Roofing Company in Sun Prairie, Wisconsin

Your Local Experts in Roofing, Siding, Windows, & Gutters

Residential Roof Replacement for Sun Prairie Homeowners

Sun Prairie has grown fast, and the mix of older homes and newer builds shows up in the way roofs wear. Some hold up well for years, others start showing issues earlier depending on how they were put together and what they’ve been through. Between winter buildup, spring moisture, and summer storms, it adds up. At Oliwill Construction, we step in to figure out what’s actually going on. We inspect the roof, identify problem areas, and determine whether it makes sense to repair sections or move forward with a full replacement.

      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 Work with Oliwill for Your Roofing Project?

Experience Working in Sun Prairie: We’ve handled projects across the area and understand how local conditions and home styles affect how roofs age and perform.
Clear Expectations from the Start: You’ll always be informed on what’s being done, how long it should take, and what it costs before work begins.
Licensed and Covered: Work is completed in line with local requirements, with the right coverage in place throughout the project.
Material Choices That Fit the Area: We guide you toward materials that can handle wind exposure, snow, and seasonal shifts common here.
Projects That Keep Moving: Work is scheduled with intent; our crews show up ready, the job is set up properly, and it moves at a steady pace from start to finish.
Exterior Work Handled Together: Siding, gutters, and windows are among our other services and can be completed during the same project if needed.

Roof Installation Services We Offer in Sun Prairie

Roofing for New Builds and Additions

Roofing on new construction or additions has to be done in the right order, with everything in place before the rest of the exterior is closed in. We install the full system from the base up, making sure airflow, layering, and material placement are handled correctly from the start.

Full Roof Replacement

There’s a point where continuing to patch a roof just leads to more problems. We strip everything down, take a close look at the decking and problem areas, make necessary repairs, and install a new roof that’s made to handle the conditions homes in Sun Prairie deal with each year.

Material Options for Every Need & Budget

Metal Roofing: A durable option that sheds snow well and stands up to wind and impact over time.

Asphalt Shingles: A highly practical choice for most homes, offering solid protection and numerous different styles at a more manageable cost.

Custom & Specialty Roofing: Some roofs don’t follow standard lines. In those cases, we adjust the approach to match the layout instead of forcing a typical setup.

Our Roof Replacement Process

1

Initial Walkthrough: The roof is reviewed up close to understand where it’s wearing down, how previous work has held up, and what condition the underlying structure is in.

2

Written Plan: A full outline of the project is put together covering scope, materials, timing, and cost so everything is defined before work begins.

3

Installation: The existing roof is removed, the decking is checked and repaired where needed, and the new roofing system is installed in stages so each layer is set correctly and tied into the next.

4

Final Check & Cleanup: Once installation is complete, the roof is gone over again and the property is cleared of leftover materials and debris.

5

Closeout: The project is finished only after the work lines up with your plan and everything has been completed as expected.

Is It Time for a Roof Replacement?

Roof issues tend to build gradually. Signs to look out for include:

Shingles that are loose, cracked, or missing
Granules collecting in gutters or near downspouts
Interior staining or signs of moisture
Weakened sections below the shingles
Rooflines that appear uneven or sagged
Recurring repairs tied to storm impact or changing seasons

As these issues show up, having it looked at would be advisable. We offer free estimates to help you understand what comes next.

Kick Off Your Roof Replacement

A proper evaluation is the first step. We’ll take a look at the roof, explain what we’re seeing, and go over realistic options based on its condition.

Contact Us