Roofs in Windsor-Essex live a hard life. The region is flat and open, so wind coming off Lake St. Clair and Lake Erie hits roofs with nothing to slow it down, and gusts over 90 km/h show up a few times every year. Add summer thunderstorms with hail, winter freeze-thaw cycles that lift and reseal shingles dozens of times a season, and humid summers that cook asphalt, and a shingle roof that is rated for 30 years often needs replacing at 18 to 22.
The housing stock matters too. Steep-pitched century homes in Walkerville, Olde Walkerville and Sandwich Town often have two or even three layers of old shingles and original plank decking that needs partial replacement when it is exposed. Post-war bungalows in South Windsor and Forest Glade have low slopes and long overhangs where ice dams form when attic insulation is thin. Newer homes in LaSalle, Tecumseh and Lakeshore have more complex rooflines with valleys and dormers where flashing failures start. A roofer who works these neighbourhoods every week quotes the right roof the first time.
A legitimate roofing contractor in Ontario carries WSIB coverage for every person on your roof and at least $2 million in liability insurance. Fall protection is mandatory under the Occupational Health and Safety Act, and if you see a crew without harnesses, that tells you something about the rest of their work. Permits are not usually required for a like-for-like reshingle in Windsor, but structural changes, new skylights or converting a flat roof may need one. We confirm insurance and WSIB before any roofer joins our network.
Describe your roof using the form on this page: roof type, approximate age, number of storeys and whether you have an active leak. We match you with a local roofer who can come out, inspect and give you a written quote, free and with no obligation.
Common roofing jobs we arrange
- ▸Asphalt shingle roof replacement
- ▸Metal roofing (standing seam and metal shingle)
- ▸Flat roof replacement (modified bitumen, TPO, EPDM) for additions and garages
- ▸Leak detection and repair
- ▸Storm, wind and hail damage repair with insurance documentation
- ▸Flashing, chimney and skylight resealing or replacement
- ▸Roof decking and plywood replacement
- ▸Attic ventilation upgrades (ridge vents, soffit vents)
- ▸Ice dam prevention and ice and water shield installation
- ▸Eavestrough, fascia and soffit replacement
- ▸Roof inspections for home purchases and insurance
- ▸Emergency tarping after storm damage
Typical costs (2026)
Ballpark ranges from recent local jobs. Your quote depends on the scope, materials and access. Get an exact number with a free quote.
| Job | Typical range | What drives the price |
|---|---|---|
| Asphalt shingle replacement, bungalow (approx. 1,500 sq ft roof area) | $7,500 – $13,500 | Architectural shingles, tear-off of one layer, ice and water shield at eaves, new underlayment and vents. |
| Asphalt shingle replacement, two-storey (approx. 2,500 sq ft roof area) | $12,000 – $22,000 | Steep pitch, multiple layers, valleys and dormers push the top end. |
| Metal roof, standing seam (approx. 1,800 sq ft) | $28,000 – $55,000 | Metal shingle systems are typically 20 to 30 percent less than standing seam. |
| Flat roof replacement (modified bitumen or TPO, 500-800 sq ft) | $5,500 – $13,000 | Insulation upgrades and wet decking replacement are the usual extras. |
| Roof leak repair (flashing, pipe boot, small shingle section) | $400 – $1,500 | Chimney reflashing and skylight replacement are $1,200 to $4,000. |
| Plywood decking replacement (per 4x8 sheet, during a reroof) | $90 – $160 | Century homes with plank decking may need full sheeting over the planks, $2,500 to $6,000 extra. |
| Eavestrough, soffit and fascia replacement (average bungalow) | $3,000 – $7,500 | Aluminum is standard. Leaf guards add $1,000 to $2,500. |
| Emergency tarping after storm damage | $350 – $900 | Often reimbursed by your insurer as emergency mitigation. Keep the invoice. |
Why hire a local pro
- ✔Installs for wind. Local roofers use six nails per shingle and high-wind-rated starter strips as standard, because they have seen what a Lake St. Clair gale does to a four-nail roof.
- ✔Knows the century-home realities: multiple layers to tear off, plank decking that needs sheeting, and steep pitches that require more safety setup.
- ✔Understands ice damming on low-slope bungalows and will recommend ice and water shield well past the code minimum at eaves and valleys.
- ✔Is around after a storm. When wind damage hits half of Riverside at once, a local company with a Windsor address shows up for repairs and insurance paperwork, not a storm-chaser from out of province.
- ✔Carries WSIB and fall-protection compliance, which matters more on roofing than any other trade.
Ready to get quotes?
Tell us about the job in about 2 minutes. We'll match you with a vetted local pro and you'll hear back fast. Free, no obligation.
Roofing FAQs
How long does a shingle roof last in Windsor-Essex?
Expect 18 to 25 years from architectural asphalt shingles, less than the 30 years on the package. Lake wind, hail, humid heat and repeated freeze-thaw cycles all shorten shingle life here. South- and west-facing slopes age fastest. Metal roofs last 40 to 60 years.
Can I put new shingles over the old ones?
The Ontario Building Code allows a second layer in some cases, but almost no reputable Windsor roofer recommends it. You cannot inspect or replace damaged decking, the roof traps heat, and the weight on an older home is a concern. Many homes in Walkerville and Sandwich Town already have two layers and need a full tear-off.
Do I need a permit to replace my roof in Windsor?
Not for a like-for-like reshingle. You do need a permit if you are changing the structure, adding skylights or dormers, or changing the roof covering in a way that changes the load (for example, adding a heavy tile roof). Your contractor should know and handle this.
Will my insurance cover storm damage?
Sudden wind and hail damage is usually covered under a standard Ontario homeowner policy, subject to your deductible. Gradual wear, neglected maintenance and old age are not. Take photos as soon as it is safe, get the roof tarped to prevent further damage, and ask the roofer for a written damage report before you call your insurer. Be wary of anyone offering to waive your deductible, which is a common storm-chaser tactic.
What time of year is best to replace a roof?
Late spring through fall. Shingles seal properly when it is above about 5 to 10 degrees Celsius. Late fall is busy because everyone wants it done before winter, so booking in summer often gets you a better schedule. Emergency repairs happen year-round.
How do I know if a roofer is legitimate?
Ask for a WSIB clearance certificate, a certificate of liability insurance naming you as the certificate holder, a written quote with the shingle brand and product line, underlayment type, ice and water shield coverage, ventilation plan, and a workmanship warranty. A local address and a history of jobs you can drive past matter. Do not pay large deposits for materials; most suppliers deliver on account to established roofers.
What causes ice dams and how do I stop them?
Warm air leaking from the house into the attic melts snow on the roof, which refreezes at the cold eave and backs up under the shingles. The real fix is attic insulation and air sealing, plus proper soffit and ridge ventilation. During a reroof, ice and water shield should extend at least 900 mm up from the eave, and further on low-slope bungalows.
Are metal roofs worth it in Windsor-Essex?
For a home you plan to keep 20 years or more, often yes. Metal sheds snow, resists wind uplift better than shingles, and lasts two to three times as long. The upfront cost is two to three times a shingle roof, and installation quality matters more than with shingles, so choose a roofer who does metal regularly.
Roofing Contractors by area
Roofing guides
- How Much Does a Roof Replacement Cost in Windsor, Ontario? (2026 Prices)
2026 roof replacement costs for Windsor-Essex homes: asphalt, metal and flat roofs by house size, what drives the price up, and how to compare quotes.
- 12 Signs You Need a New Roof (and What Lake Wind and Hail Do to Windsor-Essex Homes)
How to tell whether your roof needs repair or replacement, what wind, hail and freeze-thaw damage look like, and when to call your insurer.