Roofing Company in Cottage Grove, Wisconsin

Your Local Roofing, Siding, Gutter & Window Specialists

Residential Roofing Made for Midwest Weather

Cottage Grove homes see their fair share of wear and tear, from long and brutal winters to sudden summer storms and very harsh humidity. The Oliwill Construction team helps homeowners stay ahead of it with roofing work that’s done right the first time. We use the best materials for the job, take the time to install them properly, and are always clear with homeowners about what’s being done and why.

      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 Choose Oliwill Construction as Your Roofing Partner

Familiar with Local Conditions: Working in Cottage Grove and across south central Wisconsin provides familiarity with what roofs here experience, from heavy snow to wind-driven rain, and building with that in mind.
More Than Just Roofing: In addition to roof work, we handle siding, gutters, and windows; our team can take care of your exterior projects as well.
Experience With All Types of Homes: We work on everything from single-family houses and garages to duplexes and multi-unit properties, adapting our approach based on the structure.
Properly Licensed and Insured: Oliwill Construction is fully licensed and insured, so homeowners are certain the work is being handled responsibly and professionally.
Material Choices That Make Sense: Materials are chosen based on how they perform and last in Wisconsin weather, with options such as asphalt shingles or metal roofing.
A Reputation Earned Locally: Much of our work comes from referrals and repeat customers throughout Dane County, built on jobs finished on time and with quality craftsmanship.

Roof Installation Services We Offer in Cottage Grove

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

New Roof Installation

When a home or building is starting from scratch, we handle the entire roofing process, coordinating installation so the finished roof meets local code and is ready for Wisconsin weather from day one.

Full Roof Replacement

Older roofs eventually reach a point where repairs stop making sense. When shingles fail, leaks appear, or storms take their toll, we tear off the existing roof, address any underlying issues, and install a new system made to perform in the long-term.

Material Options for Every Need & Budget

Metal Roofing

A strong option for homeowners who want something for the long haul. It performs well against hail, high winds, and heavy snow, and assists with temperature control inside the home.

Asphalt Shingles

Often used on residential homes, asphalt shingles provide consistent protection and keep installation and replacement costs lower than many alternatives.

Custom & Specialty Roofs

For roofs with steeper pitches, uncommon designs, or specific structural needs, we design and install roofing systems that match the structure and the way the building is used.

Our Roof Installation Process

Initial Visit and Estimate: The process starts with an on-site look at your roof, where we check existing conditions, talk through concerns, and give an estimate based on the work that actually needs to be done.
Clear Scope Before Work Begins: Before anything moves forward, you will receive a written outline covering materials, labor, schedule, and cost.
Installation: Once scheduled, the roof is installed according to local code and manufacturer requirements, with attention paid to how it will handle wind, snow, and rain.
Site Cleanup and Walkthrough: After the work is finished, the area will be cleaned and the roof inspected to make sure everything was completed correctly.
Standing Behind the Work: We don’t consider a job finished until the work meets our standards and the homeowner is satisfied with the result.

Is Your Roof Due for Replacement?

It may be time to think about a replacement if you’re seeing issues like:

Shingles that are lifting, breaking down, or missing altogether
Excessive grit collecting in gutters or bare spots on shingle surfaces
Water marks, damp areas, or leaks inside the house
Roof decking that feels soft, looks deteriorated, or shows signs of rot
Sagging sections of the roof or daylight visible from the attic
Ongoing repairs or damage caused by repeated storms, hail, wind, or ice

If your roof is showing any of these signs, or if it’s simply reaching the end of its lifespan, Oliwill Construction can take a look and provide a free inspection and estimate with no obligation.

Start Your Roofing Project Today

Have any questions or want to receive a free estimate for your roofing project? Reach out today to learn more about our replacement and installation options.

Contact Us