Roofing contractor in Makawao, HI

Makawao is a historic paniolo town on the slopes of Haleakala in Upcountry Maui, sitting at elevations where the climate is noticeably cooler and wetter than the coast. The housing stock ranges from old plantation-style cottages in town to half-acre lots in neighborhoods like Maui Uplands and large ranch estates in the Olinda area above town. Because Makawao sits on the windward side of Upcountry, it receives more rainfall than neighboring Kula, and roofs here face more frequent wet cycles that promote moss growth and accelerate shingle aging. Steep lot grades and long driveways on larger properties add access complexity that coastal roofing jobs rarely present.

Call (808) 463-0261
Service Location

Makawao, HI

HI Service Area

No extra travel fees for this area

Communities we serve

Makawao Pukalani Haliimaile Olinda
  • Nearly 20 Years Local
  • 100% Local, Family-Owned
  • Free Estimates
  • Maui Roofing Specialist
Wood shake roofing being installed on a large ranch-style home in the Olinda area above Makawao, showing the layered shake pattern against a green upcountry landscape.

Makawao, HI

Roofing Contractor

Upcountry Conditions, Upcountry Expertise: Makawao Roofing

Makawao's position on the windward side of Upcountry Maui means roofs here see more rainfall than in Kula or the coastal towns below. That moisture supports moss and algae growth on shingles, which traps additional water and accelerates granule loss. We account for this when selecting underlayment and recommend ridge ventilation details that help roofs dry out between rain events.

Property access in Makawao is a real logistical factor. Homes in the Olinda area and on larger lots above town often have long, steep driveways that limit how materials can be staged and moved. We plan access routes and material delivery before the job starts, so the work proceeds without damage to driveways or landscaping.

The mix of old plantation cottages in Makawao town and large ranch-style estates above it means no two roofing jobs here are the same. We have worked on both ends of that spectrum across Maui for close to two decades. Whether the job is a modest shingle replacement on a town cottage or a full wood shake install on an Olinda estate, we give you a free estimate and price the work to be affordable.

At a glance

  • Locally owned and operated
  • Free written estimates with no obligation
  • Premium options most contractors don't carry — we explain the differences honestly
  • Responsive scheduling and clear communication from estimate to completion
Call (808) 463-0261

Every service, available in Makawao, HI

Asphalt shingles are the most practical replacement material for Makawao's plantation-style homes, where the roof pitch and deck construction suit standard shingle installation well. Wood shakes are a natural fit for the ranch estates and larger properties in the Olinda area, where the aesthetic matches the rural character and the cooler, wetter climate is actually more forgiving to wood roofing than the dry coastal zones. Corrugated metal is gaining traction on newer Upcountry builds because it sheds Makawao's frequent rain events quickly and does not support the moss growth that shortens shingle life in this wetter microclimate.

What Makawao, HI customers say.

4.9
34 Google reviews

Worked with us?

Leave a Review

Our roof needed repair after a storm and Jason responded quickly and professionally. He did the repairs within a few days and did an excellent job. We greatly appreciate his work.

Athena Anderson Google review · March 2026

Jason, was very quick to respond and willing to work with you on scheduling. Him and his crew did an amazing job well recommend. Thank You, J’s Quality Roofing

Shay Google review · June 2026

Jason and his crew were great! They were mindful of any rubbish and checked around the house before they left. There was an issue, but Jason took care of it right away. When unexpected things came up, he notified me first before moving forward with the job. Overall, I am satisfied with my roof.

Tiffany Kesaji Google review · February 2026

Jason was courteous and professional. He communicated well throughout the entire process and delivered when it came to doing a quality job. I would recommend to family and friends that are looking to do a repair or and entire roof.

Chuck Dando Google review · May 2025

The moment we first contacted Jason for a quote for re-roofing our house, we immediately got a response from him. He was very prompt, and answered all of our questions. After gathering a few estimates for this project, Jason stood out of the rest of the roofers we inquired from. His price was very fair and the most reasonble. He and his team did a nice job on our roof! He went above and beyond, definitely met our expectations. He is just a call away and he’ll take quick action. Definitely would recommend Jason and his team for all roofing needs.—-James Marquez

Sandra Marquez Google review · December 2025

Recent projects

See all projects
Black rolled roofing membrane with white backing being installed on substrate Waterproofing service
Wood shake shingles with natural grain texture and proper installation overlap Roofing contractor
Architectural asphalt shingles with gray, brown, and blue-green coloring installed with proper overlap Roofing contractor

Serving Makawao, HI

Free on-site estimate. No commitment required.

Our crew knows Makawao, HI. We will show up on time, assess the job honestly, and give you a clear written number before asking you to decide anything.

Call (808) 463-0261

Roofing Contractor FAQ for Makawao, HI

Common questions from Makawao, HI customers about our services, process, and coverage.

Makawao sits on the windward side of Upcountry Maui and receives significantly more rainfall than South Maui communities like Kihei. That moisture, combined with cooler temperatures and shade from surrounding vegetation, creates ideal conditions for moss and algae growth on shingles. Proper ventilation and the right shingle product can slow that growth considerably.

Wood shakes work well on Olinda-area ranch properties because the cooler, wetter Upcountry climate is more forgiving to wood roofing than the dry, UV-intense coastal zones. The aesthetic also fits the rural character of larger estate properties. We inspect the deck and framing before installation to confirm the structure is ready for the weight and profile of wood shakes.

Yes, we plan material staging and access routes for properties with challenging driveways before the job starts. Homes in the Olinda area and on larger Upcountry lots often require different logistics than a standard coastal job, and we account for that in the estimate so there are no surprises on the day work begins.

Makawao's frequent rain cycles put more wet-dry stress on roofing materials than drier parts of Maui. Shingles in this zone tend to age faster than the same product installed in Kihei or Wailea. Choosing a shingle with a higher moisture resistance rating and ensuring proper attic ventilation can extend the replacement interval meaningfully.

Still have questions?

Call us directly. Real answers, no scripts.

Call (808) 463-0261

Proudly Based in Kahului, HI

Stop by, call, or book online — we're always nearby when you need us.

Hours

  • Monday 7:30 AM - 5:00 PM
  • Tuesday 7:30 AM - 5:00 PM
  • Wednesday 7:30 AM - 5:00 PM
  • Thursday 7:30 AM - 5:00 PM
  • Friday 7:30 AM - 5:00 PM
  • Saturday 7:30 AM - 5:00 PM
  • Sunday Closed

Get a Free Estimate