How Much Does a Roof Replacement Cost in Windsor, Ontario? (2026 Prices)

A new asphalt shingle roof on a typical Windsor bungalow costs $7,500 to $13,500 in 2026. A two-storey home runs $12,000 to $22,000, and a standing-seam metal roof is $28,000 to $55,000. Those numbers are for Windsor-Essex specifically, which prices a bit below the GTA for labour and about the same for materials.

Here is where those figures come from, what pushes a quote to the high end, and how to tell a fair quote from a bad one.

Roof replacement cost by home type in Windsor-Essex

Roofers price by the “square” (100 sq ft of roof area), and the roof area is always larger than the floor area because of pitch and overhangs. A 1,200 sq ft bungalow footprint usually has a 1,500 to 1,700 sq ft roof.

Home type	Approx. roof area	Asphalt shingles	Metal (standing seam)
Post-war bungalow (South Windsor, Forest Glade, Roseland)	1,400 to 1,800 sq ft	$7,500 to $13,500	$26,000 to $42,000
Side-split or raised ranch (Fontainebleau, Devonshire Heights)	1,600 to 2,000 sq ft	$9,000 to $15,500	$30,000 to $48,000
Two-storey, 1990s to 2010s (East Riverside, LaSalle, Tecumseh)	2,000 to 2,800 sq ft	$12,000 to $22,000	$38,000 to $60,000
Steep century home (Walkerville, Sandwich Town, Ford City)	1,800 to 2,600 sq ft	$13,000 to $26,000	$40,000 to $65,000
Flat roof section (addition, garage, 500 to 800 sq ft)	500 to 800 sq ft	$5,500 to $13,000 (modified bitumen or TPO)	n/a

All of these are estimates. A written quote after an on-roof inspection is the only real number.

What is included in a proper quote

A legitimate Windsor roofing quote for asphalt shingles should list:

• Tear-off and disposal of the existing roof (one layer; extra layers cost more)
• Inspection and replacement of damaged decking, priced per sheet
• Ice and water shield at the eaves, valleys and around penetrations
• Synthetic underlayment over the rest of the deck
• Drip edge, new flashing at walls and chimneys, new pipe boots
• Architectural shingles with the brand and product line named
• Ridge vent or other ventilation plan
• Six-nail installation (not four) because of local wind
• Clean-up, magnet sweep for nails, and a workmanship warranty (10 years is common from established companies)

If a quote is a single line that says “reshingle roof” and a price, you cannot compare it to anything.

Why Windsor roofs cost what they cost

Wind. Windsor-Essex is flat and open, and gusts over 90 km/h come off Lake St. Clair and Lake Erie several times a year. Good local roofers use high-wind starter strips and six nails per shingle as standard. That adds a bit of labour and material and is worth every dollar.

Layers. Many homes in Walkerville, Sandwich Town and Ford City have two or three layers of old shingles. Each extra layer adds roughly $1,000 to $2,500 in tear-off labour and disposal.

Decking. Century homes were built with plank decking with gaps between boards. Modern shingles need a solid surface, so roofers often have to sheet over the planks with plywood, which adds $2,500 to $6,000. Even on newer homes, expect two to six sheets of plywood to be replaced around chimneys and valleys where leaks have rotted the deck, at $90 to $160 per sheet.

Pitch and complexity. A simple gable bungalow is fast. A steep 12/12 Victorian roof with dormers, or a 2000s two-storey with six valleys, takes two to three times the labour.

Access. Tight Walkerville lots where the bin cannot get close to the house, or two-storey homes with no place to drop debris, slow the crew down.

Disposal. Tipping fees at Essex-Windsor Solid Waste Authority sites have climbed steadily, and shingles are heavy. A typical bungalow produces 3 to 5 tonnes of waste.

Asphalt vs. metal in Windsor-Essex

Architectural asphalt shingles are the default here and for good reason: the price is right and installers are plentiful. But they rarely reach their 30-year rated life in this climate. Between lake wind, hail, humid heat and dozens of freeze-thaw cycles each winter, 18 to 25 years is realistic.

Metal costs two to three times as much upfront and lasts 40 to 60 years. It sheds snow, resists wind uplift better than shingles, and is the better choice for exposed lakefront homes in Riverside, Tecumseh, Belle River and Kingsville. For a house you plan to keep 20 years or more, the math often works. If you expect to sell within 10 years, shingles are the sensible pick.

Metal shingle systems, which look like slate or shakes, sit in between at roughly 20 to 30 percent less than standing seam.

Do you need a permit?

Not for a like-for-like reshingle in the City of Windsor or the county municipalities. You do need a permit if you are changing the structure, adding skylights or dormers, or switching to a heavier covering like tile. Your roofer should know and handle it.

Will insurance pay for it?

If the roof is simply old, no. If a storm tore shingles off or hail cracked them, your Ontario homeowner policy likely covers sudden damage less your deductible. Document everything with photos, get the roof tarped (usually $350 to $900 and typically reimbursed as emergency mitigation), and have the roofer write a damage report before you call your insurer. Be careful of out-of-town companies that show up after a storm offering to “waive your deductible.” That is a red flag and in many cases insurance fraud.

How to get a fair price

1. Get two or three written quotes with the line items above.
2. Check WSIB and insurance. Ask for a WSIB clearance certificate and a certificate of liability insurance. Roofing is the most dangerous trade on your property, and if someone falls and the company is not covered, you can be on the hook.
3. Look for a local address and local jobs. A company that has roofed homes on your street will still be around in year eight when a pipe boot fails.
4. Avoid big deposits. Established roofers get materials on account from suppliers. A 10 percent deposit to hold a date is reasonable; 50 percent is not.
5. Book in summer if you can. Late fall is the busiest season and prices and wait times reflect it.

Ready for quotes?

We match Windsor-Essex homeowners with insured, WSIB-covered roofing contractors who work your neighbourhood every week. Tell us your roof type, age and whether there is an active leak, and get a free inspection and written quote with no obligation. Get free roofing quotes.