WAILEA HOMES FOR SALE


Wailea is synonymous with refined island living, offering some of the most luxurious and architecturally stunning homes in all of Hawaii. Tucked along Maui’s southern coastline, Wailea’s residential communities are known for their privacy, panoramic ocean views, and meticulous attention to detail. From modern estates perched on the hillsides of Wailea Kialoa and Wailea Highlands to sprawling tropical compounds in gated neighborhoods like Maluhia at Wailea and Wailea Golf Vistas, homes for sale in Wailea offer the perfect balance of luxury, comfort, and island tranquility. These properties often feature spacious floor plans, open-air lanais, private pools, and lush landscaping designed to maximize indoor-outdoor living. Many homes are situated along world-class golf courses or offer sweeping views of the Pacific, with Molokini Crater and neighboring islands visible on the horizon. Wailea’s residential real estate is tailored for those seeking a full-time home, a seasonal retreat, or a private sanctuary surrounded by natural beauty and five-star amenities. With inventory limited and demand strong, working with a local expert like Roger Pleski gives you a competitive edge in navigating Wailea’s exclusive luxury home market.

Oceanfront Maui Real Estate

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New
3445 Lower Honoapiilani Rd 738, Kaanapali

$525,000

3445 Lower Honoapiilani Rd 738, Kaanapali

0 Beds 1 Bath 507 SqFt Residential MLS® # 411039

Keller Williams Realty Maui-L Cell: 808-250-5073

New
3543 Lower Honoapiilani Rd F403 24ab, Napili/Kahana/Honokowai

$15,000

3543 Lower Honoapiilani Rd F403 24ab, Napili/Kahana/Honokowai

2 Beds 2 Baths 1,127 SqFt Residential Income MLS® # 411035

Keller Williams Realty Maui-L Cell: 808-280-8986

New
3800 Wailea Alanui Dr F-302, Wailea/Makena

$7,495,000

3800 Wailea Alanui Dr F-302, Wailea/Makena

3 Beds 3.5 Baths 2,934 SqFt Residential MLS® # 411032

Compass-W

New Open House
210 Hauoli St, Maalaea

$6,995,000

210 Hauoli St, Maalaea

2 Beds 2 Baths 1,900 SqFt Residential
Sat, Oct 10th, 2026 @ 1pm - 4pm
MLS® # 411025

Hawaii Life (W) Cell: 808-283-2222

New
3600 Wailea Alanui Dr 2201, Wailea/Makena

$3,000,000

3600 Wailea Alanui Dr 2201, Wailea/Makena

2 Beds 2 Baths 1,347 SqFt Residential MLS® # 411022

Coldwell Banker Island Prop(S) Cell: 808-283-4189

New
300 Hauoli St B8, Maalaea

$825,000

300 Hauoli St B8, Maalaea

2 Beds 2 Baths 976 SqFt Residential MLS® # 411021

Hawaii Life (W) Cell: 808-870-8668

New
760 S Kihei Rd 310, Kihei

$1,650,000

760 S Kihei Rd 310, Kihei

3 Beds 2 Baths 1,126 SqFt Residential MLS® # 411020

Kumulani Vacations&Realty

New
100 Lio Pl K-4, Molokai

$505,000

100 Lio Pl K-4, Molokai

2 Beds 2 Baths 1,398 SqFt Residential MLS® # 411016

Hawaii Life (MO)

New
3600 Wailea Alanui Dr 2109, Wailea/Makena

$3,000,000

3600 Wailea Alanui Dr 2109, Wailea/Makena

2 Beds 2 Baths 1,536 SqFt Residential MLS® # 411018

Century 21 Island Homes

4809 Lower Honoapiilani Rd, Napili/Kahana/Honokowai

$19,750,000

4809 Lower Honoapiilani Rd, Napili/Kahana/Honokowai

7 Beds 8.5 Baths 8,412 SqFt Residential MLS® # 406991

Coldwell Banker Island Prop-KP Cell: 808-250-1583

100 Lio Pl B1, Molokai

$525,000

100 Lio Pl B1, Molokai

2 Beds 2 Baths 1,398 SqFt Residential MLS® # 410664

Molokai Island Properties

1 Bay Dr 2502, Kapalua

$5,975,000

1 Bay Dr 2502, Kapalua

3 Beds 3.5 Baths 2,904 SqFt Residential MLS® # 410884

Coldwell Banker Island Prop-KP Cell: 808-250-1583