Wailea Kai Active Homes

Wailea Kai is one of the oldest and most established residential communities within the Wailea Resort, comprising 100 fee simple homesites on 34 acres with three gated entrances off South Kihei Road, Kilohana Drive, and Okolani Drive. Most homes were built between the mid and late 1980s and range from approximately 1,700 to over 4,000 square feet on lots of approximately 7,000 to 12,500 square feet, with cul-de-sac positioning providing additional privacy for many properties. The community is positioned directly across from Keawakapu Beach — one of South Maui's most consistently swimmable and least crowded beaches — and includes a private community park.

$2,500,000 Fee Simple

Wailea Kai

3142 WAIEA PL, Wailea

3 beds, 2.5 baths, 1,902 sq. ft., 9,348 sq. ft. lot

Listed by Coldwell Banker Island Prop-Ku

$2,499,000 Fee Simple

Wailea Kai

139 WAAULA WAY, Wailea

3 beds, 2.5 baths, 2,788 sq. ft., 10,616 sq. ft. lot

Listed by Coldwell Banker Island Prop-Ku

$2,325,000 Fee Simple

Wailea Kai

3236 PIKAI WAY, Wailea

4 beds, 3 baths, 1,894 sq. ft., 10,010 sq. ft. lot

Listed by Kokua Realty LLC

$2,295,000 Fee Simple

Wailea Kai

3150 WAIEA PL, Wailea

3 beds, 3 baths, 2,032 sq. ft., 0.28 acres lot

Listed by Hawaii Life (W)

$2,199,000 Fee Simple

Wailea Kai

30 WAIKAI ST, Wailea

3 beds, 2.5 baths, 2,129 sq. ft., 7,523 sq. ft. lot

Listed by Romvari Realty Ltd

$1,750,000 Fee Simple

Wailea Kai

53 WAIKAI ST, Wailea

4 beds, 2.5 baths, 2,400 sq. ft., 7,980 sq. ft. lot

Listed by Compass-W

Wailea Kai represents the most accessible price point among Wailea's gated single-family residential communities, a function of its 1980s construction vintage and generally flatter terrain that limits ocean views across most of the 100 homesites. For buyers prioritizing beach proximity over ocean views, the walking distance to Keawakapu Beach is arguably the strongest of any residential community in the resort. Renovation quality varies considerably across the neighborhood given the construction era, and buyers should evaluate individual home condition carefully. Mary Anne Fitch represents buyers and sellers within Wailea Kai with a career sales volume exceeding $1 billion. Contact Mary Anne directly for current availability.