Makawao/Olinda/Haliimaile Pending Homes

Makawao, Olinda, and Hāliʻimaile together form the cultural and residential heart of Upcountry Maui. Defined by cooler temperatures, rolling terrain, and a strong sense of continuity, the area blends historic town character, forested slopes, and established neighborhoods. This part of Upcountry offers a grounded island environment that appeals to discerning buyers seeking long-term ownership rooted in land, tradition, and everyday livability rather than resort-oriented settings.

$1,185,000 Fee Simple

PENDING

3650 PIIKEA PL, Makawao

4 beds, 2.5 baths, 1,600 sq. ft., 8,516 sq. ft. lot

Listed by Compass-W

$1,150,000 Fee Simple

PENDING

284 ALALANI ST, Makawao

2 beds, 1 bath, 720 sq. ft., 0.5 acres lot

Listed by Shore To Shore Realty, Inc.

$1,100,000 Fee Simple

PENDING

742 KEKONA PL, Makawao

3 beds, 2 baths, 1,030 sq. ft., 7,031 sq. ft. lot

Listed by Coldwell Banker Island Prop-Ku

$955,000 Fee Simple

PENDING

1088 MAMALU PL, Makawao

3 beds, 2 baths, 1,006 sq. ft., 7,423 sq. ft. lot

Listed by Compass

$799,999 Fee Simple

PENDING

27 PAINA ST, Makawao

4 beds, 2.5 baths, 1,456 sq. ft., 0.27 acres lot

Listed by Real Broker

$799,000 Fee Simple

PENDING

22 PAKANI PL, Makawao

1 bed, 1 bath, 613 sq. ft., 10,881 sq. ft. lot

Listed by Compass-W

The residential market across Makawao, Olinda, and Haliimaile spans a broad range of property types and price points — from smaller homes near Makawao town to large forested estate properties in Olinda approaching 10 acres or more — making comparative market knowledge essential for buyers evaluating this area. Olinda in particular offers some of Upcountry's most private and estate-scale residential settings, with very limited inventory and strong demand from buyers seeking a genuine alternative to resort ownership. Mary Anne Fitch represents buyers and sellers across this Upcountry corridor with a career sales volume exceeding $1 billion. Contact Mary Anne directly to discuss current Makawao, Olinda, and Haliimaile home opportunities.