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 219 reviews 
    
 
 
 
   
 
 
       Posted on Google  
   
   Amy Ramesh 
 
 
 
 Trustindex verifies that the original source of the review is Google. Fantastic, helpful, easy to contact, answered all questions, great completed work. By far the best experience I've had with fixing my 98 year old home in the 23 years I've owned it
  
 
      Posted on Google  
   
   Duane Hansen 
 
 
 
 Trustindex verifies that the original source of the review is Google. I chose Oliwill to replace my roof (storm damage) as their cost matched my insurance payment. They did a nice job. Quality material and did adequate clean up after. A couple shingles didn’t appear adequately flat and once alerted, they came back and took care of that final detail.
  
 
      Posted on Google  
   
   Brian 
 
 
 
 Trustindex verifies that the original source of the review is Google. I'm not good at writing reviews so I will keep it simple... All I can say is I'm very glad I chose OliWill Construction to replace my roof. The reason I chose OliWill is the level of professionalism and knowledge during and after his inspection outperformed the other contractors. On the day of replacement they were on-time and worked all day until it was finished.  The crew were also very respectful of my property and cleaned up extremely well after they completed the work. I highly recommend OliWill Construction and will use their services again for future home projects.
  
 
      Posted on Google  
   
   Heidi Olsen 
 
 
 
 Trustindex verifies that the original source of the review is Google. I’m extremely pleased with my gutter installation. The team communicated clearly from start to finish, which made the whole process feel smooth and stress‑free. They took the time to listen to my concerns and made sure every detail was handled the way I wanted. The workmanship is excellent — the gutters look clean, well‑fitted, and built to last. They were respectful of my property and didn’t try to upsell anything unnecessary. Overall, the combination of great communication, quality work, and genuine attentiveness made this a standout experience. I’d confidently recommend them.
  
 
      Posted on Google  
   
   Lisa 
 
 
 
 Trustindex verifies that the original source of the review is Google. I had hail damage on my house and garage roof, gutter guards and some siding.  Oliver was quick with an estimate for replacement  and scheduling time was reasonable as well. He had great communication along the way and is quick to text. The crew was wonderful and not a single plant was trampled. They were all friendly, efficient and clean up was amazing. I’m very happy with the whole experience and would highly recommend.
  
 
      Posted on Google  
   
   Mike Grupe 
 
 
 
 Trustindex verifies that the original source of the review is Google. I was very pleased with every aspect of the job. Oliver, who originally gave us an estimate, was friendly and professional. William, who came to the house before the work was done, was also helpful and a pleasure to talk to. I had a good experience with the people who did the work. They were efficient and cleaned up well after the work was done. I also had a good experience working with Karina, who works in the office. She promptly answered my questions and sent documents and information. I would definitely work with Oliwill Construction again.
  
 
      Posted on Google  
   
   Devin Martin 
 
 
 
 Trustindex verifies that the original source of the review is Google. Storm damage can be hectic and stressful. Oliwill came through with a quote for a new roof and gutters that was better than the out-of-town storm chasers, keeping our money in our community.
  
 
      Posted on Google  
   
   Kathleen Sloniker 
 
 
 
 Trustindex verifies that the original source of the review is Google. After recent storms had left 3 holes in our roof, Oliwill patched the holes that same day, so we did not sustain any more damage to the house with the predicted rain. Within a couple of weeks they replaced the roof, soffits, and gutter guards. Everything looks great and was done so quickly! I would highly recommend Oliwill for your roofing needs!
  
 
  
  
 
 
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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