The best roofing companies in Oakville in 2026 are Pro House Maintenance, Peace of Mind Exteriors and Cover GTA Roofing, then five more top-rated local roofers. Our Google Maps search found 88 roofing businesses for Oakville. Only 22 were Oakville roofers with a website and 4.5 stars from 10 or more reviews. Most Oakville homeowners pay $9,000 to $17,000 to replace an asphalt shingle roof, a 2026 local guide says.
- Only 22 of the 88 businesses our Oakville roofing search found met our bar of 4.5 stars from 10 or more reviews.
- All 7 ranked Oakville roofers hold a 5.0 Google rating, from 37 to 147 reviews each.
- Most Oakville homeowners pay $9,000 to $17,000 to replace an asphalt shingle roof in 2026.
- Steep, cut-up Oakville roofs with valleys and dormers cost $9.00 to $13.00 per square foot installed.
- Ontario does not license roofers, so WSIB clearance, insurance and 3 written quotes are the checks that count.
| Rank | Company | Best for | Credentials | Google rating | Based in |
|---|---|---|---|---|---|
| 1 | Pro House Maintenance | Comparing vetted roofing companies for free | Every pro: licences, WSIB, insurance, references, background | Not applicable (matching service) | Serves Oakville |
| 2 | Peace of Mind Exteriors | In-house crews and a lifetime workmanship warranty | WSIB stated (company-stated) | 5.0 (147 reviews) | Oakville |
| 3 | Cover gta roofing inc. | Cedar, slate and flat roofs | None stated on its website | 5.0 (66 reviews) | Oakville |
| 4 | Trusted Pro Roofers | Roof financing across Halton and Peel | None stated on its website | 5.0 (66 reviews) | Oakville |
| 5 | The Roof Technician Oakville | Skylights and 24/7 leak repair | Certified Velux installers, Founded 2005 (company-stated) | 5.0 (60 reviews) | Oakville |
| 6 | A-ONE Roofing | Free inspections and a 15-year labour warranty | WSIB stated (company-stated) | 5.0 (44 reviews) | Oakville |
| 7 | Easy Roofing | A 25 year warranty from a firm dating to 1978 | Founded 1978, WSIB stated (company-stated) | 5.0 (44 reviews) | Oakville |
| 8 | Everlast Roofing & Exteriors Inc. | Financing and $5 million liability cover | Founded 1998, Insurance stated (company-stated) | 5.0 (37 reviews) | Oakville |
Who are the best roofing companies in Oakville in 2026?
The best roofing companies in Oakville in 2026 are Pro House Maintenance, Peace of Mind Exteriors and Cover GTA Roofing. Trusted Pro Roofers, The Roof Technician, A-ONE Roofing, Easy Roofing and Everlast Roofing and Exteriors complete the top eight. All seven ranked roofers hold a 5.0 Google rating.
1. Pro House Maintenance: best for comparing vetted roofing companies for free
Pro House Maintenance is our free matching service, and it ranks first because it does the screening for you. Roofers we match in Oakville have passed WSIB, insurance, reference and background checks. You describe the roof once, get several written quotes and choose the one you want. Our satisfaction guarantee covers the roofer you hire.
Oakville has a deep bench of rated roofers. Our searches found 88 businesses, and 22 Oakville roofers held 4.5 stars from 10 or more reviews. With every pick at 5.0, review count set the order, so ask each one for recent Oakville references.
- Trade licences. Ontario does not license roofing contractors, so for roofers the checks below (WSIB, insurance, references and background) carry the weight.
- WSIB clearance and liability insurance. We confirm a current WSIB clearance and commercial general liability insurance before a pro joins our network.
- Reviews and references. We read public reviews and speak with past clients before a pro is accepted, looking for patterns, not one-off complaints.
- Background checks. We run background checks before a pro is matched with homeowners, because the people in your home matter as much as the work.
- Tell us about the job. Share the project and your address through the free quote form. It takes about a minute.
- Get matched with vetted pros. We match you with several pros who have already passed our checks and serve your area.
- Compare written quotes. Each pro gives you a written quote, so you can compare price, scope and timing side by side.
- Hire with a guarantee behind you. You choose who to hire. Work from a pro we matched you with is backed by our satisfaction guarantee; ask us for the terms before you sign.
2. Peace of Mind Exteriors: best for in-house crews and a lifetime workmanship warranty
- Google rating 5.0 from 147 reviews checked Oct 11, 2026
- Warranty Lifetime workmanship warranty company website
- Based in Oakville
- Visit the Peace of Mind Exteriors website
Peace of Mind Exteriors is a York Street roofer in Oakville with a 5.0 Google rating from 147 reviews. Its website says its in-house crews have worked on Oakville homes for more than 23 years, never using subcontractors. It states WSIB coverage, a lifetime workmanship warranty and financing at 0% for 12 months.
- Watch-outs: Ask what the lifetime workmanship warranty covers and whether it transfers if you sell.
- Best for: A full roof, siding or eavestrough job from one crew.
3. Cover gta roofing inc.: best for cedar, slate and flat roofs
- Google rating 5.0 from 66 reviews checked Oct 4, 2026
- Based in Oakville
- Visit the Cover gta roofing inc. website
Cover GTA Roofing is based on Robinson Street in Oakville and holds a 5.0 Google rating from 66 reviews. Its website lists asphalt, cedar, slate and rubber shingles, flat roofs, dormer removal, inspections, soffit and fascia, and eavestrough work. Google lists it as both a roofer and a siding contractor.
- Watch-outs: We found no warranty terms, founding year or insurance details on its website, so ask for all three in writing.
- Best for: Older homes with cedar or slate roofs.
4. Trusted Pro Roofers: best for roof financing across Halton and Peel
- Google rating 5.0 from 66 reviews checked Oct 11, 2026
- Based in Oakville
- Visit the Trusted Pro Roofers website
Trusted Pro Roofers has an office on Upper Middle Road East in Oakville and a 5.0 Google rating from 66 reviews. Its website offers inspections, repairs and full replacements, and says it can help finance a new roof or repairs that insurance will not cover. It lists Oakville, Burlington, Milton, Mississauga, Brampton, Hamilton and Toronto as service areas.
- Watch-outs: The site promises “one of the best roofing warranties” but gives no terms, so ask for the warranty in writing.
- Best for: Homeowners who want to spread the cost of a new roof.
5. The Roof Technician Oakville: best for skylights and 24/7 leak repair
- Google rating 5.0 from 60 reviews checked Oct 4, 2026
- Founded 2005 company website
- Warranty 50-year non-prorated manufacturer warranties company website
- Certification Certified Velux installers company website
- Based in Oakville
- Visit the The Roof Technician Oakville website
The Roof Technician has provided roofing services since 2005, its website says, and its Oakville location holds a 5.0 Google rating from 60 reviews. The site states WSIB compliance, $5 million in liability insurance and certified Velux skylight installers. It offers 24/7 emergency repair and 50-year non-prorated manufacturer warranties.
- Watch-outs: The 50-year coverage is a manufacturer warranty, so ask separately what the workmanship warranty covers.
- Best for: A leaking skylight or a flat roof section.
6. A-ONE Roofing: best for free inspections and a 15-year labour warranty
- Google rating 5.0 from 44 reviews checked Oct 4, 2026
- Warranty 15-year workmanship warranty company website
- Based in Oakville
- Visit the A-ONE Roofing website
A-ONE Roofing is a Wyecroft Road roofer in Oakville with a 5.0 Google rating from 44 reviews. Its website offers free roof inspections, 24/7 emergency response and a 15-year workmanship warranty. It lists WSIB coverage and $5 million in liability insurance, plus gutter, chimney and skylight work.
- Watch-outs: Ask for the 15-year warranty terms in writing, including what voids them.
- Best for: A free second opinion on whether to repair or replace.
7. Easy Roofing: best for a 25 year warranty from a firm dating to 1978
- Google rating 5.0 from 44 reviews checked Oct 4, 2026
- Founded 1978 company website
- Warranty 25 year warranty company website
- Based in Oakville
- Visit the Easy Roofing website
Easy Roofing lists an office on Lakeshore Road East in Oakville and holds a 5.0 Google rating from 44 reviews. Its website says it has offered quality service since 1978 and gives a 25 year warranty on repair, replacement and inspection work. It also says WSIB coverage is available.
- Watch-outs: The site gives its location as Sandhill Drive in Ancaster, so confirm which office runs your Oakville job.
- Best for: Buyers who want a long written warranty.
8. Everlast Roofing & Exteriors Inc.: best for financing and $5 million liability cover
- Google rating 5.0 from 37 reviews checked Oct 4, 2026
- Founded 1998 company website
- Warranty Warranties on labour and materials company website
- Based in Oakville
- Visit the Everlast Roofing & Exteriors Inc. website
Everlast Roofing and Exteriors is a Wyecroft Road company in Oakville with a 5.0 Google rating from 37 reviews. Its website says it has provided quality service since 1998 and carries $5 million in liability insurance. It offers warranties on labour and materials, plus flexible financing.
- Watch-outs: The site claims both “since 1998” and “40+ years of experience”, so ask how long the company itself has operated, and request warranty terms.
- Best for: A roof plus eavestrough, soffit and fascia work.
How much does a new roof cost in Oakville?
Most Oakville homeowners pay $9,000 to $17,000 in 2026 to replace an asphalt shingle roof with a full tear-off, a local price guide says. Standard roofs cost $5.50 to $9.00 per square foot installed. Steep roofs with valleys and dormers cost $9.00 to $13.00, and metal costs two to three times as much.
| Job | Typical cost (CAD) | Source |
|---|---|---|
| Asphalt shingle roof, full tear-off (most homes) | $9,000 to $17,000 | Silver Oak Roofing, 2026 |
| Bungalow or semi (1,000 to 1,500 sq ft of roof) | $7,000 to $11,000 | Silver Oak Roofing, 2026 |
| Two-storey detached (1,500 to 2,500 sq ft) | $10,000 to $17,000 | Silver Oak Roofing, 2026 |
| Larger or complex home (2,500 to 3,500 sq ft) | $15,000 to $23,000 | Silver Oak Roofing, 2026 |
| Standard roof, per sq ft installed | $5.50 to $9.00 | Silver Oak Roofing, 2026 |
| Metal roof, average Oakville home | $18,000 to $40,000 | Silver Oak Roofing, 2026 |
Roof area drives the total more than house size. The guide notes that a 2,000 sq ft two-storey home might have only 1,300 sq ft of roof, while a bungalow of the same size can have well over 2,000. Extra layers of old shingles also add labour and disposal.
For lifespan and storm data, see our 2026 roofing statistics guide. When you are ready for real prices, get free roofing quotes in Oakville from screened local roofers.
How do you choose a roofing company in Oakville?
Choose an Oakville roofer by checking WSIB clearance, liability insurance and references, then getting at least three written quotes. Ontario does not license roofing contractors, so these checks carry the weight. Ontario law requires a written contract for any home renovation worth more than $50, and the province suggests a deposit of 10% or less.
- Check the licence. Ontario does not license roofing contractors, so the WSIB, insurance and contract checks below matter more. See the province’s advice on hiring a roofer in Ontario.
- Confirm WSIB clearance. Ask for the company’s WSIB account number and confirm a current clearance on WSIB’s free eClearance lookup.
- Ask for proof of liability insurance. A certificate of commercial general liability insurance should name the company that will do the work.
- Ask about city licences and permits. Ask Oakville whether the job needs a municipal licence or building permit before work starts.
- Get it in writing. Under Ontario law, any home renovation contract worth more than $50 must be in writing, and the final price cannot exceed an estimate by more than 10% unless you agree (Ontario consumer protection rules).
- Keep the deposit small. Ontario recommends a down payment of no more than 10%, and never paying in full before the work is done.
Ontario puts it plainly: “Having a written contract is the best way to protect your rights as consumer.” Since all 7 Oakville picks hold a 5.0 rating, compare the written scope line by line. Check that each quote includes ice and water protector, new flashing and clean-up.
Pro House Maintenance runs the WSIB, insurance, reference and background checks before we match a roofer with you. If your eavestroughs are due too, compare gutter installation quotes in Oakville in the same request.
How did we rank these Oakville roofing companies?
We ranked Oakville roofers on public data, and no company paid for a spot. Our Google Maps searches for Oakville found 88 businesses, but only 38 listed roofing as their main category. We kept 22 that are based in Oakville, have a working website and hold 4.5 stars from 10 or more reviews.
| Step | Businesses remaining |
|---|---|
| Found on Google Maps | 88 |
| Primary Google category is a roofing company | 38 |
| Open, with a website of its own | 33 |
| In Oakville (by address or Google map pin) | 33 |
| 4.5+ stars from 10+ Google reviews | 22 |
| Listed on this page (top ranked) | 7 |
The score blends each rating with its review count. All 7 picks hold a 5.0, so a 5.0 from 147 reviews ranks above a 5.0 from 37. We checked every fact on October 4, 2026, and we recheck the list every 90 days.
Company website facts are quoted exactly in our research files. The same checks apply in Old Oakville, Glen Abbey, Bronte, River Oaks and Joshua Creek. See an error? Please tell our editors about it and we will review it.
What do Oakville homeowners ask before they re-roof?
Oakville homeowners ask what a new roof costs, whether metal is worth it and how to check a roofer. These answers draw on a 2026 Oakville price guide, our own Oakville research and Ontario consumer rules. Each answer stands alone, so go straight to the question that matches your roof.
How much does a new roof cost in Oakville?
Most Oakville homeowners pay $9,000 to $17,000 in 2026 to replace an asphalt shingle roof with a full tear-off, a local guide says. A typical two-storey detached home runs $10,000 to $17,000. Standard roofs cost $5.50 to $9.00 per square foot, and complex roofs run $9.00 to $13.00.
Is a metal roof worth it in Oakville?
It can be if you plan to stay. A 2026 Oakville guide puts metal at roughly $18,000 to $40,000 on an average home, two to three times the cost of asphalt. It also says metal lasts 40 to 60 years, against 20 to 25 for asphalt shingles.
Do roofers need a licence in Oakville?
Ontario does not license roofing contractors, so there is no provincial roofing licence to check. Confirm a current WSIB clearance, ask for proof of liability insurance and call at least three references. Ask the Town of Oakville whether your job needs a building permit before work starts.
What should an Oakville roof quote include?
A full quote lists tear-off and disposal, ice and water protector, underlayment, new flashing, ventilation and clean-up. The 2026 Oakville guide says skipping ice and water protector or old flashing lowers a quote but brings repairs later. Ontario law also requires a written contract for any home renovation worth more than $50.
How many good roofers are there in Oakville?
By our count, 22 Oakville roofers met our bar. Our searches found 88 businesses, but only 38 had roofing as their main Google category. Of those, 33 had a website and an Oakville location, and 22 held 4.5 stars from 10 or more reviews. We list the top 7.
Is Pro House Maintenance free for Oakville homeowners?
Yes. Pro House Maintenance is free for homeowners. You describe your roof job once, and we match you with several roofers who have passed WSIB, insurance, reference and background checks. You compare their written quotes and choose who to hire, and our satisfaction guarantee backs the work.
Where can you find roofing companies near Oakville?
The closest roofing companies lists to Oakville cover Mississauga (14 km away), Milton (16 km away) and Hamilton (28 km away). Each list follows the same method: 4.5-star Google ratings from 10 or more reviews, official registry checks where Ontario requires a licence, and free vetted matching from Pro House Maintenance at number one.
- Best roofing companies in Mississauga (14 km from Oakville)
- Best roofing companies in Milton (16 km from Oakville)
- Best roofing companies in Hamilton (28 km from Oakville)
- Best gutter companies in Oakville
- Compare free roofing quotes in Oakville from vetted local pros
- Best roofing companies across Ontario, city by city
- Roofing statistics and cost data from our research team