Roofing Company in Middleton, Wisconsin

Trustworthy Roofing, Siding, Gutter, & Window Services

Residential Roofing for Middleton’s Changing Climate

Middleton sits right in the path of shifting Midwest weather, where one season rolls into the next without much warning. Winters bring heavy snow, spring adds steady moisture, and summer storms hit fast, each one wearing on a roof in different ways over time. The Oliwill Construction team takes those conditions into account when inspecting, planning, and installing roofing systems.

Some roofs are clearly at the end of their run, while some just need a smart plan before problems start. Our approach comes down to what fits the home, its structure, its age, and the conditions it deals with over time.

      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!
  
 
  
  
 
 
     Verified by Trustindex  Trustindex verified badge is the Universal Symbol of Trust. Only the greatest companies can get the verified badge who has a review score above 4.5, based on customer reviews over the past 12 months. Read more

Why Partner with Oliwill for Roofing?

Experience with Local Housing Styles: We’ve worked on many different homes across Middleton and understand how different builds come together, adjusting our approach based on how each roof is structured and ventilated.
Clear & Direct Communication: You’ll get clear explanations, realistic timelines, and detailed estimates, with no vague language or surprises halfway through the job.
Properly Licensed and Insured: All projects are completed with proper coverage and adherence to local requirements.
Materials Chosen for This Climate: We will help you choose materials that hold up through freeze-thaw cycles, wind, and long winters common in Middleton.
Efficient & Well-Managed Projects: Our crews work with purpose; jobs are planned out and carried through at a steady pace from start to finish.
Exterior Work Beyond Roofing: Siding, gutters, and windows work can also be completed alongside the roofing work.

Roof Installation Services We Offer in Middleton

Roofing for New Builds and Additions

New construction and additions need a roof that’s put together correctly from the start. We install everything as a complete setup, layering materials properly, setting up ventilation, and making sure it’s done right before anything gets covered up.

Full Roof Replacement

At a certain point, patching stops making sense. We tear off the old roof, check what’s underneath, fix anything that shouldn’t be left as-is, and install a new roof that can handle the weather here without constant issues.

Material Options for Every Need & Budget

Metal Roofing: A solid option for homeowners thinking long-term. Metal roofs shed snow efficiently and hold up very well against wind and impact. Asphalt Shingles: A widely used choice that balances cost and reliability. Modern shingle systems offer good protection and come in a plethora of styles. Custom & Specialty Roofing: Homes with unusual layouts or tricky rooflines need a different approach. We adjust the roofing work around the structure instead of trying to make a standard setup fit.

Our Roof Replacement Process

1

On-Site Assessment: We start by evaluating the current roof, noting any structural concerns and discussing your goals.

2

Detailed Proposal: You will receive a written plan outlining materials, scope, timing, and cost so you know exactly what to expect.

3

Installation Phase: The roofing system is installed according to manufacturer specifications and local code, with a focus on longevity and resistance to the elements.

4

Final Inspection & Cleanup: After installation, we will walk the property, check the finished work, and leave the site clean and ready to use.

5

Project Completion: The job isn’t wrapped up until everything meets both our standards and yours.

Signs it’s Time for a New Roof

Roofs almost never fail all at once; most show warning signs along the way. You may need a replacement if you’re noticing:

Shingles that are breaking down, lifting, or missing
Excess granules collecting in gutters
Water marks or moisture issues inside the home
Soft or weakened areas beneath the surface
Uneven rooflines or visible sagging
Ongoing repairs after storms or seasonal damage

When these issues start to show, or if your roof is simply getting older, it’s worth having it evaluated. Oliwill Construction offers free estimates to help you plan your next steps.

Get Started on Your Roof Replacement

Your roof may be ready for an upgrade, or it might just need a closer look. We’ll assess the condition and walk you through your options with no pressure.

Call Us

or request your free estimate online.