Roof Replacement Contractor Milwaukee WI | Generations R&R
Home Residential Roofing
Milwaukee & Waukesha County

Residential Roofing in Milwaukee & Waukesha County

Full-service residential roofing for Milwaukee County and Waukesha County homeowners — replacement, repair, reroof, storm damage, and inspections. CertainTeed and TAMKO certified. Written quote before any deposit.

CertainTeed Certified
TAMKO Authorized
Free Estimates
Licensed & Insured
(262) 202-2481
By the Numbers
Generations Roofing & Remodeling
Since 2020
Milwaukee-area owned & operated
48 Five-Star Reviews
★ 5.0 rating on Google
CertainTeed & TAMKO
Manufacturer-certified installer
Written Quote First
Before any deposit is collected
What We Do

Roofing Services for Milwaukee & Waukesha County Homes

Whether you need a full replacement after a storm, a repair on a specific section, an inspection before buying a home, or a reroof to add a second layer — we handle every residential roofing scope in-house with the same crew and the same written quote process. No subcontractors. No surprises after work starts.

Roof replacement Milwaukee Wisconsin
Roof Replacement

Full tear-off and replacement for Milwaukee and Waukesha County homes. CertainTeed and TAMKO architectural shingles, standing seam metal, cedar shake, flat systems. Deck condition assessed before any scope is finalized. Written quote before any deposit.

Full replacement details
Roof inspection Milwaukee Wisconsin
Roof Inspection

On-roof inspection — not a driveway assessment. We document shingle condition, granule loss, flashing integrity, penetration seals, ventilation, and deck condition where visible. Written report provided. Free with any replacement estimate.

Inspection details
Storm damage roof repair Milwaukee
Storm Damage & Insurance Claims

Free inspection after any hail or wind event. We document every affected surface in a single visit, produce a written report in a format insurance carriers expect, and attend the adjuster inspection when that helps the claim. Most storm customers pay only their deductible.

Storm damage process
Reroof Milwaukee Wisconsin
Reroof — Layer Over Existing

Installing new shingles over a single existing layer — permitted in Wisconsin when the deck is sound and local code allows. Lower upfront cost than full tear-off. Not appropriate for every home; deck condition and shingle count assessed before recommending this scope.

Reroof details
Attic insulation Milwaukee Wisconsin
Attic Insulation

Attic insulation assessed and installed alongside roofing projects. Wisconsin's Climate Zone 6 requires R-49 to R-60 for optimal performance. Inadequate insulation is the most common cause of premature shingle failure and ice dam formation — addressed during the roofing estimate at no additional cost.

Insulation services
Manufacturer Partnerships

Certified by the Brands Behind Your Warranty

Our certifications through CertainTeed and TAMKO mean installations qualify for manufacturer warranty programs that uncertified installers can't offer. Ply Gem rounds out our siding product lineup. Written warranty documentation provided at project completion on every job.

CertainTeed

Landmark and Presidential Shake series installation. SureStart Plus warranty programs available through certified installers only. Class 4 impact-resistant shingles for high-hail-frequency zones across southeastern Wisconsin.

Certified Installer
TAMKO

Heritage series architectural shingles — comparable quality to CertainTeed at the standard tier. Extended warranty coverage available through authorized installers. A strong value choice for Milwaukee and Waukesha County residential replacements.

Authorized Installer
Ply Gem

Variform vinyl siding by Ply Gem installed for exterior siding projects. Clean, consistent finish that modernizes curb appeal without high-maintenance exterior requirements. Full-house replacements and trim package matching.

Authorized Dealer
CertainTeed roofing shingles — Saint-Gobain
Recent Work

Recent Roofing Projects — Milwaukee & Waukesha County

A sample of completed roofing projects across our service area. Every project on this page started with a free inspection, received a written quote before any deposit, and was completed by our own crew.

Roof replacement Wauwatosa Wisconsin
Wauwatosa, WI
Full Roof Replacement — CertainTeed Landmark Architectural
Roof and siding New Berlin Wisconsin
New Berlin, WI
Storm Damage — Full Roof & Siding Insurance Claim
Slate tile roof install Wisconsin
Mequon, WI
Premium Slate Tile Installation — Historic Home Restoration
Customer Reviews

48 Five-Star Reviews on Google

5.0
48 reviews · Google

Generations Roofing & Remodeling holds a perfect 5.0 rating across 48 Google reviews. Every review is from a real customer — Milwaukee County, Waukesha County, and the surrounding region.

H
Haley Johnson
Milwaukee County

"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. Would recommend to anyone looking for a contractor who actually does what they say."

Google Review
B
Brian H.
Waukesha County · Multiple Projects

"Zachary is a great owner and truly cares about customer service, which is a refreshing thing these days. I've used them on multiple projects and every time the work is done right, on time, and exactly as quoted. Will be using them again without hesitation."

Google Review
J
Jerad Wagner
Milwaukee County · Investment Property

"Whether you are an investor or working on your primary residence, they can suit all of your needs. Highly professional from start to finish. Project was completed on time, on budget, and cleaned up better than most contractors leave a site."

Google Review
Service Area

Roofing Contractor Serving All of Southeastern Wisconsin

We serve Milwaukee County, Waukesha County, and the surrounding region — no additional travel charge within our primary service area. Click any city below for location-specific roofing information.

Generations Roofing & Remodeling service area — southeastern Wisconsin
Common Questions

Frequently Asked Questions

How much does a roof replacement cost in Milwaukee?
Most residential roof replacements in Milwaukee and Waukesha County run between $8,000 and $18,000 depending on roof size, slope, material choice, and deck condition. Architectural asphalt shingles from CertainTeed or TAMKO are the most common and cost-effective option. We provide a written itemized quote before any deposit is collected — no verbal estimates, no surprises after work starts.
How long does a roof last in Wisconsin?
Architectural asphalt shingles typically last 18 to 25 years in Wisconsin's Climate Zone 6 when properly installed with adequate attic ventilation. Shorter lifespans are almost always tied to ventilation problems from the original installation rather than shingle quality — we assess attic ventilation during every roofing estimate and discuss what it means for the system being installed.
Does homeowner's insurance cover roof replacement in Wisconsin?
Insurance typically covers sudden damage from hail, wind, or falling objects — not wear and gradual deterioration. After a hail or wind event, we provide a free inspection, document all affected surfaces, and attend the adjuster inspection when that helps the claim. Most storm customers pay only their deductible. We do not "work around" deductibles or make representations about what an insurance carrier will approve.
Do you offer free roofing estimates in Milwaukee and Waukesha County?
Yes. Every estimate is free, includes an on-roof inspection, and produces a written itemized quote before any deposit is requested. Alexis Quesada handles all scheduling — she responds same day before 4pm or next morning. We serve all of Milwaukee County and Waukesha County with no additional travel charge within our service area. Call (262) 202-2481 or email alexisquesada@generationsrr.com.
Free Roofing Estimate

Free estimate. Written quote. No deposit until you decide.

Milwaukee County and Waukesha County. Alexis Quesada handles all scheduling — same-day response before 4pm, next morning otherwise.

Get a Free Roofing Estimate

Milwaukee & Waukesha County · Alexis responds personally

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Roofing · Siding · Windows · Remodeling · Southeast Wisconsin