Siding, Windows, & Doors in Oakville, ON | Gerry's Roofing & Siding

First impressions start outside, and after enough Ontario winters, the wear has a way of catching up. A tired roof, drafty windows, and fading siding can change how your home looks and feels before you even realize it. The good news? The right exterior work changes everything, including how it holds up through the seasons and how comfortable it feels inside.

Gerry's Roofing & Siding has been the company to call for Oakville homeowners for over 45 years. Your home's exterior is worth investing in, and we'll make sure the results back that up.

Roofing, Siding, Windows, & More

One of the things our customers appreciate most is not having to juggle multiple contractors. We handle every part of your home's exterior, so you deal with one team, one process, and one point of contact.

Roofing: A solid roof is the foundation of everything else. We work with asphalt, flat, and metal systems, and we’ll help you figure out whether a repair or full replacement is the smarter move.

Siding: New siding is one of those upgrades that surprises people with how much it changes things. We carry durable materials from James Hardie and Royal in plenty of colours.

Windows: If your windows are letting cold air in or driving up your energy bill, it's time to replace them. Our energy-efficient options improve comfort, reduce drafts, and let in more natural light.

Doors: Your front door gets more use than almost anything else in your home. We install entry and patio doors that look great, stand up over time, and provide the security you need.

Gutters: Most people don't think about their gutters until something goes wrong. We install quality gutter systems with Alu-Rex gutter guards so water keeps moving, and debris stays out.

Skylights: Some rooms just need more light, and a skylight or sun tunnel is the best way to get it. It's an addition that tends to have a bigger impact on a space than most homeowners expect.

We've handled just about every exterior challenge you can imagine. Whatever you're dealing with, we've handled it before, and we'll bring that same experience to your home.

What to Expect From Day One

Tackling a project like this can feel overwhelming. We get it. That's why our process is set up to be straightforward, so you always know what's happening and what to expect next.

Here’s a closer look:

Tell us what you're thinking. We’ll start with a no-obligation quote specific to your home, not a generic number pulled out of thin air. Bring your ideas, your wish list, and your budget, and we'll build a plan around all three.
We'll help you find what you love. With a variety of Canadian manufacturers to choose from, including IKO, Euroshield, Ontario Metal Products, Royal, James Hardie, Del, Velux, Alu-Rex, and Gentek, there's no shortage of options.
Leave the rest to us. Our technicians show up on time, work carefully, and respect your property. We’ll also protect your home throughout the process, keep things tidy, and won't consider the job finished until you're satisfied.

When everything goes the way it should, the only thing you'll regret is not doing it sooner.

Why Choose Gerry's Roofing & Siding?

There are many contractors to choose from in Oakville, ON. So what makes one worth trusting with your home? For us, it comes down to a track record that's been built job by job, neighbourhood by neighbourhood, over more than four decades.

When you work with us, here's what you get:

45+ years of local experience in Oakville and surrounding communities
30,000+ completed projects with consistent, proven results
A Transferable Lifetime Workmanship Guarantee for long-term peace of mind
A structured process that keeps things on track and on time
A reputation backed by reviews, industry awards, and repeat business

We've built our business one happy customer at a time. That's not something we take for granted, and it's exactly the kind of experience we aim to deliver every single time.

A Standard Built Over Decades

Awards are nice, but the real measure of a company is what customers say after the job is done. We're proud to have both.

Over the years, we've earned an A+ Better Business Bureau rating, the HomeStars Best of Award, ThreeBestRated recognition, and plenty of kind words from Oakville homeowners on Google. But at the end of the day, what truly reflects who we are is how we handle each project.

We’re committed to providing clear quotes, honest timelines, and thorough cleanup once the work is done. For larger projects, we also offer payment plans to make the cost more manageable. That's the standard we hold ourselves to.

Familiar Streets. Proven Results

Oakville isn't just an area we service. It's where we work, where we've built our reputation, and where many of our customers have become returning ones over the years.

We know the neighbourhoods well, from Morrison and Ford Drive to Glenorchy, West Oakville, River Oaks, Joshua Creek, and Bronte, and we understand the architectural styles and material expectations that come with homes in this city. We also factor in local conditions, such as seasonal weather, snow loads, and how different materials perform here over time.

Wondering if we service your neighbourhood? Head to our service areas page to learn more.

Frequently Asked Questions

How do I know if my home needs a new roof, windows, or siding?
Keep an eye out for leaks, noticeable drafts, climbing energy bills, or visible wear on the outside of your home. When in doubt, just call us. We’d be happy to assess what's going on!

What kind of warranties do you offer?
We provide a Transferable Lifetime Workmanship Guarantee for the original homeowner, with coverage extending up to 20 years to the next owner.

Do you work year-round in Oakville?
Yes! Our specialists stay active year-round and adjust their approach to conditions to ensure quality and safety are never compromised.

Can you match new siding or windows to my home's existing style?
Absolutely. Whether your home leans modern or more traditional, we’ll help you find options that feel like they've always been there.