Waukesha County, WisconsinWaukesha Home Exterior Guide

Contractor research

Roofing and siding contractors serving Waukesha County

A starting list of companies that publicly document exterior work in this county, plus the questions that separate a thorough bid from a thin one.

Listing a company here is not an endorsement of that company by this publication, and it does not mean the company endorses this publication or BOLD Brothers Roofing & Exteriors. The entries are not ranked. They are alphabetical, and each field is filled in only where the company’s own website confirmed it on the date shown.

For the full explanation of how these companies were selected, what was checked, and what could not be confirmed, read the full roofing company comparison guide. For siding-specific vetting, see how to compare siding contractors.

Comparison at a glance (alphabetical, unranked)

Every entry below is drawn from the company’s own website on the date shown. Where a detail was not stated on the pages reviewed, it reads “Not confirmed” rather than a guess.

BOLD Brothers Roofing & Exteriors

Verified service area
Waukesha County and nearby southeastern Wisconsin communities, worked from a Butler, Wisconsin base at the eastern edge of the county
Roofing
Full roof replacement and tear-off, roof repair and leak investigation, storm damage assessment and documentation, decking replacement, ventilation review
Siding
Full siding replacement including removal, weather barrier, flashing, trim, soffit and fascia work as part of a whole-exterior scope

Four Leaf Roofing & Windows

Verified service area
Company website states crews cover 17 cities across six southeastern Wisconsin counties including Waukesha, and names New Berlin, Waukesha, Brookfield and Milwaukee
Roofing
Residential and commercial roofing, roof repair and replacement, TPO and rubber roofing, seamless gutters
Siding
Siding installation, repair and replacement in vinyl, James Hardie fibre cement, LP SmartSide engineered wood and natural cedar

Generations Roofing & Remodeling

Verified service area
Milwaukee and Waukesha County, per the company website.
Roofing
Residential roof replacement, repair and storm restoration; the site lists CertainTeed and TAMKO systems.
Siding
Vinyl and fiber cement siding, seamless gutters and replacement windows, per the company website.

Heins Contracting

Verified service area
Waukesha, Wisconsin and surrounding areas, per the company's Waukesha service page.
Roofing
Asphalt and shake roofing, metal roofing, flat roofing, roof coatings, storm damage and ice dam services.
Siding
Not confirmed on the pages reviewed.

Integrity Roofing

Verified service area
All of Waukesha County, including Brookfield, Butler, Delafield, Menomonee Falls, New Berlin, Pewaukee, Sussex and Waukesha, per the company's Waukesha County page.
Roofing
Roof replacement and roof repair for Waukesha County and southeastern Wisconsin.
Siding
LP siding work is named on the company's Waukesha County page.

Paragon Exteriors

Verified service area
Waukesha and Milwaukee counties and other southeastern Wisconsin counties, per the company website.
Roofing
Asphalt and architectural shingle roof replacement for homes, townhomes and condos.
Siding
Not confirmed on the pages reviewed.

Reimer Roofing & Remodeling

Verified service area
Brookfield, Delafield, Elm Grove, Hartland, Muskego, New Berlin, North Prairie, Pewaukee, Waukesha and other surrounding communities, per the company website.
Roofing
Roof installation, tear-off, re-roofing, new construction roofing, soffit and fascia repair and replacement.
Siding
Siding is listed among the company's services alongside windows and remodeling.

Ridge Top Exteriors

Verified service area
Company website names Milwaukee and surrounding areas including Waukesha, West Allis and Brookfield, and publishes a Waukesha roofing page
Roofing
Asphalt shingle roofing installation and roof repair; storm damage repair; commercial roofing
Siding
Siding installation in vinyl, LP SmartSide and James Hardie

Robidoux Brothers, LLC

Verified service area
Waukesha, Milwaukee and Kenosha areas of southeast Wisconsin, per the company website.
Roofing
Roofing, seamless gutters, skylights and related exterior construction.
Siding
Siding, windows and exterior trim are listed on the company website.

WeatherPro Exteriors

Verified service area
Southeastern Wisconsin including Waukesha; company publishes a dedicated Waukesha, WI service page
Roofing
Residential and commercial roofing, roof replacement and roof repair; asphalt shingle and metal roofing systems
Siding
Siding, plus windows, doors, gutters and attic insulation

Open directory: 48 roofing and siding contractors

These companies are listed, not featured. They are in alphabetical order, with no ranking, no rating and no recommendation attached to any entry. A website or phone number appears only where the company or a public business listing published it. Where nothing was publicly listed, the field reads “Not listed” rather than a guess. Checked September 16, 2026.

Company details change. Confirm licensing, insurance and current contact information with the company directly before you sign anything.

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