Orland Roofing Contractor | Serving Orland From Winter Harbor
Same-Day Appointments Available · 24/7 Emergency Service
GAF & CertainTeed certified. 22 years in business. Protecting Orland roofs from Winter Harbor.
Call (877) 349-1553Same-day estimates · GAF certified crews ready
If your Orland home needs a new roof or a repair, Winter Harbor Roofing & Maintenance is the contractor to call. We're based in Winter Harbor and our crews are in Orland every week, inspecting roofs, replacing shingles, and handling storm damage claims.
Our Services in Orland
What Orland Customers Say
"Their crew showed up at 7 AM, tore off the old roof, replaced eight sheets of plywood, and had new shingles down before dinner. Jobsite was cleaner when they left than when they arrived."
"Hail punched through half our shingles last spring. Winter Harbor Roofing & Maintenance handled the entire insurance claim — met the adjuster, filed the supplement, and we paid nothing out of pocket besides the deductible."
Why Orland Residents Choose Winter Harbor Roofing & Maintenance
Free Inspections & Honest Estimates
We don't charge for inspections and we don't pad estimates. If your Orland roof needs a repair, we'll tell you. If it needs a replacement, we'll explain exactly why. No high-pressure sales, no scare tactics.
Storm Damage Specialists
Hail, wind, and monsoon damage are common in ME. Our team includes HAAG Certified inspectors who document damage the way adjusters expect it. We handle the entire insurance claim process so you don't have to.
Manufacturer-Certified Installation
We hold certifications from GAF, Owens Corning, and CertainTeed. That means the manufacturers have trained and vetted our crews and will back our installations with their strongest warranties. Your Orland roof gets factory-level quality control.
22+ Years of Experience
We've been installing and repairing roofs for over 22 years. That experience shows in how we handle complex roof lines, unexpected deck damage, and insurance claim disputes. We've seen everything and know how to handle it.
About Our Orland Roofing Services
Our Orland customers get the same crew quality, warranty coverage, and pricing as our Winter Harbor clients. No travel surcharges, no subcontracted labor, no shortcuts. We use our own trained crews on every job.
The first step is always a free inspection. Call (877) 349-1553 and we'll have a certified inspector at your Orland property within a couple of days. Storm damage? We prioritize those calls and can usually get out same-day.
Orland homeowners get priority scheduling from our Winter Harbor office. We've been working in Orland for years and our crews know every neighborhood.