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TRUSTED BY WINDSOR, WI HOMEOWNERS

  • Average homeowner rating star icon4.6
    Average homeowner rating
  • Verified reviews icon780
    Verified roofing services reviews

Top-Rated Roofers in Windsor - Updated Nov 2026

Avatar for Frey Construction & Home Improvement, LLC
Frey Construction & Home Improvement, LLC
4.6(
209
)
Metal Roofing - Install or ReplaceAsphalt Shingle Roofing - Install or ReplaceAsphalt Shingle Roofing - Install or Replace - For Business+26 more

Serving Windsor, WI and surrounding areas

Approved

Super Service Award Winner

In business since 1995

Free estimates

Emergency services offered

"New roof, gutters and blown in insulation. My house looks great. The whole process was painless. They brought a crew of approximately 8 people. They finished the insulation and roof in one day. The next day for the gutters. Frey Construction was recommended to me and I'm glad I followed that recommendation. I highly recommend Frey Construction."
Additional Photos
Additional Photos
Additional Photos
Additional Photos
Additional Photos

+15

Response time1 day
Response rate100%
4 neighbors recently requested a quote
Avatar for Metal Roofs Direct
Metal Roofs Direct
5.0(
12
)
Metal Roofing - Install or ReplaceMetal Roofing - Install or Replace - For BusinessMetal Roofing - Repair+13 more

Serving Windsor, WI and surrounding areas

Approved (Corporate)

In business since 2010

Free estimates

Warranties offered

"Metal Roofs Direct provided us a 100% custom roof panel profile that we were looking for that no other roofing company could provide. The custom profile we created matched the style and the era of the house. Me being very particular in craftsmanship, Metal Roofs Direct worked closely with me even on a daily basis to make sure I was happy with the installation work quality. Jeremy was the lead that captured and conveyed all my wishes very well. Highly recommend Metal Roofs Direct for their integrity, craftsmanship, and the crew that works extremely hard to satisfy you as the customer. Anthony, as the project manager, worked very hard and made constant adjustments to meet my very high expectation levels. We love our new roof and the amazing experience we had with the entire crew of Metal Roofs Direct. Chad the owner, always did what was right to correct any flaws and was extremely easy to work with."
Door County Roofs
Randolph Church
Door County Roofs
Door County Roofs
Door County Roofs

+16

6 neighbors recently requested a quote
Recommended by85%of homeowners
Avatar for Installers Now, LLC
Installers Now, LLC
4.9(
69
)
Asphalt Shingle Roofing - RepairFlat, Foam or Single Ply Roofing - Repair

Serving Windsor, WI and surrounding areas

Approved

In business since 2010

Free estimates

Emergency services offered

"Sent an email on a Sunday evening and they came out Monday and gave an estimate. Ben and Levi both got on the roof for the inspection. Took pictures, came down (actually went back up to match shingles) and walked me through the issues and then provided an explanation for their estimate. Not pushy and easy to talk to. Listened to my concerns and questions. 2 days later roof was fixed. Provided pictures before, during and after work. Made what was a stressful situation into an easy fix! Already asked for an estimate for another project!"
Hayfield Windows Full Frame Install
Existing Old Windows
Front View
Front and Side View
Front and Side View

+29

Response time11 hrs
Response rate86%
Recommended by100%of homeowners
Avatar for Ridge Top Exteriors, Inc.
Ridge Top Exteriors, Inc.
4.4(
443
)
Asphalt Shingle Roofing - Install or ReplaceAsphalt Shingle Roofing - RepairMetal Roofing - Install or Replace+7 more

Serving Windsor, WI and surrounding areas

Approved (Corporate)

In business since 2002

Free estimates

Warranties offered

"We can?t say enough good things about Ridgetop! We?re very happy with our new roof and gutters. Beau and Joe were excellent with communication leading up to the project, and Drake did a wonderful job as our project manager. We really appreciate everyone?s time, effort, and attention to detail throughout the process. The finished product looks awesome, and we couldn?t be happier with how everything turned out. If you?re looking for a roofing company, we?d highly recommend Ridgetop!"
Before
After
Platinum Premier
30 neighbors recently requested a quote
Recommended by89%of homeowners
Avatar for Sun Vault Roofing LLC
Sun Vault Roofing LLC
5.0(
5
)
Asphalt Shingle Roofing - Install or ReplaceAsphalt Shingle Roofing - RepairFlat, Foam or Single Ply Roofing - Repair+1 more

Serving Windsor, WI and surrounding areas

Approved

In business since 2025

Free estimates

Emergency services offered

Sun Vault Roofing is a locally owned roofing contractor based in Verona, WI, serving Madison and southern Wisconsin. We specialize in residential roof replacement, roof repairs, architectural asphalt shingles, storm damage repairs, and Class 4 impact-resistant roofing. \n \nAs a CertainTeed ShingleMaster, we install premium roofing systems using CertainTeed Landmark, Landmark PRO, and NorthGate ClimateFlex shingles. We believe in honest assessments, transparent pricing, detailed estimates, and recommending repairs when a full roof replacement isn't necessary. \n \nOur Sun Vault One Vault Warranty combines 50-year non-prorated CertainTeed coverage for qualifying manufacturing defects, including labor and tear-off costs, with our exceptional 20-year workmanship warranty and 15 years of transferable protection. \n \n

Oconomowoc Solar
Solar Roof Project
Integrated Solar
Resawn Shake Roof
Finished Roof View

+3

Avatar for Bumble Roofing Of Madison
Bumble Roofing Of Madison
5.0(
9
)
Asphalt Shingle Roofing - Install or Replace

Serving Windsor, WI and surrounding areas

Approved

In business since 2000

Free estimates

Small jobs welcome

Here at Bumble Roofing Of Madison, we are locally owned and operated. No job is too big or too small. Call us today for a free estimate! We are looking forward to going above and beyond on your project soon!

My jobs
Construction
New Roof & Siding
Finished Project
Siding

+1

19 neighbors recently requested a quote
Avatar for Vault Roofing
Vault Roofing
4.4(
70
)
Asphalt Shingle Roofing - Install or Replace

Serving Windsor, WI and surrounding areas

Approved (Corporate)

In business since 1979

Free estimates

Warranties offered

"Ethan spent time working with me to make a 50 year warranted roofing possible and was thorough and great to work with. I would recommend him for your roofing needs."
Roofing
Roofing
Roofing
Roofing
Stunning Curb Appeal

+6

Response time40 mins
Response rate100%
204 neighbors recently requested a quote
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Roofing FAQs, answered by experts

You should hire a roofing professional to install a metal roof, as it’s an essential part of your home and a difficult installation. Your roof provides the most protection for your home among all of the building materials, and any mistakes made during the installation process can quickly lead to roof leaks, water damage, and significant repair costs. A roofing professional will ensure your new roof is installed properly and according to building code to minimize that risk, and they will usually back the installation and materials with a roof warranty for added peace of mind.

Unfortunately, there’s no definitive answer to this question, but the wind rating of your shingles will give you a good idea of what wind speeds can damage your roof. If you’re concerned about damage, inspect your roof following windy conditions to look for signs of wind damage to your shingles. When in doubt, consider hiring a professional who fixes roofs to carry out an expert inspection. Remember that hurricanes, tropical storms, and tornadoes are likely to cause the most damage, but even severe thunderstorms can bring winds that compromise your roofing system.

DIY is not recommended due to safety and expertise requirements. Professional installation ensures proper alignment and sealing.

Roofing estimates vary for many reasons, but the most significant ones include differences in the cost of labor based on the contractor’s experience and overhead costs, as well as the quality of the materials your roofer will use for the job. You should get your estimates itemized and make sure your contractors include details about the materials they plan on using. Doing so allows you to compare not only based on the cost but also the value that you’ll get for your money.

Architectural shingles typically last between 20 and 30 years, though most homeowners should plan on replacing them every 20 to 25 years. While some manufacturers offer warranties for 30 to 50 years, especially for extreme weather, achieving such a long lifespan is rare. The actual lifespan can be shorter in areas prone to strong winds, hailstorms, or other extreme weather. It is recommended to replace your roof before it reaches the end of its life to reduce the risk of roof failure, leaks, and costly property damage. Scheduling regular roof inspections will help you determine your roof's remaining life and identify the best timeline for replacement.

The Windsor, WI homeowners’ guide to roofing services

From average costs to expert advice, get all the answers you need to get your job done.