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 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 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.

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