Roofing Company in Deerfield, Wisconsin

Roofing, Siding, Gutter & Window Specialists in WI

Residential Roofing for Wisconsin Homeowners

Homes in Deerfield span decades of construction, and the way a roof wears tells a different story on every structure. Older homes reveal issues slowly through softened decking or persistent leaks; newer builds show stress after heavy snow loads or fast-moving summer storms. With Wisconsin’s freeze-thaw cycles, spring moisture, and high winds in play, roofing systems here have to be planned. Oliwill Construction works with Deerfield homeowners on roof installations and replacements that respond to the home’s condition, its design, and the real demands of the climate it sits in.

      EXCELLENT  
   Based on 234 reviews 
    
 
 
 
   
 
 
       Posted on Google  
   
   Greg Hyer 
 
 
 
 Trustindex verifies that the original source of the review is Google. Terrific quality work — competitive price — thorough clean-up — great team — highly recommend
  
 
      Posted on Google  
   
   Elissa Zollin 
 
 
 
 Trustindex verifies that the original source of the review is Google. Our siding looks great.  I appreciate the guidance Oliver gave us on what products would work best for us.
  
 
      Posted on Google  
   
   Scott Coleman 
 
 
 
 Trustindex verifies that the original source of the review is Google. Oliver and William were very friendly and professional and their team did great work! Very happy with our roof and siding and window wraps. I would recommend them to anyone looking to fix up their house. This is the second time they've fixed up our house in 2 years (thanks hail!) And both times they've done excellent work.
  
 
      Posted on Google  
   
   Mai Seng Thao 
 
 
 
 Trustindex verifies that the original source of the review is Google. We highly recommend Oliwill Construction if you are in need of a roof replacement. Oliver and his team provide reliable and fast communication throughout the process. The team ensures you have a good understanding about the work being done each step of the way. We also appreciated that the materials were brought on site the same day the work was getting done compared to our neighbors who had materials sitting on their lawn for days or weeks prior to the scheduled work date. If you’re looking for a positive roof replacement experience we recommend contacting Oliwill Construction!
  
 
      Posted on Google  
   
   Raymond Young 
 
 
 
 Trustindex verifies that the original source of the review is Google. Did great job finished in one day, I recommend to anyone for their roof
  
 
      Posted on Google  
   
   German Cortes 
 
 
 
 Trustindex verifies that the original source of the review is Google. We had a fantastic experience with Oliwill Construction. From the initial consultation to the completion of our roof replacement and leaf guards, their team demonstrated top-tier professionalism and quality workmanship. We are extremely satisfied and strongly recommend them.
  
 
      Posted on Google  
   
   Carey Karabis 
 
 
 
 Trustindex verifies that the original source of the review is Google. We were totally pleased with the entire job that was done for us .
  
 
      Posted on Google  
   
   Mike Pahmeier 
 
 
 
 Trustindex verifies that the original source of the review is Google. Oliwill did our roof recently and it was a smooth job, start to finish. Their guys finished in a day even with a rain delay. The cleanup was thorough and by sundown everything looked just like it looked that morning. Except the roof of course, that looked 100% better. Definitely recommend Oliwill!
  
 
      Posted on Google  
   
   Karime Grajales-Patton 
 
 
 
 Trustindex verifies that the original source of the review is Google. Since the first appointment with their team, our perception was of trust, professionalism, honesty and, they delivered. The time and scope was as it was agreed and they had helped us to navigate not only the technical-construction process, changes and currently, the closing process with the insurance. We had the opportunity to be in constant communication with Oliver but also with other team members from Oliwill and each of them, was open to solve our questions and concerns.
  
 
      Posted on Google  
   
   AJ Blimling 
 
 
 
 Trustindex verifies that the original source of the review is Google. Great and fast workers. Very professional
  
 
  
  
 
 
    Verified by Trustindex  Trustindex verified that these reviews were published on Oliwill Construction's Google Business Profile. Learn more

Why Choose Us as Your Roofing Company

Familiarity with Local Roofs: We understand how Deerfield homes are put together, from older framing styles to newer construction, and we adjust our roofing approach based on roof pitch, structure, and age.
Residential Experience Across Property Types: Our work includes single-family homes, garages, duplexes, and smaller multi-unit buildings, with each project planned around the structure and roof layout.
Licensed and Insured Work: We’re fully licensed and insured, which means your home, your property, and the work itself are protected throughout the entire project.
Materials Selected for Long-Term Use: Material choices are based on how they hold up in Wisconsin conditions over time, including snow, wind, and moisture exposure.
Exterior Services Beyond Roofing: In addition to roofing, we also handle siding, gutters, and windows, so homeowners can address exterior projects with one company.
A Strong Local Track Record: Many Deerfield projects come from referrals and repeat customers who value consistent work and communication from start to finish.

Roof Installation Services We Offer in Deerfield

At Oliwill, we provide a full suite of services to meet your roofing needs:

Roof Installation for New Construction

For new homes and additions, we install complete roofing systems that meet local building requirements and are suited for long-term use in Wisconsin conditions.

Roof Replacement

When an existing roof shows widespread wear, storm damage, or age-related issues, we remove the old materials, inspect the underlying structure, and install a new roofing system built to last.

Material Options for Every Need & Budget

Metal Roofing

Metal roofing is often selected for its durability and resistance to snow, wind, and hail; it is a good fit for homeowners planning long-term.

Asphalt Shingles Roofing

Commonly used on residential homes, this roofing type provides reliable coverage and keeps installation and replacement costs more manageable.

Custom & Specialty Roofing

Steep rooflines, uncommon designs, or non-standard structures require a tailored approach, with systems planned around the building itself.

Our Roof Installation Process

Property Evaluation: The process begins with an on-site review of the roof to assess current conditions and discuss any concerns.
Written Estimate and Scope: Homeowners receive a written outline of the work, materials, schedule, and pricing before any work begins.
Roof Installation or Replacement: Work is completed according to local code and manufacturer requirements, with attention to weather exposure and roof structure.
Final Review and Cleanup: Once the project is complete, the site is cleaned and the roof is checked to confirm the work was done correctly.
Standing Behind the Work: We consider a project complete only after the work meets our standards and homeowner expectations.

Does Your Home Need a Roof Upgrade?

It may be time to look into a replacement if you notice:

Shingles lifting, cracking, or missing
Granules collecting in gutters or visible wear
Interior water stains or active leaks
Soft, damaged, or rotting roof decking
Sagging roof areas or light visible from the attic
Repeated storm damage or frequent repairs

If any of these apply, or if your roof is visibly nearing the end of its lifespan, Oliwill Construction can provide a free estimate for a roof replacement.

Start a Roofing Project With Us

If you have questions or would like to schedule an inspection, contact Oliwill Construction to discuss your roofing needs.

Get in Touch