Honest Quotes. Quality Craftsmanship. Fully Certified & Insured.
Ontario's Trusted Roofer Since 2008.
Honest Quotes. Quality Craftsmanship. Fully Certified & Insured.
Ontario's Trusted Roofer Since 2008.
Emergency Roof Repairs
Fast response for leaks and wind damage.
17+ Years Roofing
Locally
Serving Southern Ontario, Muskoka & Parry Sound since 2008.
Certified by Leading Brands
Partnered with top-tier manufacturers to offer premium coverage on all roofing systems.
Fully Insured Local Roofing Contractor
Full liability coverage for your peace of mind.
- Mark Ollerenshaw
Owner of Ollie's Roofing
We Build Relationships.
Hi, I’m Mark.
For over 17 years, my team and I have treated every roof in Ontario like it’s our own mother’s home.
We don't use high-pressure sales tactics—just honest inspections and clear quotes.
Whether it’s a simple leak repair or a full replacement, you get Manufacturer Certified craftsmanship and a crew that cleans up every nail before we leave.
Experience the Ollie's difference and see why we have hundreds of 5 star reviews!
WHY CHOOSE OLLIE'S?
Your Neighbours in Southern Ontario.
We aren't a franchise. We are a local, family-run team that has weathered the same ice storms you have. While other roofers chase storms and leave town, we stay right here to stand behind our work.
From the first inspection to the final nail sweep, you deal directly with us—no middlemen, no hidden fees.
OUR SERVICES
Complete Roof Protection For Your Home And Business,
Serving All Of Southern Ontario, Muskoka & Parry Sound
Roof
Replacement
Asphalt Shingle & Metal
Manufacturer-certified installations with industry-leading products. We provide a full tear-off, inspect your decking, and ensure a flawless install. We guarantee a clean site—we sweep for every last nail!
Roof Repairs &
Emergencies
Leak Detection & Ice Dams
Fast response for wind damage, missing shingles, and winter ice dams. Our experts find and fix the "invisible" leaks that others miss, protecting your home from further water damage.
Soffit, Fascia &
Eavestroughs
Curb Appeal & Efficiency
Enhance your home’s aesthetics with precision-installed soffit and fascia, paired with seamless eavestroughs for a clean, maintenance-free look you'll love forever.
Commercial
Roofing
Flat & Industrial Roof Experts
We specialize in TPO, EPDM, and Tar & Gravel roofs for plazas, warehouses, and multi-unit buildings. We offer repairs, replacements, and maintenance plans to keep you protected.
Trusted Roofing & Exterior Solutions Across the Halton Region & Beyond
At Ollie’s Roofing, we don’t just install shingles; we engineer protection for the unique climate of Southern Ontario. From the high-wind pressures along the Niagara Escarpment in Milton to the heavy snow loads and freeze-thaw cycles common in Muskoka and Parry Sound, your roof faces extreme conditions. Since 2008, our mission has been to provide homeowners in Burlington, Oakville, and Halton Hills with high-performance roofing systems that exceed industry standards.
We specialize in Asphalt Shingle Replacement, utilizing manufacturer-certified techniques that qualify you for extended, gold-standard warranties. But a roof is only as good as its ventilation. That is why we focus heavily on the "Roofline Trifecta": Soffit, Fascia, and Seamless Eavestroughs. Proper attic ventilation prevents ice damming—a major concern for older homes in the Halton Region—while precision-installed gutters protect your home’s foundation from water intrusion.
How much does a roof replacement cost in Milton?
Costs vary based on square footage and material choice, but most homeowners in the Halton Region can expect an investment between $5,000 and $15,000 for a standard residential roof. We provide detailed, transparent estimates to ensure no hidden fees.
What is the best roofing material for Ontario weather?
We highly recommend high-definition architectural asphalt shingles. They offer the best balance of wind resistance (up to 130 mph) and durability against Southern Ontario’s intense UV summer rays and heavy winter ice.
Do you offer emergency roof repairs in Halton?
Yes. We provide fast-response leak detection and emergency tarping services for wind and storm damage in Milton, Burlington, and surrounding areas to prevent further interior water damage.
How do I know if I need a roof repair or a full replacement?
If your roof is over 15–20 years old or has widespread shingle curling and granule loss, a replacement is often more cost-effective. Small leaks or missing shingles from a single storm can usually be addressed with a targeted repair.
Do you install seamless eavestroughs in Muskoka and Parry Sound?
Yes, we provide full gutter and trim services, including seamless eavestroughs, soffit, and fascia, across Southern Ontario, including the Muskoka and Parry Sound regions.
Are you fully insured for roofing in the Halton Region?
Absolutely. Ollie’s Roofing carries full liability insurance and WSIB coverage for all projects in Milton, Burlington, Oakville, and surrounding areas to protect our clients and our crew.
Our Experience
Commercial Flat Roof Specialists
Protecting Ontario businesses from costly overhead water damage.
We are experts in TPO, EPDM, and Tar & Gravel flat roofing systems. From urgent leak repairs on warehouses to full roof replacements for retail plazas, our team works efficiently to minimize disruption to your operations and tenants.
Don't wait for a ceiling stain to call us.
Ask about our proactive Annual Maintenance Packages to extend the life of your roof.
Plazas & Retail Strips
Warehouses & Industrial
Condo & Townhouse Complexes
Multi-Unit Residential
Other Commercial Properties
Stop The Leak Before It Gets Worse...
Portfolio
Our Recent Work
MEET THE CREW
The People Protecting Your Home.
Mark
Ollerenshaw
Founder & CEO
Mike
Rego
Sr. Roofing Consultant / Estimator
Pam
Kerr
Project Coordinator
Mark
Almeida
Roofing Estimator
Sandy
Davidson
Roof Service Coordinator
Simon
Ovens
Roof Repair & Service Manager
Norm
Johnston
Roofing Estimator
Ben
Ronnenberg
Marketing Director
roof leak & roof repair services in ontario, CANADA
Commercial & Residential Roofing Solutions
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Zero-spam promise.
From repairs to replacements, our expert team provides durable and trustworthy roofing services to protect your home. Contact us today!
Call Ollie's for ROOFING HELP 24/7
Our Services
Residential Roofing
Commercial Roofing
Roofing Repairs
Asphalt Shingle Roofing
Metal Roofing
Latest Blogs
The Ultimate Ontario Winter Home Roof Guide | Ollie's Roofing
Expert winter roof protection guide for Ontario, GTA & Muskoka. 23 years of authority on ice damming, snow loads, and attic insulation. Get a Free Estimate on any roof repair or replacement project! ...more
Winter Roofing
January 09, 2026•7 min read
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Head Office
32 Steeles Ave E #11, Milton, ON L9T 5A1, Canada