Updated June 2026

Top 10 Roofing Contractors in Milton

Vetted, currently-operating roofing contractors serving Milton and the Halton region, ranked by longevity, manufacturer certifications and verified BBB standing.

Quick Comparison

Rank Company Specialty Experience BBB Website
1 Ollie's Roofing Ltd. Best Overall Since 2008 A+ Accredited Visit
2 Cherry and Clark Roofing Most Trusted Name 40+ Years Listed Visit
3 D'Angelo & Sons Roofing & Exteriors Most Established Since 1978 Listed Visit
4 Maura Roofing Ltd. Top Certified Craftsman Since 1982 Listed Visit
5 Done-Right Roofing & Sheet Metal Local GAF Master Elite 30+ Years Listed Visit
6 Custom Contracting Best Full-Exterior Service Since 2017 Listed Visit
7 Above It All Roofing Best for Flat & Metal Roofs 25+ Years Listed Visit
8 Tops Roofing Veteran Residential & Commercial Since 1987 Listed Visit
9 Tiltop Roofers Inc. Modern Inspection Tech Local Listed Visit
10 Vassa Metal Roofing Metal Roofing Specialist 20+ Years Not Listed Visit

Detailed Reviews

#2

Cherry and Clark Roofing

Most Trusted Name
ExperienceEstablished Local Roofer (40+ Years)
BBB StatusListed
SpecialtyResidential & Commercial
Service AreaMilton & the GTA

Cherry and Clark Roofing Company Ltd. traces its roots back more than 40 years and runs dedicated residential and commercial divisions serving Milton. The firm is a GAF Master Elite certified installer, a credential held by a small fraction of North American roofers that backs eligible installs with stronger manufacturer warranties. Work covers shingle, metal and flat roofing, siding, eavestrough, skylights, insulation and ice-damming, with drone inspections used for assessments.

Roof Replacement Roof Repair Asphalt Shingles Metal Roofing Flat Roofing Eavestrough Skylights Siding
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#3

D'Angelo & Sons Roofing & Exteriors

Most Established
ExperienceSince 1978 (45+ Years)
BBB StatusListed
SpecialtyResidential & Commercial
Service AreaMilton, GTA & Golden Horseshoe

Family-owned and operating since 1978, D'Angelo & Sons is one of the longest-running and broadest exterior contractors serving Milton and the wider Greater Toronto Area. Beyond roof replacement and repair it handles commercial flat roofing, eavestrough, siding, masonry, metal roofs and ice-dam removal, and provides emergency service year-round. The company carries WSIB coverage and reports tens of thousands of completed roofs across the GTA.

Roof Replacement Roof Repair Flat Roofing Eavestrough Siding Metal Roofing Masonry Ice Dam Removal Emergency Service
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#4

Maura Roofing Ltd.

Top Certified Craftsman
ExperienceSince 1982 (40+ Years)
BBB StatusListed
SpecialtyResidential, Commercial & Industrial
Service AreaMilton & Greater Toronto Area

Established in 1982, Maura Roofing brings more than four decades of experience to Milton and surrounding communities. It holds CertainTeed's ShingleMaster and Master Craftsman roofing credentials, among the manufacturer's higher installer designations. Services include new construction, shingle and flat-roof replacement, roof repair, maintenance, inspections, emergency repairs and sheet-metal work for residential, commercial and industrial clients.

Roof Replacement Roof Repair Asphalt Shingles Flat Roofing Sheet Metal Roof Inspection Emergency Repair New Construction
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#5

Done-Right Roofing & Sheet Metal

Local GAF Master Elite
ExperienceEstablished Local Roofer (30+ Years)
BBB StatusListed
SpecialtyResidential & Commercial
Service AreaMilton & Halton Region

Based in the Milton area on Guelph Line, Done-Right Roofing & Sheet Metal has served Milton and the Halton Region for more than 30 years. It is a GAF Master Elite certified contractor, which lets it offer GAF's extended non-prorated warranties, and is fully licensed and WSIB insured. The company handles shingle and flat roofing, sheet-metal work, repairs and replacements for homes and businesses, and was recognized in the Canadian Champion Reader's Choice awards.

Roof Replacement Roof Repair Asphalt Shingles Flat Roofing Sheet Metal Skylights
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#6

Custom Contracting

Best Full-Exterior Service
ExperienceServing Milton Since 2017
BBB StatusListed
SpecialtyResidential & Commercial
Service AreaMilton & Halton Region

Custom Contracting is a GAF roofing contractor that has served Milton homeowners and businesses since 2017 as part of a broader exterior-renovation company headquartered in southern Ontario. It partners with major manufacturers including GAF, CertainTeed and IKO, installing architectural shingles such as GAF's Timberline HDZ line. Alongside roofing it offers windows, siding and other exterior services tailored to the local climate.

Roof Replacement Roof Repair Asphalt Shingles Windows Siding Eavestrough
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#7

Above It All Roofing

Best for Flat & Metal Roofs
ExperienceEstablished Local Roofer (25+ Years)
BBB StatusListed
SpecialtyResidential & Commercial
Service AreaMilton & Halton Region

With more than 25 years of experience, Above It All Roofing serves Milton and neighbouring towns including Acton, Georgetown, Burlington and Oakville. It is a CertainTeed ShingleMaster certified contractor and maintains partnerships with GAF, Elevate, Gentek and Velux. The firm is WSIB covered and fully licensed and insured, handling asphalt, metal and flat (EPDM, TPO, PVC) systems plus eavestrough, leaf guards, fascia, soffit and skylights.

Roof Replacement Roof Repair Asphalt Shingles Metal Roofing Flat Roofing Eavestrough Soffit & Fascia Skylights
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#8

Tops Roofing

Veteran Residential & Commercial
ExperienceSince 1987 (30+ Years)
BBB StatusListed
SpecialtyResidential & Commercial
Service AreaMilton & Southern Ontario

Tops Roofing has installed, repaired and replaced roofs across Southern Ontario since 1987, with founder Brian Burnett bringing more than three decades in the trade. Operating its Milton-focused presence at miltonroofing.ca, the company provides residential and commercial roof installations and replacements, roof repairs, skylight installation and flat roofing, and offers financing options. Its service footprint spans Milton, Oakville, Burlington, Mississauga and the wider region.

Roof Replacement Roof Repair Asphalt Shingles Flat Roofing Skylights
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#9

Tiltop Roofers Inc.

Modern Inspection Tech
ExperienceEstablished Local Roofer
BBB StatusListed
SpecialtyResidential & Commercial
Service AreaMilton & West GTA

Tiltop Roofers, based in Mississauga, markets itself as a go-to roofing team for Milton and the west GTA and states it is professional, licensed and insured. The company emphasizes drone-based roof inspections and offers roof repair, replacement and leak detection along with eavestrough, skylights, soffit and fascia, attic insulation, storm-damage restoration and commercial roofing, plus monthly financing options.

Roof Replacement Roof Repair Eavestrough Skylights Soffit & Fascia Attic Insulation Storm Damage Repair
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#10

Vassa Metal Roofing

Metal Roofing Specialist
ExperienceEstablished Local Roofer (20+ Years)
BBB StatusNot Listed
SpecialtyResidential & Commercial Metal
Service AreaMilton & Surrounding Areas

Vassa Metal Roofing focuses specifically on metal roofing systems and has served Milton clients for over 20 years. Working from a St. Catharines base with a wide service radius, it installs steel roofing, metal tile and metal-shake profiles for both residential and commercial properties and backs residential metal roofs with a limited lifetime warranty. For homeowners prioritizing a long-life metal roof over asphalt, it is the most specialized option on this list.

Metal Roofing Steel Roofing Metal Tile Metal Shake Roof Replacement
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How to Choose a Roofing Contractor in Milton

Confirm WSIB coverage and proper insurance

Ontario has no provincial roofing trade licence, so the single most important verification in Milton is that your contractor carries active WSIB (Workplace Safety and Insurance Board) coverage plus general liability insurance. WSIB protects you from liability if a worker is injured on your roof. Ask for a WSIB clearance certificate and a certificate of insurance before any deposit. Milton-area firms such as Ollie's Roofing and Done-Right Roofing explicitly advertise WSIB coverage.

Verify the municipal building permit process

Full roof replacements that involve structural changes, sheathing replacement or altering the roof framing require a building permit from the Town of Milton's Building Services. A like-for-like re-shingle often does not, but a reputable roofer will know exactly when one is needed and will pull it for you. Be wary of any contractor who tells you to skip a permit when structural work is involved — it can void insurance and complicate a future home sale.

Prioritize manufacturer certifications

Look for credentials like GAF Master Elite (held by Cherry and Clark and Done-Right) or CertainTeed ShingleMaster (held by Maura Roofing and Above It All). These designations require training and good standing with the manufacturer and unlock stronger, longer warranties — important given Milton's freeze-thaw cycles, which stress shingles and sealants over time.

Choose a contractor experienced with Ontario winters

Milton roofs face heavy snow load, ice damming and repeated freeze-thaw. Ensure your contractor installs proper ice-and-water shield membrane along eaves and valleys (Ontario Building Code requires self-adhered membrane at eaves in this climate zone) and addresses attic ventilation and insulation, the root causes of ice dams. Ask specifically how they detail eaves, valleys and roof-wall transitions.

Check local longevity and reputation

A contractor that has worked in Milton and the Halton region for years is more likely to honour its workmanship warranty and still be in business when you need a callback. Several firms here — D'Angelo & Sons (since 1978), Maura Roofing (since 1982) and Tops Roofing (since 1987) — have decades of regional history. Verify standing through BBB profiles (bbb.org serves Canada), the Milton Chamber of Commerce and local review platforms such as HomeStars.

Get detailed written quotes and warranties

Collect at least three written estimates that itemize tear-off, underlayment, ice-and-water shield, ventilation, flashing and disposal — not just a single lump-sum number. Confirm both the manufacturer's material warranty and the contractor's separate workmanship warranty in writing. In Ontario, watch for any door-to-door pressure tactics; a trustworthy Milton roofer provides a written quote and lets you take time to decide.

Frequently Asked Questions

For a typical Milton detached home, an asphalt shingle roof replacement generally runs about CAD $7,000 to $16,000, depending on roof size, pitch, the number of layers torn off and shingle grade. Larger or more complex homes with steep pitches or premium architectural shingles can exceed $20,000. Standing-seam or steel metal roofing costs considerably more — often CAD $18,000 to $40,000+ — but lasts far longer. Always get itemized written quotes, as prices vary with material and access.
Asphalt architectural (laminate) shingles remain the most popular choice in Milton for their balance of cost, durability and winter performance, typically rated for high wind and freeze-thaw. Metal roofing (steel) is an excellent long-life option that sheds snow well and resists ice damming, which is why specialists like Vassa Metal Roofing operate in the area. For the flat or low-slope sections common on additions and commercial buildings, EPDM, TPO or modified-bitumen membranes are standard.
Ontario has no provincial roofing contractor licence — unlike Quebec's mandatory RBQ licence. Instead, your roofer should carry WSIB coverage and liability insurance. A Town of Milton building permit is required when the work involves structural changes, replacing roof sheathing or altering the framing; a straightforward re-shingle usually does not need one. A good local contractor will confirm permit requirements and obtain any permit on your behalf.
In Milton's climate, a quality asphalt shingle roof typically lasts 20 to 30 years, though aggressive freeze-thaw cycles, ice damming and summer heat can shorten that without proper ventilation. Premium architectural shingles and well-ventilated installs reach the upper end. Metal roofs commonly last 40 to 50+ years. Proper attic ventilation, ice-and-water shield and routine maintenance are the biggest factors in reaching a roof's full lifespan locally.
Confirm active WSIB coverage and liability insurance, ask for a written itemized quote and a clear workmanship warranty, and favour contractors with manufacturer certifications such as GAF Master Elite or CertainTeed ShingleMaster. Check their standing on bbb.org (which serves Canada) and the Milton Chamber of Commerce, and choose a firm with a track record in the Halton region. Make sure they detail ice-and-water shield at eaves and address attic ventilation — essentials for an Ontario winter roof.
Ice dams form when heat escaping into the attic melts snow that refreezes at the cold eaves, forcing water back under shingles. In Milton, the fixes are proper attic insulation, balanced soffit-to-ridge ventilation, and a self-adhered ice-and-water shield membrane installed along eaves and valleys (required at eaves under the Ontario Building Code for this climate). If you already see large icicles or interior leaks each winter, have a local roofer inspect ventilation and membrane coverage and arrange professional ice-dam removal rather than chipping at it yourself.

Roofing in Milton

Milton sits at the base of the Niagara Escarpment in Ontario's Halton Region, and its roofs take a beating from a classic Southern Ontario four-season climate. Winters bring sustained sub-zero cold, significant snow load and repeated freeze-thaw cycles as temperatures swing around the freezing mark — the single biggest stressor on local roofs. Snow that melts over a warm attic refreezes at the cold eaves, creating ice dams that push water back under shingles and into the home. Summers add intense UV, heat and the occasional severe thunderstorm or windstorm sweeping off Lake Ontario, so a Milton roof must handle both deep-freeze and high-heat extremes within the same year.

The dominant roofing material across Milton's many subdivisions is the asphalt shingle, with architectural (laminate) shingles now standard on most detached and townhome rebuilds for their wind resistance and longer life. Metal roofing — steel standing-seam and metal-tile or shake profiles — is a growing premium choice prized for shedding snow, resisting ice dams and lasting 40 to 50+ years. Flat and low-slope membrane systems (EPDM, TPO and modified bitumen) appear on home additions, dormers and the town's commercial and industrial buildings. Whatever the covering, local best practice calls for a self-adhered ice-and-water shield at the eaves and valleys, a key defence in this freeze-thaw climate.

On regulation, Ontario differs from some other provinces: there is no provincial roofing-trade licence here — unlike Quebec, where contractors must hold an RBQ licence, or Alberta, which requires a prepaid contractor licence for door-to-door sales. What Ontario does require is that roofing contractors carry WSIB (Workplace Safety and Insurance Board) coverage so you are not liable for on-site worker injuries, plus general liability insurance. At the municipal level, the Town of Milton issues building permits through its Building Services department; a permit is required when a roofing project involves structural work, sheathing replacement or framing changes, while a like-for-like re-shingle typically does not. Reputable local roofers know exactly when a permit applies and will obtain it.

Because Milton's freeze-thaw cycles, snow load and ice damming punish any weak detail, choosing an experienced local contractor matters more here than in milder regions. A roofer who works the Halton area year-round knows how to detail eaves, valleys and roof-wall transitions for Ontario winters, sizes attic ventilation correctly to prevent ice dams, and will still be around to honour a workmanship warranty. The contractors profiled below were selected for verifiable longevity, manufacturer certifications such as GAF Master Elite and CertainTeed ShingleMaster, confirmed BBB standing where available, breadth of services and a demonstrated track record serving Milton and the surrounding Halton Region.

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