Homes

Upcountry

Makawao/Olinda/Haliimaile 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.

Active (30)

Pending (6)

$4,750,000 Fee Simple

2450 PIIHOLO RD, Makawao

3 beds, 3.5 baths, 3,229 sq. ft., 10.15 acres lot

Listed by Coldwell Banker Island Prop(P)

$4,400,000 Fee Simple

2350 BALDWIN AVE #B, Makawao

2 beds, 3 baths, 992 sq. ft., 1.44 acres lot

Listed by Hawaii Life (W)

$3,400,000 Fee Simple

61 KEE RD, Makawao

4 beds, 3 baths, 2,914 sq. ft., 9.62 acres lot

Listed by Equity One Real Estate Inc (M)

$3,200,000 Fee Simple

NEW

170 KEE RD, Makawao

3 beds, 2 baths, 1,183 sq. ft., 4.3 acres lot

Listed by REMAX Hawaii Maui

$2,649,000 Fee Simple

1740 PIIHOLO RD, Makawao

5 beds, 3.5 baths, 3,712 sq. ft., 4.39 acres lot

Listed by Coldwell Banker Island Prop(S)

$2,641,000 Fee Simple

143 LEIOHU CIR, Makawao

3 beds, 2.5 baths, 2,326 sq. ft., 0.47 acres lot

Listed by Keller Williams Realty Maui-Ki

$2,350,000 Fee Simple

15 OLINDA RD, Makawao

5 beds, 4 baths, 1,191 sq. ft., 0.54 acres lot

Listed by eXp Realty

$1,825,000 Fee Simple

179 MAIAKU ST #LOT 165, Makawao

4 beds, 3 baths, 1,456 sq. ft., 7,503 sq. ft. lot

Listed by Island Sotheby's International Realty(L)

$1,725,000 Fee Simple

139 MAIAKU ST #LOT 168, Makawao

4 beds, 2.5 baths, 2,280 sq. ft., 7,552 sq. ft. lot

Listed by Island Sotheby's International Realty(M)

$1,700,000 Fee Simple

NEW

85 ULANA ST, Makawao

5 beds, 3 baths, 1,696 sq. ft., 0.54 acres lot

Listed by Commercial Prop of Maui LLC

$1,650,000 Fee Simple

156 ALALUANA RD, Makawao

2 beds, 2 baths, 1,831 sq. ft., 2.93 acres lot

Listed by Coldwell Banker Island Prop(P)

$1,549,000 Fee Simple

640 MAKAWAO AVE, Makawao

4 beds, 2 baths, 1,602 sq. ft., 2.48 acres lot

Listed by Keller Williams Realty Maui-Ka

$1,525,000 Fee Simple

189 HOKUPA ST #LOT 36, Makawao

4 beds, 2.5 baths, 1,715 sq. ft., 7,573 sq. ft. lot

Listed by Island Sotheby's International Realty(L)

$1,500,000 Fee Simple

1160 EHU RD, Makawao

3 beds, 2 baths, 1,536 sq. ft., 2.5 acres lot

Listed by Island Sotheby's International Realty(M)

$1,475,000 Fee Simple

1102 MAILUNA PL, Makawao

3 beds, 3 baths, 2,323 sq. ft., 7,610 sq. ft. lot

Listed by Equity One Real Estate Inc (P)

$1,399,000 Fee Simple

2400 PIIHOLO RD, Makawao

3 beds, 2 baths, 2,760 sq. ft., 2 acres lot

Listed by Coldwell Banker Island Prop(Ka)

$1,350,000 Fee Simple

35 PUKIKI PL #A, Makawao

6 beds, 4 baths, 2,304 sq. ft., 0.44 acres lot

Listed by Coldwell Banker Island Prop(S)

$1,295,000 Fee Simple

305 IINI WAY, Makawao

4 beds, 3.5 baths, 2,108 sq. ft., 5,401 sq. ft. lot

Listed by Equity One Real Estate Inc (M)

$1,239,000 Fee Simple

185 HOLOLANI ST, Makawao

3 beds, 2.5 baths, 1,592 sq. ft., 10,698 sq. ft. lot

Listed by Coldwell Banker Island Prop(S)

$1,200,000 Fee Simple

1199 FREITAS PL PL, Makawao

3 beds, 2 baths, 1,635 sq. ft., 0.39 acres lot

Listed by Chris Bakeman Realty LLC

$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

$1,169,000 Fee Simple

40 LEIE ST, Makawao

4 beds, 2 baths, 1,695 sq. ft., 8,999 sq. ft. lot

Listed by Keller Williams Realty Maui-Ka

$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.

$1,125,000 Fee Simple

3586 KALUA PL, Makawao

3 beds, 2 baths, 1,652 sq. ft., 5,915 sq. ft. lot

Listed by Nathalie Mullinix Rlty Universal Inc

$1,125,000 Fee Simple

16 MAKANI RD, Makawao

4 beds, 3 baths, 1,404 sq. ft., 6,000 sq. ft. lot

Listed by Equity One Real Estate Inc (M)

$1,100,000 Fee Simple

29 MIKIOLA ST, Makawao

2 beds, 1 bath, 0.5 acres lot

Listed by ZT Hawaii LLC

$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

$1,095,000 Fee Simple

30 PAHAA PL, Makawao

4 beds, 3 baths, 1,020 sq. ft., 0.27 acres lot

Listed by Keller Williams Realty Maui-Ka

$999,000 Fee Simple

37 PUKIKI PL #B, Makawao

2 beds, 1 bath, 1,001 sq. ft., 1.87 acres lot

Listed by Coldwell Banker Island Prop(S)

$989,000 Fee Simple

2840 KOEA PL, Makawao

3 beds, 1.5 baths, 1,152 sq. ft., 0.28 acres lot

Listed by Corcoran Pacific Properties

$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

$750,000 Fee Simple

918 HIILANI ST, Makawao

3 beds, 2 baths, 758 sq. ft., 7,349 sq. ft. lot

Listed by Realty 1st Inc

$750,000 Fee Simple

3566 KALUA PL, Makawao

4 beds, 2 baths, 1,050 sq. ft., 4,704 sq. ft. lot

Listed by Tri-Isle Rlty & Dev Co Inc

1018 ULELE ST #UNIT B, MAKAWAO, HI 96768

$744,000 Fee Simple

NEW

1018 ULELE ST #UNIT B, Makawao

2 beds, 1 bath, 600 sq. ft., 10,742 sq. ft. lot

Listed by Keller Williams Realty Maui-Ka

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.