Wailea, HI Homes

/50
$5,950,000

$1M PRICE DROP
- 5 Beds
- 4 Baths
- 4,718 Sq Ft
135 Kaimanu Place, Kihei, HI 96753

A rare South Maui estate — 2.118 acres in the exclusive gated community of Kaimanu Estates. This private retreat feels like living in Hana and Old Hawai‘i, surrounded by hundreds of native and fruiting trees including avocado, citrus, banana, lilikoi, guava and many more. With 4,718 sq. ft. in the main residence and a detached studio ohana, the property offers unmatched privacy and opportunity

Jennifer Edwards Coldwell Banker Island Prop(S)

135 Kaimanu Place, Kihei, HI 96753
/43
$2,495 Per Month
- 2 Beds
- 1 Bath
- 832 Sq Ft
- House for Rent
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 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 etc. New dusk cherry luxury vinyl planking recently installed

2709 Kauhale St, Kihei, HI 96753
/23
$650,000

Sold Aug 21, 2025

3950 Kalai Waa St Unit M102, Kihei, HI 96753
- 2 Beds
- 2 Baths
- 949 Sq Ft
- Built 1998
Last Sold Summary
- 13% Below List Price
- $685/SF
- 92 Days On Market
Current Estimated Value $854,588

Last Listing Agent Gary Mooers Coldwell Banker Island Prop(S)

3950 Kalai Waa St Unit M102, 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
- 187 Days On Market
Last Listing Agent Max Blair Coldwell Banker Island Prop(S)

/50
$13,495,000

$1M PRICE DROP
- 4 Beds
- 6 Baths
- 4,273 Sq Ft
4000 Wailea Alanui Dr Unit 1202/1204, Kihei, HI 96753

A 'WORK OF ART’. A 'LEGACY PROPERTY'. An ‘Equity Location’. A luxurious marriage of two Wailea Point oceanfront units at Maui's finest Condominium Project! When a lifelong collector with her heart in The Arts collaborates with a world-class interior designer, & engages Maui's most accomplished condominium contractor, the result is this ENVIRONMENT PAR-EXCELLENCE! Upon entering, it's like being on

Robbie Dein Maui Real Estate Advisors LLC

4000 Wailea Alanui Dr Unit 1202/1204, Kihei, HI 96753
/28
$2,500 Per Month
- 2 Beds
- 1 Bath
- 625 Sq Ft
- Condo for Rent
160 Keonekai Rd, Kihei, HI 96753

Welcome to Keonekai Villages, just a short distance away from beaches, dinning, shopping and schools you will find yourself conveniently located to everything South Kihei has to offer.This 2 bedroom, 1 bathroom, 2nd floor, approximately 625 sq. ft. unfurnished condo will be ready to call home. Luxury vinyl plank flooring throughout kitchen, living area and bedrooms. New Refrigerator. For

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 $1,060,946

Last Listing Agent Robbie Dein Maui Real Estate Advisors LLC

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

/31
Not Listed For Sale

160 Keonekai Rd Unit 16-202, Kihei, HI 96753
- 2 Beds
- 2 Baths
- 750 Sq Ft
- Built 1992
160 Keonekai Rd Unit 16-202, Kihei, HI 96753

Last Sold Summary
- 3 Days On Market
Last Listing Agent Mateo Manzari Coldwell Banker Island Prop-Ku

/50
$13,900,000
- 3 Beds
- 3 Baths
- 3,850 Sq Ft
4000 Wailea Alanui Dr Unit 1602, Kihei, HI 96753

FABULOUS world class Wailea Point “double” unit with a MOST DYNAMIC ocean & beach front location. Perhaps the finest condominium residence in Hawaii, no expense was spared to set this exclusive Maui home apart. Unsurpassed world class views, from iconic Polo Beach and the Makena coastline, to the vast Pacific and offshore islands, and north to the Kihei & Maalaea coastlines. Just steps to the

Dave Wagner Wailea Point Realty, Inc.

4000 Wailea Alanui Dr Unit 1602, Kihei, HI 96753
/40
$695,000

Sold Jul 24, 2026

69 Piilaniwahine Loop Unit 1902, Kihei, HI 96753
- 3 Beds
- 3 Baths
- 1,180 Sq Ft
- Built 2017
Last Sold Summary
- 10% Below List Price
- $589/SF
- 203 Days On Market
Current Estimated Value $715,532

Last Listing Agent Lee Wheeler Keller Williams Realty Maui-Ki

69 Piilaniwahine Loop Unit 1902, Kihei, HI 96753

/32
Est $557,273

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

/50
$4,650,000

$240K PRICE DROP
- 3 Beds
- 4 Baths
- 2,619 Sq Ft
21 Kiloa St Unit 4, Kihei, HI 96753

E Komo Mai and welcome to Ho'olei 21-4, an elegant 3 bed, 3.5 bath townhome located in the heart of Wailea, Maui. This Hotel Zoned property boasts wonderful ocean views and is offered tastefully furnished, totally turnkey, and is active and successful in the Grand Wailea's exclusive vacation rental program. The Plumeria floor plan enjoys the widest lanai and forward most position of the building,

Lucas Woodford Hawaii Life (W)

21 Kiloa St Unit 4, 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 $3,308,389

Last Listing Agent Debbie Arakaki Compass

4000 Wailea Alanui Dr Unit 2003, Kihei, HI 96753

/49
Est $3,959,654

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
Last Listing Agent Peter Slate Coldwell Banker Island Prop(S)

/49
$1,595,000

$355K PRICE DROP
- 4 Beds
- 3 Baths
- 2,203 Sq Ft
301 Ohina Place, Kihei, HI 96753

Gorgeous home with a legal attached ohana located on a quiet cul-de-sac just up the hill from Kamaole Beach Park III and Keawakapu Beach. This distinctive property, constructed with beautiful cedar siding on a solid slab foundation, features a 4-bedroom, 2-bath main home on the upper level with open beam vaulted ceilings, dual system air conditioning, and a fully remodeled kitchen. The home also

Travis Speck Redfin Corporation

301 Ohina Place, 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 $456,913

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
Last Listing Agent Alan Craig Coldwell Banker Island Prop-Ku

/46
$5,395,000

$705K PRICE DROP
- 2 Beds
- 2 Baths
- 1,978 Sq Ft
3800 Wailea Alanui Dr Unit 511, Kihei, HI 96753

Welcome to this stunning top-floor oceanfront residence in the exclusive Penthouse building at Wailea Beach Villas. This tranquil 2-bedroom, 2-bath villa offers over 2,000 square feet of thoughtfully designed indoor and outdoor living space, seamlessly blending contemporary elegance with relaxed island sophistication. Perched approximately 100 feet above the Pacific Ocean, the villa showcases

Myriam Haynal Coldwell Banker Island Prop-Ku

3800 Wailea Alanui Dr Unit 511, 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 $6,560,469

Last Listing Agent David Richardson Hawaii Life (W)

192 Halau Place, Kihei, HI 96753

/45
Est $566,012

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
Last Listing Agent Dennis Rush Compass-W

/37
$819,000

$30K PRICE DROP
- 1 Bed
- 2 Baths
- 818 Sq Ft
2695 S Kihei Rd Unit 10-213, Kihei, HI 96753

Welcome to your Maui getaway at Kamaole Sands, Building 10! This 1 bedroom, 2 bathroom condo has been completely upgraded and designed with comfort and style in mind. One of the best features is the large lanai with sweeping ocean views — it truly feels like an extra room where you can relax, dine, or just soak in the sunsets. Inside, you’ll find tile flooring throughout and a custom built-in

Alex Abreu Hawaii Life (W)

2695 S Kihei Rd Unit 10-213, 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 $895,977

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
Last Listing Agent Geoffrey Cook Century 21 Island Homes

/50
$2,595,000

$100K PRICE DROP
- 4 Beds
- 4 Baths
- 2,129 Sq Ft
100 Poailani Place Unit 29, Wailea-Makena, HI 96753

Also listed as Residential MLS# 409490. In the best location in Kanani Wailea, adjacent to expansive open space and unobstructed ocean views, this exceptional single-level residence offers the community’s most desirable floor plan. Located in an exclusive gated enclave of just 38 detached residential condominiums, this beautifully appointed 4-bedroom, 4-bath home blends luxury, privacy, and

Don McEntire McEntire Realty

100 Poailani Place Unit 29, Wailea-Makena, 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 $1,652,138

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

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

/50
Est $3,898,290

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
Last Listing Agent Dale Richardson Hawaii Life (W)

/48
$2,200,000

$350K PRICE DROP
- 4 Beds
- 3 Baths
- 2,215 Sq Ft
614 Kupulau Dr, Kihei, HI 96753

Up to 3 units total. 3 Bed 2 Bath Main Dwelling + Attached Studio Ohana + 1 Bed 1 Bath Unattached Cottage Ohana with lanais on both buildings. Maui Meadows is renowned for its awe-inspiring ocean views. Prominently situated with a single level on the hillside, you'll discover within this contemporary elegant home, a spacious living-room kitchen area that seamlessly extends to the highlight of the

Lucas Peterson Bello Realty Inc

614 Kupulau Dr, Kihei, HI 96753
/50
$3,500,000

Sold Jul 16, 2026

60 Kai Malu Dr Unit 202 (11D), Kihei, HI 96753
- 3 Beds
- 3 Baths
- 1,742 Sq Ft
- Built 2023
Last Sold Summary
- 10% Below List Price
- $2,009/SF
- 225 Days On Market
Last Listing Agent Dale Richardson Hawaii Life (W)

60 Kai Malu Dr Unit 202 (11D), Kihei, HI 96753

/50
Est $1,198,944

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
Last Listing Agent Geoffrey Cook Century 21 Island Homes

/49
$4,795,000
- 3 Beds
- 4 Baths
- 2,386 Sq Ft
3100 Wailea Alanui Dr Unit 17, Kihei, HI 96753

Where do timeless design, ultimate privacy, and panoramic ocean vistas all converge in Wailea? Welcome to Papali #17. Perfectly positioned in the community’s premier location, this exquisite residence is being offered for the first time since the original developer release. This single-level three bedroom and three-and-a-half baths provides the comfort and presence of a private home with the

Dano Sayles Coldwell Banker Island Prop(S)

3100 Wailea Alanui Dr Unit 17, 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 $1,946,816

Last Listing Agent Dennis Rush Compass-W

126 Ponana St, 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
Last Listing Agent Sara Fox Keller Williams Realty Maui-Ki

/43
$3,300,000
- 2 Beds
- 3 Baths
- 1,584 Sq Ft
4000 Wailea Alanui Dr Unit 2101, Kihei, HI 96753

Wailea Point 2101 is a rare, single-level residence featuring 2 bedrooms and 3 bathrooms with the convenience of no-stair entry. Enjoy breathtaking ocean and garden views, complemented by the stunning “bonus” views of Haleakala and the West Maui mountains. The open-concept kitchen is perhaps the most popular remodel scope of work in Wailea Point, and it’s already done in this lovely home,

Dave Wagner Wailea Point Realty, Inc.

4000 Wailea Alanui Dr Unit 2101, 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 $2,564,094

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

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

/50
Est $3,262,194

Not Listed For Sale

3187 Nahenahe Place, Kihei, HI 96753
- 3 Beds
- 4 Baths
- 2,780 Sq Ft
- Built 2007
3187 Nahenahe Place, Kihei, HI 96753

Last Sold Summary
- 171 Days On Market
Last Listing Agent Nancy Nevius Coldwell Banker Island Prop(S)

/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
/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 $3,104,843

Last Listing Agent Todd Hudson Keller Williams Realty Maui-Ki

904 Kupulau Dr, Kihei, HI 96753

/34
Est $2,266,345

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
Last Listing Agent Mark Waite Compass-W

/50
$4,995,000

Pending
- 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 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

Showing Results 81 - 120, Page 3 of 18

Hawaii Maui County

How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Wailea, HI Homes

Real Estate & Homes