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TRUSTED BY JACKSON, WI HOMEOWNERS

  • Average homeowner rating star icon4.5
    Average homeowner rating
  • Verified reviews icon513
    Verified roofing services reviews

Top-Rated Roofers in Jackson - Updated Nov 2026

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 Jackson, WI and surrounding areas

Approved (Corporate)

In business since 2010

Free estimates

Warranties offered

"Chad and his crew were absolutely amazing. From the first sales call, until the last nail of completion, I knew we could count on him. He had been referred, and we immediately felt comfortable with Chad, as he patiently explained the value in a significant undertaking - this roof will be there another 200 years, the quality is just that good! The work was on-time, professional, and the crew did a great job of cleaning up when they are done. We plan to use Metal Roofs Direct for other roofs when the time comes!"
Door County Roofs
Randolph Church
Door County Roofs
Door County Roofs
Door County Roofs

+16

8 neighbors recently requested a quote
Recommended by85%of homeowners
Avatar for Midwest Home Exteriors
Midwest Home Exteriors
4.6(
11
)
Natural Slate Roofing - Install or ReplaceAsphalt Shingle Roofing - Install or ReplaceAsphalt Shingle Roofing - Install or Replace - For Business+15 more

Serving Jackson, WI and surrounding areas

Approved

In business since 2009

Free estimates

Emergency services offered

"I had a great experience with Midwest Home Exteriors from start to finish! The owner, James, and the office staff were incredibly easy to work with during the entire process of getting a new roof and gutters. They worked closely with my insurance agent, the crews and I to make this process run very smoothly. The whole process was fast and hassle-free, and the finished roof and gutters look incredible. I highly recommend them to anyone needing quality work done on their home!"
Oak Creek, Wisconsin – Siding & Roof
Updated!
Oak Creek, Wisconsin – Roof Updated!
Greendale, Wisconsin – Roof Updated!
Oak Creek, Wisconsin – Roof Updated!
Franklin, Wisconsin – Roof Updated!

+11

Response time1 day
41 neighbors recently requested a quote
Recommended by81%of homeowners
Avatar for Weather Pro Exteriors Inc.
Weather Pro Exteriors Inc.
4.1(
33
)
Asphalt Shingle Roofing - Install or ReplaceAsphalt Shingle Roofing - RepairMetal Roofing - Install or Replace+26 more

Serving Jackson, WI and surrounding areas

Approved

In business since 2008

Free estimates

Warranties offered

"We had a roof that needed cap shingle replacement prior to the sale of the home due to degradation of the previous shingles of the wrong type. Weather Pro Exteriors had someone out quickly to provide an estimate and they were able to schedule the repair within a week. The customer service was excellent and they were easy to work with. Pricing was significantly lower than another quote I received and we are happy with the work performed. Very personable and responsive!"
Additional Photos
Additional Photos
Unlike other companies in town, we use our own in-house roofing crews to install your roof. Ensuring you get the best install with he best warranties every time.
James Hardie Siding Replacement
Additional Photos

+3

Response time1 day
Response rate100%
19 neighbors recently requested a quote
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Roofing FAQs, answered by experts

Costs vary by repair scope, materials needed, and labor, with average repairs ranging from $300 to $1,000, contingent on roof size.

The average cost to winterize a house is about $250, but it can range from $65 to $1,000 depending on the type of work that needs to be done. For homeowners that are experienced DIYers, it can save quite a bit on costs. However, you shouldn’t attempt tasks you aren’t familiar with or are potentially dangerous.

The best way to prevent wind damage to your roof, especially if you live in an area prone to hurricanes, tropical storms, or tornadoes, is to invest in a roofing product with high wind resistance. Look for the ASTM D3161 and ASTM D7158 ratings to see the specific wind speeds your roofing product can withstand. Impact-resistant shingles have the highest wind resistance ratings and will give you the best chance of avoiding wind damage.

Whether you should choose a flat roof or a sloped roof depends on your particular situation. Flat roofs tend to be less expensive to install. However, sloped roofs have longer lifespans and stand up better to heavy snow and other inclement weather.

Keep in mind that even a flat roof needs to have a slight slope, usually around 1/2 inch for every foot. If it is completely flat, water will pool and cause damage, either from weight or leakage or rot.

The best type of roof vent depends on the size, type, and construction of your roof as well as the environmental conditions in and around your home. In many cases, an active ventilation system that draws in fresh air and exhausts air out through the attic is the most effective. Active ventilation systems include roof ridge vents with baffles, turbine vents, and soffit vents that are used together with another type of vent.

The Jackson, WI homeowners’ guide to roofing services

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