More Than Just a Roofer:
An 18-Year Legacy in Ontario
In an industry plagued by fly-by-night contractors and fluctuating standards, Ollie’s Roofing Ltd. has stood as a pillar of consistency since 2008. We aren't just building roofs; we are building a legacy of trust, one home at a time, from the suburban streets of Milton to the lakeside cottages of Muskoka.
The Ollie's Story: Built on a Foundation of Integrity
Mark Ollerenshaw founded Ollie’s Roofing Ltd. with a simple but powerful vision: to bring a higher level of professionalism and technical expertise to the residential & commercial roofing markets in Ontario.
2008: The Beginning. Starting with a single truck and a commitment to doing things the right way, Mark began building a reputation in the Halton region for honest work and transparent pricing.
The Growth Years. Fueled almost entirely by word-of-mouth referrals, the company grew. We didn't expand by cutting corners; we expanded by refusing to compromise on quality.
Expanding Horizons. Recognizing the unique challenges of cottage country, Ollie’s Roofing brought its expertise north to Muskoka, becoming a trusted name for high-stakes custom metal and steep-slope projects.
Today: The 18-Year Standard. Nearly two decades later, our core values remain unchanged. We are large enough to handle any project but remain locally owned and personally invested in every job we undertake.
The "Ollie's Difference": Our Code of Ethics
Why do thousands of Ontario homeowners trust us with their most valuable asset? Because we operate by a strict code that puts the homeowner first.
The "No-Pressure" Consultation
We don't employ aggressive salespeople. Our estimates are conducted by experienced roofing professionals whose goal is to educate, not intimidate. We provide detailed, itemized quotes—no hidden fees, no surprise upcharges.
The Owner's Eye
Mark Ollerenshaw is not an absentee owner. He maintains an active role in the company, ensuring that the standards he set in 2008 are met on job sites today. This culture of accountability permeates our entire team.
Respect for Your Home
A roof replacement is a major construction project, but it shouldn't turn your life upside down. Our crews are trained to treat your property with the utmost respect. From protecting your landscaping with tarps to our meticulous daily magnetic nail-sweeps, we aim to leave your property cleaner than we found it.
Meet the Founder: Mark Ollerenshaw
- Mark Ollerenshaw
Owner of Ollie's Roofing
Mark is a master tradesman who believes that true expertise comes from hands-on experience. He didn't learn roofing from a textbook; he learned it on the roof decks of Ontario homes, understanding how wind, rain, and snow interact with different materials.
His philosophy is simple: "Build it right the first time, and you never have to apologize for it." This commitment to excellence is the driving force behind every Ollie's Roofing crew member.
A Pillar of the Community
We live here, we work here, and we raise our families here.
Ollie’s Roofing is proud to support local initiatives and give back to the communities that have supported us for 18 years.
When you choose us, you are choosing a local partner dedicated to the long-term well-being of our region.
Experience the Difference Integrity Makes.
Don't trust your home to just anyone. Partner with the company that has earned Ontario's trust for 18 years.
MEET THE CREW
The People Protecting Your Home.
Mark
Ollerenshaw
Founder & CEO
Mike
Rego
Sales Manager
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
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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. 18+ 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