Hail, wind and sun are hard on a roof. The best roofing contractors in Waukesha inspect honestly, work with your insurance when a claim is real, and install shingle, metal or tile systems with the underlayment and flashing done right.
Picked by people who read the reviews.
Our review committee researched roofing contractors serving Waukesha and the surrounding area, read consumer reviews across the web, and settled on these five. We look at how many people have reviewed a company, what they say, and how the company holds up over time. We keep the full recipe to ourselves so it cannot be gamed. Google ratings shown are as of November 9, 2026. No company paid to be here, and none can. More on how we choose →
How to hire a roofing contractor in Waukesha
Ask for proof of insurance and a local, physical address. Storm chasers leave town.
Get the manufacturer warranty and the workmanship warranty in writing, separately.
Make sure the quote includes tear-off, decking repairs, underlayment, flashing and disposal.
Never sign over an insurance check or an assignment of benefits before the work is done.
Roofing Contractor questions, answered
How long does a roof replacement take?
Most single-family roofs are replaced in one to three days, depending on size, pitch and material.
Can I put new shingles over old ones?
Some codes allow one overlay, but a full tear-off lets the crew inspect the decking and lasts longer. Most reputable roofers recommend tear-off.
How do I know if hail damaged my roof?
Look for dented gutters, vents and AC fins at ground level. If those show hits, have a roofer inspect the shingles before filing a claim.
On this list? Show it off. 🎖️
Paste this on your website. The badge is free and links back to this page so customers can check for themselves.
<a href="https://homeimprovement.reviews/milwaukee/waukesha/roofing"><img src="https://homeimprovement.reviews/badge/milwaukee/waukesha/roofing/1.svg" alt="#1 Roofing Contractor in Waukesha, WI 2026 - HomeImprovement.Reviews" width="240" height="120"></a>
<a href="https://homeimprovement.reviews/milwaukee/waukesha/roofing"><img src="https://homeimprovement.reviews/badge/milwaukee/waukesha/roofing/2.svg" alt="#2 Roofing Contractor in Waukesha, WI 2026 - HomeImprovement.Reviews" width="240" height="120"></a>
<a href="https://homeimprovement.reviews/milwaukee/waukesha/roofing"><img src="https://homeimprovement.reviews/badge/milwaukee/waukesha/roofing/3.svg" alt="#3 Roofing Contractor in Waukesha, WI 2026 - HomeImprovement.Reviews" width="240" height="120"></a>
<a href="https://homeimprovement.reviews/milwaukee/waukesha/roofing"><img src="https://homeimprovement.reviews/badge/milwaukee/waukesha/roofing/4.svg" alt="#4 Roofing Contractor in Waukesha, WI 2026 - HomeImprovement.Reviews" width="240" height="120"></a>
<a href="https://homeimprovement.reviews/milwaukee/waukesha/roofing"><img src="https://homeimprovement.reviews/badge/milwaukee/waukesha/roofing/5.svg" alt="#5 Roofing Contractor in Waukesha, WI 2026 - HomeImprovement.Reviews" width="240" height="120"></a>
