Homes

South Maui

South Maui Pending Homes

South Maui luxury real estate extends along the island's southwestern shoreline from Maalaea Harbor through Kihei, Wailea, and Makena, encompassing some of Hawaii's most sought-after resort communities. Anchored by Wailea Resort — home to five championship golf courses, world-class hotels including the Four Seasons and Grand Wailea, and The Shops at Wailea — the region offers oceanfront estates, resort condominiums, gated communities, and premium homesites for sale. With consistent sunshine, calm beaches including Wailea Beach and Big Beach at Makena, and a highly developed resort infrastructure, South Maui attracts discerning buyers seeking refined coastal ownership with long-term value.

$35,000,000 Fee Simple

PENDING

3234 S KIHEI RD, Kihei

3 beds, 4.5 baths, 4,717 sq. ft., 0.96 acres lot

Listed by Hawaii Life (L)

$4,150,000 Fee Simple

PENDING

1656 HALAMA ST, Kihei

4 beds, 3 baths, 2,150 sq. ft., 0.46 acres lot

Listed by Compass-W

$3,500,000 Fee Simple

PENDING

Wailea Kai

39 HOAWAA WAY, Wailea

3 beds, 2 baths, 2,000 sq. ft., 8,699 sq. ft. lot

Listed by Maui Luxury Real Estate LLC

$3,060,000 Fee Simple

PENDING

3220 WAILEIA PL, Maui Meadows

3 beds, 2.5 baths, 2,053 sq. ft., 0.58 acres lot

Listed by Coldwell Banker Island Prop(S)

$2,180,000 Fee Simple

PENDING

614 KUPULAU PL, Maui Meadows

4 beds, 3 baths, 2,215 sq. ft., 0.56 acres lot

Listed by Engel & Volkers Maui

$2,100,000 Fee Simple

PENDING

870 KUPULAU DR, Maui Meadows

3 beds, 2.5 baths, 2,840 sq. ft., 0.54 acres lot

Listed by Compass-W

$1,275,000 Fee Simple

PENDING

129 OLUEA CIR, Kihei

4 beds, 2.5 baths, 2,298 sq. ft., 9,209 sq. ft. lot

Listed by Coldwell Banker Island Prop(S)

$1,250,000 Fee Simple

PENDING

Hale Piilani

530 KAIWAHINE ST, Kihei

7 beds, 4 baths, 2,478 sq. ft., 6,900 sq. ft. lot

Listed by HomeSmart Island Homes

$1,049,000 Fee Simple

PENDING

356 HOALIKE ST, Kihei

3 beds, 2 baths, 1,892 sq. ft., 7,109 sq. ft. lot

Listed by Keller Williams Realty Maui-Ka

$999,999 Fee Simple

PENDING

335 HOALIKE ST, Kihei

3 beds, 2 baths, 984 sq. ft., 7,279 sq. ft. lot

Listed by Maui & Co Real Estate LLC

$999,000 Fee Simple

PENDING

53 POLALE ST, Kihei

3 beds, 2 baths, 1,478 sq. ft., 4,134 sq. ft. lot

Listed by Century 21 Island Homes

$999,000 Fee Simple

PENDING

54 WAIAPO ST, Kihei

3 beds, 2 baths, 1,240 sq. ft., 5,793 sq. ft. lot

Listed by Coldwell Banker Island Prop(S)

$752,600 Fee Simple

PENDING

272 HOALIKE ST, Kihei

3 beds, 1.5 baths, 1,320 sq. ft., 7,614 sq. ft. lot

Listed by REALHome Services & Solutions

Luxury homes for sale in South Maui are concentrated in Wailea and Makena, where oceanfront estates, golf course residences, and gated coastal communities define the region's most prestigious addresses. From private beachfront homes in Makena to elevated ocean-view residences within the Wailea Resort, South Maui offers a curated selection of single-family homes in Hawaii's most refined resort setting. Mary Anne Fitch represents buyers and sellers of South Maui homes with a career sales volume exceeding $1 billion, specializing in oceanfront and resort-adjacent luxury residences. Inquiries are handled directly and discreetly.