Milwaukee & Waukesha County Contractor | Generations Roofing

Milwaukee & Waukesha County Roofing Contractor

Roofing, siding, windows, gutters, and full interior remodeling — one team, one point of contact, across Milwaukee and Waukesha County. CertainTeed certified. TAMKO authorized. 10 to 30-year warranties. Free estimates, always in writing.

Top rated services
First walkthrough to final cleanup.
Roofing, siding, windows, gutters & interior remodeling — dedicated crews for each service
Storm damage specialists — we photograph, document, and attend the adjuster meeting with you
Written scope, written quote, written warranty — before any deposit is collected
CertainTeed Certified
TAMKO Authorized
10–30 Year Warranties
Licensed & Insured
Free Estimates
Generations Roofing & Remodeling crew truck in Milwaukee
Industry Certifications

Trusted by Wisconsin Homeowners & Businesses

TAMKO Certified Contractor
Roofing Supplier Partner
CertainTeed Certified Contractor
Ply Gem Certified Contractor
Every Service We Offer

What We Do — Complete Scope

We're not a roofing-only company, and we're not a general contractor who dabbles in roofing. Dedicated teams for each category, one point of contact for all of it.

Residential Roofing

Full tear-off and replacement, repair, storm restoration, and insurance claim management. CertainTeed and TAMKO shingle systems with warranties up to 30 years. Most full replacements are done in a single day.

Residential roofing services →
Roof replacement →
Roof repair →

Commercial Roofing

Flat roof inspections, maintenance programs, and full commercial replacements for property managers and building owners. Written inspection reports on every maintenance visit — formatted for CertainTeed warranty compliance.

Commercial roofing services →

Siding & Gutters

Vinyl and fiber cement siding installation and replacement. Seamless gutter systems with custom color matching. Storm-damaged siding documented in the same insurance claim as roofing when both are affected.

Siding installation and replacement →
Gutter installation →

Windows

Replacement windows with proper flashing and sealing for Wisconsin's freeze-thaw climate. Single-window replacements to full-house projects across Wauwatosa, Mequon, Racine, and Kenosha.

Window installation →

Interior Remodeling

Kitchen renovations, bathroom remodels, basement finishing, and home additions. Same project management as exterior work — written scope, clear milestones, and a walkthrough at completion.

Kitchen and bathroom remodeling →

Storm Damage & Insurance Claims

Alexis walks every storm-damaged property personally. He photographs impact patterns, measures hail bruising on soft metals, and prepares the documentation package before the adjuster arrives. He attends the inspection.

Storm damage and insurance claim assistance →
Storm Damage Specialists

Storm Damage & Insurance Claims

This is where a lot of homeowners don't know they need help until they're already in the middle of a dispute with their insurance company. A hailstorm that hits Wauwatosa in June damages roofs, siding, and gutters simultaneously — and the difference between a full insurance-covered replacement and a denied or underpaid claim usually comes down to documentation.

Our Project Consultant walks every storm-damaged property personally. He photographs impact patterns, measures hail bruising on soft metals, and prepares the documentation package before the adjuster shows up.We attend the inspection.

Hasan M.

"They noticed a few key spots on the roof that needed replacement and worked with my insurance company to give me the full replacement quote."

Nasem Thabteh

"Alexis came out, assessed the damage, sent it to our insurance adjuster — took the headache off our end and got us a new roof replacement."

For storm damage claims, contact Alexis Quesada directly:

alexisquesada@generationsrr.com
Storm damaged roof inspection Milwaukee
Customer Reviews

What Our Customers Say

5.0
Google Reviews

"The quality of their work and their attention to detail truly stand out. Lexi and Niko were so easy to work with and incredibly genuine throughout the whole process. They communicated clearly and followed through on every commitment."

HJ
Haley Johnson
Southeast Wisconsin

"The team was timely, cleaned up each day, and the project was completed as expected. Post project check-off was timely and final touches were done immediately. From start to finish, a very professional team."

SW
Susan Wendt
Milwaukee area

"Generations completed a full roof replacement at our house in Milwaukee and we could not be happier. The process was professional, timely, and skilled from the initial consultation to the final clean-up. Lucas and Nicholas were wonderful."

MT
Marie Templeman
Milwaukee, WI

"I had my roofing and siding done with Generations and couldn't be happier. The crew was on time, professional, and delivered awesome attention to detail. I have encouraged anyone doing a project on their home to check them out."

DV
David Villalobos
Waukesha, WI
Recent Projects

Recent Project Gallery

See our completed work across Milwaukee, Waukesha County, and Southeast Wisconsin.

Service Territory

Where We Work in Wisconsin

Milwaukee, Waukesha, and the surrounding counties — if you're in southeastern Wisconsin, we're coming out.

Our service area
Wisconsin service area map — Milwaukee and Waukesha County
Southeast Wisconsin
View All Wisconsin Locations →
Counties we cover
Milwaukee County
Waukesha County
Racine County
Ozaukee County
Washington County
Cities we serve
Milwaukee Wauwatosa West Allis Greenfield Oak Creek Brookfield Waukesha New Berlin Pewaukee Mequon Racine Kenosha Shorewood Whitefish Bay Franklin Cudahy Menomonee Falls Germantown

Not sure if we cover your area? Call 262-202-2481 — we'll tell you directly whether we can help.

Common Questions

A Few Questions We Hear Often

How long does a roof replacement take?
Most residential replacements in the Milwaukee and Waukesha County area take one day. Larger homes, complex rooflines, or jobs with significant decking replacement can run into a second day. We give you a realistic timeline before the job starts — not after.
What does the warranty cover?
Our warranty structure runs from 10 years for standard repairs up to 30 years for full replacements under qualifying CertainTeed and TAMKO product lines. The manufacturer warranty covers the materials. Our labor warranty covers the installation. Both are in writing before any deposit is collected.
Do you handle commercial and residential on the same project?
Yes, and it happens regularly. Commercial buildings with adjacent residential units, mixed-use properties, and investment portfolios often need both residential-grade work and commercial-grade documentation. We adjust the scope and reporting to match what the property actually needs.
How do I get started?
Call (262) 202-2481 Monday through Saturday between 7am and 6pm, or email info@generationsrr.com. Alexis Quesada handles all new inquiries and will either answer your question directly or schedule a free on-site walkthrough. For storm damage projects, reach Alexis directly at alexisquesada@generationsrr.com. See our contact us and request a free estimate page to get started.
Get Started

Nearly a decade of roofs, siding, windows, and remodels across Wauwatosa, Brookfield, West Allis, and most communities in between.

Free estimates. Written quotes. Real team members who answer the phone. Call Monday through Saturday, 7am to 6pm — or fill out the form and we'll be in touch within 2 hours.

2222 N Mayfair Rd, Wauwatosa WI 53226
Mon–Sat 7AM–6PM

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Roofing · Siding · Windows · Remodeling · Southeast Wisconsin