI 96753
• 

  

  /50

  Est $2,601,199

  Not Listed For Sale

  595 Kupulau Dr, Kihei, HI 96753

  • 4 Beds
  • 4 Baths
  • 3,128 Sq Ft
  • Built 1974

  595 Kupulau Dr, Kihei, HI 96753

  Last Sold Summary

  • 11 Days On Market

  Last Listing Agent Geoffrey Cook Century 21 Island Homes
• 

  

  /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

  $2,750,000

  Sold Oct 01, 2025

  333 Kai Malu Place Unit 58A, Kihei, HI 96753

  • 3 Beds
  • 3 Baths
  • 1,796 Sq Ft
  • Built 2007

  Last Sold Summary

  • 13% Below List Price
  • $1,531/SF
  • 159 Days On Market

  Current Estimated Value $2,571,877

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

  333 Kai Malu Place Unit 58A, Kihei, HI 96753
• 

  Est $1,711,486

  Not Listed For Sale

  3038 Mapu Place, Kihei, HI 96753

  • 3 Beds
  • 2 Baths
  • 1,848 Sq Ft
  • Built 1977

  3038 Mapu Place, Kihei, HI 96753

  Last Sold Summary

  • 251 Days On Market

  Last Listing Agent Yvienne Peterson Drop - 2024
• 

  

  /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
• 

  

  /44

  $1,875,000

  Sold Nov 21, 2025

  147 Ponana St, Kihei, HI 96753

  • 3 Beds
  • 2 Baths
  • 1,988 Sq Ft
  • Built 1996

  Last Sold Summary

  • 4% Below List Price
  • $943/SF
  • 4 Days On Market

  Current Estimated Value $1,838,457

  Last Listing Agent Jean Keating Coldwell Banker Island Prop-Ku

  147 Ponana St, Kihei, HI 96753
• 

  

  /50

  Est $3,169,767

  Not Listed For Sale

  3366 Kehala Dr, Kihei, HI 96753

  • 4 Beds
  • 5 Baths
  • 3,535 Sq Ft
  • Built 1978

  3366 Kehala Dr, Kihei, HI 96753

  Last Sold Summary

  • 31 Days On Market

  Last Listing Agent Clint Hansen Maui Luxury Real Estate LLC
• 

  

  /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
• 

  

  /30

  $12,900,000

  Sold Aug 22, 2025

  4000 Wailea Alanui Dr Unit 102, Kihei, HI 96753

  • 3 Beds
  • 3 Baths
  • 3,850 Sq Ft
  • Built 1986

  Last Sold Summary

  • 11% Below List Price
  • $3,351/SF
  • 260 Days On Market

  Current Estimated Value $8,304,117

  Last Listing Agent Dave Wagner Wailea Point Realty, Inc.

  4000 Wailea Alanui Dr Unit 102, Kihei, HI 96753
• 

  

  /50

  Est $2,620,123

  Not Listed For Sale

  3476 Akala Dr, Kihei, HI 96753

  • 4 Beds
  • 4 Baths
  • 4,312 Sq Ft
  • Built 1986

  3476 Akala Dr, Kihei, HI 96753

  Last Sold Summary

  • 160 Days On Market

  Last Listing Agent Alex Abreu Hawaii Life (W)
• 

  

  /32

  $1,275,000

  $74K PRICE DROP

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

  3200 Wailea Alanui Dr Unit 1605, Kihei, HI 96753

  Enjoy the Wailea lifestyle from this ground-floor, fee-simple 2-bedroom, 2-bath condominium at The Palms at Wailea, one of the most affordable fee-simple, vacation-rentable two-bedroom condominiums currently available in Wailea. Just a short walk to Keawakapu Beach Park and the Wailea Beach Path, and minutes from The Shops at Wailea, championship golf, tennis, luxury resorts, spas, and

  Kathleen Tezak Island Sotheby's International Realty(W)

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

  

  /36

  $1,875,000

  Sold Mar 17, 2026

  758 Lanina Place, Kihei, HI 96753

  • 3 Beds
  • 3 Baths
  • 2,344 Sq Ft
  • Built 1977

  Last Sold Summary

  • 6% Below List Price
  • $800/SF
  • 128 Days On Market

  Current Estimated Value $2,085,625

  Last Listing Agent Chana Boone The Agency Maui

  758 Lanina Place, Kihei, HI 96753
• 

  

  /43

  Est $4,312,178

  Not Listed For Sale

  4400 Makena Rd Unit 706, Kihei, HI 96753

  • 2 Beds
  • 2 Baths
  • 1,236 Sq Ft
  • Built 1982

  4400 Makena Rd Unit 706, Kihei, HI 96753

  Last Sold Summary

  • 170 Days On Market

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

  

  /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
• 

  

  /37

  $985,000

  Sold Jun 03, 2026

  2777 S Kihei Rd Unit 202, Kihei, HI 96753

  • 2 Beds
  • 2 Baths
  • 1,052 Sq Ft
  • Built 1988

  Last Sold Summary

  • 15% Below List Price
  • $936/SF
  • 240 Days On Market

  Current Estimated Value $972,827

  Last Listing Agent Candace Horton Maui Paradise Properties LLC

  2777 S Kihei Rd Unit 202, Kihei, HI 96753
• 

  

  /50

  Est $3,744,813

  Not Listed For Sale

  4400 Makena Rd Unit 201, Kihei, HI 96753

  • 2 Beds
  • 2 Baths
  • 1,238 Sq Ft
  • Built 1981

  4400 Makena Rd Unit 201, Kihei, HI 96753

  Last Sold Summary

  • 143 Days On Market

  Last Listing Agent Don McEntire McEntire Realty
• 

  

  /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
• 

  

  /45

  $3,999,999

  Sold Jul 02, 2026

  4850 Makena Alanui Unit E205, Kihei, HI 96753

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

  Last Sold Summary

  • 11% Below List Price
  • $3,046/SF
  • 200 Days On Market

  Current Estimated Value $4,699,938

  Last Listing Agent Leslie Smith Hawaii Life (W)

  4850 Makena Alanui Unit E205, Kihei, HI 96753
• 

  

  /36

  Est $30,845,380

  Not Listed For Sale

  3200 S Kihei Rd, Kihei, HI 96753

  • 8 Beds
  • 8 Baths
  • 21,692 Sq Ft
  • Built 2002

  3200 S Kihei Rd, Kihei, HI 96753

  Last Sold Summary

  • 69 Days On Market

  Last Listing Agent Josh Jerman Hawaii Life (W)
• 

  

  /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
• 

  

  /46

  $650,000

  Sold May 15, 2026

  2695 S Kihei Rd Unit 4-301, Kihei, HI 96753

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

  Last Sold Summary

  • 14% Below List Price
  • $627/SF
  • 15 Days On Market

  Last Listing Agent Katy Foxwell Keller Williams Realty Maui-Ka

  2695 S Kihei Rd Unit 4-301, Kihei, HI 96753
• 

  

  /26

  Est $1,134,709

  Not Listed For Sale

  3950 Kalai Waa St Unit Y101, Kihei, HI 96753

  • 2 Beds
  • 2 Baths
  • 538,837 Sq Ft
  • Built 2000

  3950 Kalai Waa St Unit Y101, Kihei, HI 96753

  Last Sold Summary

  • 82 Days On Market

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

  

  /15

  $1,900,000

  • 1 Bed
  • 1 Bath
  • 596 Sq Ft

  739 Launa Dr, Kihei, HI 96753

  Exceptional opportunity to own an ocean-view property in one of South Kihei's most desirable neighborhoods. Set on a 1/2 Acre lot, 739 Launa Drive offers breathtaking Pacific Ocean views, spectacular sunsets, and the rare opportunity to create your dream Maui home in Maui Meadows. The property is improved with an existing 1-bedroom, 1-bath cottage, allowing you to enjoy the property while

  Todd Hudson Keller Williams Realty Maui-Ki

  739 Launa Dr, Kihei, HI 96753
• 

  

  /41

  $2,785,000

  Sold Oct 10, 2025

  244 Holomoana Way Unit 101 (17A), Wailea, HI 96753

  • 3 Beds
  • 3 Baths
  • 1,574 Sq Ft
  • Built 2022

  Last Sold Summary

  • 19% Below List Price
  • $1,769/SF
  • 252 Days On Market

  Last Listing Agent Carla Lorimor Polaris Pacific

  244 Holomoana Way Unit 101 (17A), Wailea, HI 96753
• 

  

  /45

  Est $1,072,844

  Not Listed For Sale

  3950 Kalai Waa St Unit S103, Kihei, HI 96753

  • 2 Beds
  • 2 Baths
  • 949 Sq Ft
  • Built 1998

  3950 Kalai Waa St Unit S103, Kihei, HI 96753

  Last Sold Summary

  • 271 Days On Market

  Last Listing Agent Bill Buffington Coldwell Banker Island Prop(S)
• 

  

  /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
• 

  

  /44

  $1,200,000

  Sold Sep 03, 2025

  2936 S Kihei Rd Unit 610, Kihei, HI 96753

  • 1 Bed
  • 2 Baths
  • 680 Sq Ft
  • Built 1975

  Last Sold Summary

  • 11% Below List Price
  • $1,765/SF
  • 61 Days On Market

  Current Estimated Value $1,126,355

  Last Listing Agent Sid Kirkland Maui Real Estate Advisors LLC

  2936 S Kihei Rd Unit 610, Kihei, HI 96753
• 

  

  /47

  Est $1,199,439

  Not Listed For Sale

  3950 Kalai Waa St Unit Q201, Kihei, HI 96753

  • 2 Beds
  • 2 Baths
  • 538,837 Sq Ft
  • Built 1998

  3950 Kalai Waa St Unit Q201, Kihei, HI 96753

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Leslie Smith Hawaii Life (W)

Showing Results 481 - 520, Page 13 of 18