The best roofing companies in Milton in 2026 are Pro House Maintenance, Ollie's Roofing and The Roof Medic, followed by four more well-rated local roofers. Our Google Maps search found 80 roofing businesses for Milton, but only 6 Milton roofers met our bar of 4.5 stars from 10 or more reviews. Re-roofing a newer detached Milton home costs $15,000 to $27,000 in 2026, according to a Halton Region price guide.
- Only 6 of the 80 businesses our Milton roofing search found met our bar of 4.5 stars from 10 or more reviews.
- Just 12 Milton-based businesses list both a roofing category and a website on Google Maps.
- The 6 ranked Milton roofers hold Google ratings of 4.7 to 4.9, from 29 to 359 reviews each.
- Re-roofing a newer detached Milton home with 2,200 to 3,200 sq ft of roof costs $15,000 to $27,000 in 2026.
- Small roof repairs in Halton Region, such as lifted shingles or new flashing, cost $450 to $1,800.
| 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 Milton |
| 2 | Ollie's Roofing Ltd. | 24/7 roofing help since 2008 | Founded 2008, Insurance stated (company-stated) | 4.9 (359 reviews) | Milton |
| 3 | The Roof Medic | Family-run repairs and flat roofs | Insurance stated, WSIB stated (company-stated) | 4.9 (168 reviews) | Milton |
| 4 | Marios Roofing | Round-the-clock emergency repairs | None stated on its website | 4.9 (80 reviews) | Milton |
| 5 | The Roof Whisperer of Milton | Skylight repairs and installations | None stated on its website | 4.9 (29 reviews) | Service area only |
| 6 | Done Right Roofing & Sheet Metal | GAF Master Elite roof replacements | GAF Master Elite, WSIB stated (company-stated) | 4.7 (96 reviews) | Campbellville |
| 7 | Expert Roofing | Owner-run jobs with a 10-year warranty | Founded 2009, Insurance stated (company-stated) | 4.7 (49 reviews) | Milton |
Who are the best roofing companies in Milton in 2026?
The best roofing companies in Milton in 2026 are Pro House Maintenance, Ollie’s Roofing and The Roof Medic. Marios Roofing, The Roof Whisperer, Done Right Roofing and Expert Roofing complete the top seven. The six ranked roofers hold Google ratings of 4.7 to 4.9 from 29 to 359 reviews, and our free matching service ranks first.
1. Pro House Maintenance: best for comparing vetted roofing companies for free
Pro House Maintenance is a free service that matches Milton homeowners with roofers we have already checked. You describe the job once, and we connect you with roofers who passed WSIB, insurance, reference and background checks. You compare several written quotes, choose who to hire, and our satisfaction guarantee backs the work.
Milton is a small roofing market. Our search turned up just 12 Milton-based roofers with a website, and only 6 met our rating bar. We match you with vetted roofers who serve your part of Milton, so you can compare written quotes side by side.
- 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. Ollie's Roofing Ltd.: best for 24/7 roofing help since 2008
- Google rating 4.9 from 359 reviews checked Oct 2, 2026
- Founded 2008 company website
- Based in Milton
- Visit the Ollie's Roofing Ltd. website
Ollie’s Roofing is a family-run Milton roofer on Steeles Avenue East that has worked since 2008, its website says. It holds a 4.9 Google rating from 359 reviews, the most on this list. The site lists a 24/7 phone line, emergency tarping and standing seam metal roofs, plus liability insurance and WSIB coverage.
- Strengths: It also works in Muskoka and Parry Sound, which helps if you own a cottage there.
- Watch-outs: We found no workmanship warranty length on its website, so ask for it in writing.
- Best for: Leaks and storm damage that cannot wait.
3. The Roof Medic: best for family-run repairs and flat roofs
- Google rating 4.9 from 168 reviews checked Oct 2, 2026
- Based in Milton
- Visit the The Roof Medic website
The Roof Medic is a family-owned roofing company on Laurier Avenue in Milton. It holds a 4.9 Google rating from 168 reviews. Its website says the company is WSIB certified and fully insured, offers emergency roof repairs and flat roofs, and also serves Oakville, Mississauga, Brampton and Etobicoke.
- Watch-outs: We found no warranty terms or founding year on its website, so ask for both before you sign.
- Best for: Repairs and flat roofs in Milton and nearby towns.
4. Marios Roofing: best for round-the-clock emergency repairs
- Google rating 4.9 from 80 reviews checked Oct 2, 2026
- Warranty Product and craftsmanship warranty company website
- Based in Milton
- Visit the Marios Roofing website
Marios Roofing is a Milton roofer on Fitzgerald Crescent. It holds a 4.9 Google rating from 80 reviews. Its website says its roofers are on call around the clock for emergency repairs and same-day service. It serves Mississauga, Brampton, Burlington, Oakville, Georgetown and Halton Hills, and it offers product and craftsmanship warranties.
- Watch-outs: The site names its warranties but gives no length, so ask for the terms in writing.
- Best for: Urgent repairs outside business hours.
5. The Roof Whisperer of Milton: best for skylight repairs and installations
- Google rating 4.9 from 29 reviews checked Oct 2, 2026
- Warranty Written Ironclad Workmanship Warranty company website
- Based in Service-area business (no public street address)
- Visit the The Roof Whisperer of Milton website
The Roof Whisperer runs this Milton listing, and its website describes the company as Toronto based. It holds a 4.9 Google rating from 29 reviews. The site lists skylight work, flat roofs, and asphalt, cedar, slate and metal roofs. It promises a written Ironclad Workmanship Warranty and says it works directly with insurance companies.
- Watch-outs: Its Google listing shows no street address, so ask where the crew is based and who will do your job.
- Best for: Leaky skylights and skylight replacements.
6. Done Right Roofing & Sheet Metal: best for GAF Master Elite roof replacements
- Google rating 4.7 from 96 reviews checked Oct 2, 2026
- Warranty GAF Golden Pledge: up to 50 years material, up to 25 years workmanship company website
- Certification GAF Master Elite company website
- Based in Campbellville
- Visit the Done Right Roofing & Sheet Metal website
Done Right Roofing & Sheet Metal is based on Guelph Line in Campbellville, a village within Milton. It holds a 4.7 Google rating from 96 reviews. Its website cites over 30 years of experience and GAF Master Elite status, says all team members are covered by WSIB, and offers financing.
- Strengths: The site offers the GAF Golden Pledge warranty, which it says covers up to 50 years of materials and up to 25 years of workmanship.
- Watch-outs: Those warranty figures are “up to” amounts, so confirm what your roof qualifies for.
- Best for: Full replacements where warranty length matters.
7. Expert Roofing: best for owner-run jobs with a 10-year warranty
- Google rating 4.7 from 49 reviews checked Oct 2, 2026
- Founded 2009 company website
- Warranty 10-Year Workmanship Warranty company website
- Based in Milton
- Visit the Expert Roofing website
Expert Roofing is a family-owned Milton roofer on McNabb Crescent that has worked since 2009, its website says. It holds a 4.7 Google rating from 49 reviews. The site says the owner handles every project, with no commissioned salespeople or subcontracted crews. It states $5 million in liability insurance, WSIB coverage and a 10-year workmanship warranty.
- Watch-outs: The site lists “every required trade certification” without naming them, so ask which ones apply to your roof.
- Best for: Homeowners who want to deal with the owner from quote to final check.
How much does a new roof cost in Milton?
Re-roofing a newer detached Milton home costs $15,000 to $27,000 in 2026, according to a Halton Region price guide. Architectural shingles cost $6.00 to $9.00 per square foot installed, and standing seam metal costs $16.00 to $26.00. Small repairs, such as lifted shingles or a resealed chimney flashing, cost $450 to $1,800.
| Job | Typical cost (CAD) | Source |
|---|---|---|
| Newer Milton detached (2,200 to 3,200 sq ft of roof) | $15,000 to $27,000 | The Roof Technician, 2026 |
| Semi-detached or freehold townhouse (900 to 1,400 sq ft) | $6,500 to $11,500 | The Roof Technician, 2026 |
| Architectural asphalt shingles, per sq ft | $6.00 to $9.00 | The Roof Technician, 2026 |
| Standing seam metal, per sq ft | $16.00 to $26.00 | The Roof Technician, 2026 |
| Small repair (lifted shingles, flashing) | $450 to $1,800 | The Roof Technician, 2026 |
| Valley rebuild or deck section after a leak | $1,800 to $4,500 | The Roof Technician, 2026 |
Milton’s housing explains the high end. The guide says much of Milton was built since the early 2000s, and homes from about 2003 on tend to have steeper pitches and more roof planes. It adds that many of these homes now need their first new roof, and that homes up on the escarpment catch stronger gusts.
For lifespan and storm data across North America, see our 2026 roofing statistics guide. When you are ready to price your own roof, request free roofing quotes in Milton.
How do you choose a roofing company in Milton?
Choose a Milton 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 recommends 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 Milton 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’s advice is short: “Always get at least 3 written estimates from different contractors.” In Milton, only 6 local roofers met our rating bar, so three quotes means calling half of this list. Read the full checklist on Ontario’s home renovation rights page.
Pro House Maintenance runs the WSIB, insurance, reference and background checks before we match a roofer with you, so the quotes you get are already screened. If a leak has already stained a ceiling, compare water damage restoration in Milton while the roof gets fixed.
How did we rank these Milton roofing companies?
We ranked Milton roofers on public data, and no company paid for a spot. Our Google Maps search for Milton found 80 businesses, but only 21 list roofing as their main category. Just 12 of those are Milton roofers with a website, and 6 hold 4.5 stars or more from 10 or more reviews.
| Step | Businesses remaining |
|---|---|
| Found on Google Maps | 80 |
| Primary Google category is a roofing company | 21 |
| Open, with a website of its own | 12 |
| In Milton (by address or Google map pin) | 12 |
| 4.5+ stars from 10+ Google reviews | 6 |
| Listed on this page (top ranked) | 6 |
That is why this list has 6 roofers instead of 7: we list every Milton roofer that met the bar. The score blends each rating with its review count, so a 4.9 from 29 reviews edges a 4.7 from 96. We checked every fact on October 2, 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 Milton, Timberlea, Dempsey, Willmott and Hawthorne Village. See an error? Please tell our editors about it and we will review it.
What do Milton homeowners ask before they re-roof?
Milton homeowners ask what a new roof costs, whether a repair will do, and how many good local roofers there are. These answers use a 2026 Halton Region price guide, our own Milton research and Ontario consumer advice. Every answer works on its own, so start with the question closest to yours.
How much does a new roof cost in Milton?
Re-roofing a newer detached Milton home with 2,200 to 3,200 square feet of roof costs $15,000 to $27,000 in 2026, according to a Halton price guide. A semi or townhouse roof costs $6,500 to $11,500. Architectural shingles run $6.00 to $9.00 per square foot installed, and steep pitches push the price up.
Should I repair or replace my roof in Milton?
Repair a young roof with damage in one spot. A 2026 Halton price guide says targeted repairs make the most sense on roofs under 15 years old, and small fixes cost $450 to $1,800. Once a roof is past 20 years, sheds granules widely and needs a third repair, the guide says to replace it.
How many good roofers are there in Milton?
By our count, 6 Milton-based roofers meet our bar. Our Google Maps search found 80 businesses, but only 12 were Milton roofers with a website, and 6 of those held 4.5 stars or more from 10 or more reviews. Several roofers on our Mississauga and Hamilton lists also name Milton as a service area.
Do roofers need a licence in Milton?
Ontario does not license roofing contractors, so there is no provincial roofing licence to look up. Instead, confirm a current WSIB clearance, ask for proof of liability insurance and call at least three references. Before work starts, ask the Town of Milton whether your project needs a building permit.
Is Pro House Maintenance free for Milton homeowners?
Pro House Maintenance is free for homeowners. You describe your roof job once, and we match you with several roofers who passed WSIB, insurance, reference and background checks. You compare their written quotes and decide who to hire. Our satisfaction guarantee backs work from the roofers we match.
Where can you find roofing companies near Milton?
The closest roofing companies lists to Milton cover Oakville (16 km away), Mississauga (20 km away) and Hamilton (29 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.
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