Wailea, HI Homes

/50
$9,500,000
- 3 Beds
- 3 Baths
- 2,430 Sq Ft
4000 Wailea Alanui Dr Unit 1404, Kihei, HI 96753

Now offered at $9.5M, Wailea Point 1404 represents an exceptional opportunity to own one of the most beautifully renovated residences in this prestigious oceanfront community. Wailea Point 1404 is a front-row, 3 bedroom / 3 bath oceanfront masterpiece—an inspired blend of refined design, master craftsmanship, and timeless elegance in one of Maui’s most exclusive communities. Reimagined through an

Ken Smith Coldwell Banker Island Prop(S)

4000 Wailea Alanui Dr Unit 1404, Kihei, HI 96753
/34
$4,500 Per Month
- 2 Beds
- 2 Baths
- 949 Sq Ft
- Live the Wailea Lifestyle – Ocean View ground level Townhome at Wailea Fairway Villas - Seasonal ...
3950 Kalai Waa St, Wailea-Makena, HI 96753

Welcome to your Maui retreat. This beautifully furnished 2-bedroom, 2-bathroom townhome at Wailea Fairway Villas offers sweeping views of the Pacific Ocean and lush fairways of the 11th hole of Wailea Blue Golf Course.Step inside to a spacious, naturally bright, and breezy open floor plan- perfectly designed for relaxed island living. With split A/C units, you'll stay cool year-round, or

3950 Kalai Waa St, Wailea-Makena, HI 96753
/50
$2,100,000 Sold May 23, 2025

166 Heleuma Place, Kihei, HI 96753
- 3 Beds
- 2 Baths
- 2,056 Sq Ft
- Built 1988
Last Sold Summary
- 25% Below List Price
- $1,021/SF
- 103 Days On Market
Current Estimated Value $2,130,434

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

166 Heleuma Place, Kihei, HI 96753

/25
Est $1,022,490 Not Listed For Sale

700 Kupulau Dr, Kihei, HI 96753
700 Kupulau Dr, Kihei, HI 96753

Last Sold Summary
- 3% Below List Price
- $36/SF
- 7 Days On Market
- Last Sold Price $1,050,000
- Mar 04, 2025
Last Listing Agent Rick Brandt Island Sotheby's International Realty(W)

/50
$699,000
- 2 Beds
- 2 Baths
- 890 Sq Ft
2653 S Kihei Rd Unit 114, Kihei, HI 96753

Embrace the Maui lifestyle in this beautifully updated 2-bed, 2-bath, ground-level condo at Maui Parkshore 114. Directly across from the world-renowned Kamaole Beach Park III, this unit combines convenience with a welcoming atmosphere for an unforgettable island experience. Upgrades include an open, modern kitchen with sleek stainless appliances, stylish cabinetry, and elegant countertops. With

Mike Marshall Real Broker

2653 S Kihei Rd Unit 114, Kihei, HI 96753
/20
$2,550 Per Month
- 2 Beds
- 1 Bath
- 625 Sq Ft
- ***Reduced rate for the first 6 months!! $2550/month for the first 6 months - $2750/month for the...
160 Keonekai Rd Unit 14-205, Kihei, HI 96753

Unfurnished 2 BR, 1 BA condo is ready to move into now. The unit is has been updated with new ceiling fans, paint, A/C, luxury vinyl laminate flooring, baseboards, doors, light fixtures, appliances and more.Water, sewer, basic cable, internet & standard trash removal is included in the rent as provided by the HOA. Tenant responsible for all other utilities including obtaining and

160 Keonekai Rd Unit 14-205, Kihei, HI 96753
/45
$1,636,000 Sold May 19, 2025

2715 Kauhale St, Kihei, HI 96753
- 4 Beds
- 4 Baths
- 2,509 Sq Ft
- Built 1987
Last Sold Summary
- 14% Below List Price
- $652/SF
- 135 Days On Market
Current Estimated Value $1,646,608

Last Listing Agent Miranda Watson Coldwell Banker Island Prop-Ku

2715 Kauhale St, Kihei, HI 96753

/27
Est $1,111,452 Not Listed For Sale

2757 S Kihei Rd Unit 803, Kihei, HI 96753
- 3 Beds
- 2 Baths
- 98,838 Sq Ft
- Built 2021
2757 S Kihei Rd Unit 803, Kihei, HI 96753

Last Sold Summary
- 24% Above List Price
- $9/SF
- 204 Days On Market
- Last Sold Price $899,000
- Apr 26, 2023
Last Listing Agent Geoffrey Cook Century 21 Island Homes

/50
$4,995,000 Open Sun 10AM - 4PM
- 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
/23
$2,250 Per Month
- 2 Beds
- 1 Bath
- 625 Sq Ft
- Updated 2-Bedroom Condo in Prime South Kihei Location in Keonekai Villages
160 Keonekai Rd, Kihei, HI 96753

Enjoy island living in this unfurnished 2-bedroom, 1-bathroom ground-floor condominium, ideally situated in a private-feeling area of the complex for added tranquility.This well-maintained unit has been thoughtfully updated with newer ceiling fans, fresh paint, a high-capacity air conditioner, new flooring, modern baseboard and trim, updated doors, light fixtures, blinds and some

160 Keonekai Rd, Kihei, 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 $1,089,476

Last Listing Agent Robbie Dein Maui Real Estate Advisors LLC

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

/28
Est $509,171 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
- 2% Below List Price
- $693/SF
- 77 Days On Market
- Last Sold Price $520,000
- Nov 15, 2024
Last Listing Agent Rhonda Faleafine Chris Bakeman Realty LLC

/48
$4,795,000
- 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
/16
$3,900 Per Month
- 2 Beds
- 2 Baths
- 733 Sq Ft
- Kihei Shores 2bd/2bth
2747 S Kihei Rd Unit H208, Kihei, HI 96753

Welcome to Kihei Shores!Experience the best of South Maui living in this stunning, top-floor residence at Kihei Shores. This Condo Offers offers a unique blend of modern luxury and island charm, located directly across the street from the golden sands of Kamaole Beach Park III.Condo is furnished, but can be unfurnished on request. Prime Location: As a top-level unit,

2747 S Kihei Rd Unit H208, 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 $3,421,816

Last Listing Agent Debbie Arakaki Compass

4000 Wailea Alanui Dr Unit 2003, 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
- $1/SF
- 3 Days On Market
- Last Sold Price $895,000
- Aug 25, 2023
Last Listing Agent Michael Mulski Pacific Image Properties

/50
$3,295,000 Open Thu 11AM - 2PM
- 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
/29
$2,875 Per Month
- 2 Beds
- 1 Bath
- South Kihei 2 Bedroom / 1 Bathroom Unfurnished downstairs unit - Peekaboo Ocean View
2709 Kauhale St, Kihei, HI 96753

This unfurnished 2 bedroom/ 1 bathroom downstairs unit is located in S. Kihei very close to Wailea. This unit has a flexible floor plan with options on how to set up the layout-it could be a 2 bedroom with a small living/dining room or it could be a 1 bedroom using the primary/second room as a big living room/office opening up to the lanai with other possible options. New dusk cherry luxury vinyl

2709 Kauhale St, 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 $471,243

Last Listing Agent Judy Boyd Equity Hawaii Real Estate LLC

2747 S Kihei Rd Unit J206, Kihei, HI 96753

/47
Est $2,657,291 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
- 4% Below List Price
- $738/SF
- 89 Days On Market
- Last Sold Price $2,760,000
- Jan 29, 2024
Last Listing Agent Eric West Real Broker

/50
$3,999,000
- 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
/16
$2,950 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
/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 $6,758,015

Last Listing Agent David Richardson Hawaii Life (W)

192 Halau Place, Kihei, HI 96753

/50
Est $534,308 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
- 5% Below List Price
- $741/SF
- 132 Days On Market
- Last Sold Price $560,000
- Dec 02, 2024
Last Listing Agent Aubrey Christopher Keller Williams Realty Maui-Ka

/40
$4,495,770
- 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
/76
$7,900 Per Month
- 3 Beds
- 3 Baths
- 2,350 Sq Ft
- Fully Furnished, 3 Bed/3 Bath, Wailea Kai Home with Saltwater Pool
29 Waikai St, Kihei, HI 96753

Welcome to 29 Waikai Place a private custom residence that features 3 bedrooms, 3 bathrooms, 2,350 sf single-level home with a garage. The home showcases an open layout with hardwood floors, furnishings, vaulted ceiling with a loft and boasts many unique qualities, including a salt water pool in a gated courtyard that has ultimate seclusion in a mature, tropical setting with exotic plants and

29 Waikai St, 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 $969,108

Last Listing Agent Matthew Iannaccio eXp Realty

2777 S Kihei Rd Unit 205, Kihei, HI 96753

/26
Est $522,891 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
- 17% Below List Price
- $1/SF
- 2 Days On Market
- Last Sold Price $630,000
- Nov 03, 2023
Last Listing Agent Kevin Spaise Keller Williams Realty Maui-Ki

/19
$2,495,000
- 4 Beds
- 3 Baths
- 3,195 Sq Ft
199 E Ikea Moku Place, Kihei, HI 96753

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 rhythm of the island sunrise coffee on the

Robbie Dein Maui Real Estate Advisors LLC

199 E Ikea Moku Place, Kihei, HI 96753
/65
$11,000 Per Month
- 3 Beds
- 3 Baths
- 1,742 Sq Ft
- Fully Furnished Luxury 3 Bedroom/3 Bathroom, La'i Loa in Wailea, New Build with Ocean Views
60 Kai Malu Dr, Kihei, HI 96753

Welcome to this stunning new build in the gated community of Wailea, Hawaii. Luxurious Villa offering fully furnished timeless color palette, three spacious bedrooms and three bathrooms, features a modern design with high-end finishes making this property truly remarkable.An open and airy floor plan of approximately 1742 square feet of ample space inside and an additional 465 square feet

60 Kai Malu Dr, 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 $1,679,578

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

71 Wailea Gateway Place Unit 7-203, 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
- $1/SF
- 26 Days On Market
- Last Sold Price $980,000
- Oct 09, 2023
Last Listing Agent Emalia Fisher Commercial Prop of Maui LLC

/48
$3,495,000 Open Sat 10AM - 3PM
- 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
/52
$8,500 Per Month
- 3 Beds
- 2.5 Baths
- 1,796 Sq Ft
- Front Row in KAI MALU, WAILEA, LUXURY 3bed/2.5bath Townhome with Unobstructed Panoramic Ocean Vie...
106 Kai La Place, Kihei, HI 96753

Peaceful and finely furnished luxury 3 bedroom, 2.5 bath townhome. The townhome, sitting on the front row of the complex, boasts amazing 180 degree ocean views showcasing the outer island of Lanai, Kaho'olawe and Molokini. The home is perched up the hill providing a grand lookout from the first floor, and even better views from the master bedroom on the second story, both levels enjoy private

106 Kai La Place, 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 $2,045,670

Last Listing Agent Dennis Rush Compass-W

126 Ponana St, Kihei, HI 96753

/13
Est $562,788 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
- 27% Below List Price
- $1/SF
- 11 Days On Market
- Last Sold Price $770,000
- Jan 17, 2024
Last Listing Agent Heidi Lynch Hawaii 5-0 Properties, Inc.

/50
$675,000
- 2 Beds
- 2 Baths
- 890 Sq Ft
2653 S Kihei Rd Unit 105, Kihei, HI 96753

At Maui Parkshore 105, days begin with the sound of the ocean and end with South Maui sunsets glowing across your lanai. This turnkey 2-bedroom, 2-bath condo offers a relaxed, close beach proximity lifestyle, where beach walks, warm breezes, and swaying palms are part of the everyday rhythm. Just across from Kamaole Beach Park III, you’re moments from soft sand, gentle waves, and one of Kihei’s

Clint Hansen Maui Luxury Real Estate LLC

2653 S Kihei Rd Unit 105, Kihei, HI 96753
/39
$8,000 Per Month
- 2 Beds
- 2 Baths
- **Modern Wailea Living**
36 Kai Malu Dr, Kihei, HI 96753

Experience luxury never lived in brand new stunning 2-bedroom, 2-bathroom condo nestled within a boutique building. Spanning an impressive 1375 sq. ft., this thoughtfully designed home seamlessly blends indoor and outdoor living, thanks to a grand sliding door that opens to a spacious 350sq. ft. lanai, complete with an outdoor wet bar and built-in BBQ – perfect for entertaining and enjoying the

36 Kai Malu Dr, Kihei, HI 96753
/24
$555,000 Sold May 14, 2025

160 Keonekai Rd Unit 18201, Kihei, HI 96753
- 2 Beds
- 2 Baths
- 750 Sq Ft
- Built 1992
Last Sold Summary
- 7% Below List Price
- $740/SF
- 3 Days On Market
Current Estimated Value $525,350

Last Listing Agent Mateo Manzari Coldwell Banker Island Prop-Ku

160 Keonekai Rd Unit 18201, Kihei, HI 96753

/49
Not Listed For Sale

2695 S Kihei Rd Unit 5-107, Kihei, HI 96753
- 1 Bed
- 2 Baths
- 818 Sq Ft
- Built 1983
2695 S Kihei Rd Unit 5-107, Kihei, HI 96753

Last Sold Summary
- $948/SF
- 187 Days On Market
- Last Sold Price $775,673
- Oct 04, 2024
Last Listing Agent Max Blair Coldwell Banker Island Prop(S)

Showing Results 81 - 120, Page 3 of 18

Hawaii Maui County Wailea

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