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TRUSTED BY WINNETKA, IL HOMEOWNERS

  • Average homeowner rating star icon4.6
    Average homeowner rating
  • Verified reviews icon1.1k+
    Verified roofing services reviews

Top-Rated Roofers in Winnetka - Updated Nov 2026

Avatar for Ridgeline Construction Pros Inc
Ridgeline Construction Pros Inc
4.9(
119
)
Asphalt Shingle Roofing - RepairAsphalt Shingle Roofing - Install or ReplaceFlat, Foam or Single Ply Roofing - Repair+7 more

Serving Winnetka, IL and surrounding areas

Approved

In business since 2018

Free estimates

Emergency services offered

"John was the first one to answer my call said he would be happy to come out and look at my roof. I had a small leak that came inside the house. I had someone else come out and tried to see if I was able to get a new roof. Not enough damage. I called John back and he was here when he said he was I'm very happy with what he did to repair the roof. Thank you very much Bruce"
Roof Repair
Roof Repair
Reroof
Reroof
Reroof

+3

12 neighbors recently requested a quote
Recommended by92%of homeowners
Avatar for Bob the Builder Inc
Bob the Builder Inc
4.7(
169
)
Asphalt Shingle Roofing - Install or ReplaceAsphalt Shingle Roofing - Install or Replace - For BusinessAsphalt Shingle Roofing - Repair+8 more

Serving Winnetka, IL and surrounding areas

Approved

In business since 1973

Free estimates

Customers say: Quick response

"It was a pleasure dealing with Wes, Tom and Bob from the estimate all the way through to the clean up. The crew was very pleasant and professional from start to finish. The crew promptly arrived at 7:00 am and were cleaned up by 12:30 pm. The roof on my home has never looked better! Thank You all at Bob The Builder for a great job done at a reasonable price!?"
Additional Photos
Additional Photos
Additional Photos
Additional Photos
Additional Photos

+20

Response time2 days
Response rate100%
7 neighbors recently requested a quote
Avatar for Guardian Roofing Systems, LLC
Guardian Roofing Systems, LLC
4.9(
70
)
Flat, Foam or Single Ply Roofing - RepairFlat, Foam or Single Ply Roofing - Repair- For Business

Serving Winnetka, IL and surrounding areas

Approved

Super Service Award Winner

In business since 2010

Free estimates

Emergency services offered

"Both the owner of Guardian Roofing Systems, LLC, Angelo Ristich and his Lead Repairman Hector were professional and very knowledgeable about the task at hand and what needed to be done. They answered my questions and made sure I had full understanding of the whys of the roof replacement. I was quoted a fair price. The job was completed in a timely manner and true to their word, when the next heavy rain high windstorm happened the new roof held up beautifully. The leaks my house was plagued with aren't a problem anymore. For quality service at a fair price I definitely recommend them."
roof coating
new roof installation
decking
insulation
base sheet

+13

Response time2 days
Response rate91%
79 neighbors recently requested a quote
Avatar for High Tops Roofing & Construction, LLC
High Tops Roofing & Construction, LLC
4.3(
160
)
Asphalt Shingle Roofing - RepairWood Shake or Composite Roofing - RepairFlat, Foam or Single Ply Roofing - Repair+3 more

Serving Winnetka, IL and surrounding areas

Approved

In business since 1996

Free estimates

Emergency services offered

"Dan called yesterday shortly after my initial inquiry. He arrived a little ahead of schedule which was great. He inspected the roof, provided a very reasonable repair estimate, and then completed the work. I would/will recommend High Top Roofing and will use the company to replace the roof completely next spring."
IKO Crown Slate
Hippler Barrington Project
Hippler Barrington Project close
IKO Crown Slate
GAF Timberline Mold Remidiatiomn

+2

Response time5 hrs
Response rate95%
3 neighbors recently requested a quote
Avatar for Enrique Roofing, Corp.
Enrique Roofing, Corp.
4.6(
69
)
Asphalt Shingle Roofing - RepairAsphalt Shingle Roofing - Repair - For BusinessFlat, Foam or Single Ply Roofing - Repair+3 more

Serving Winnetka, IL and surrounding areas

Approved

In business since 2015

Free estimates

Emergency services offered

"Enrique Roofing did a good job replacing my roof. Sergio explained everything what I have to know on how to get the job well done , so the roof will last longer. His prompt coming on time & his people were courteous. Recommended for a job well done !"
Flat roof
Flat roof
Flat roof
New roofing
New roofing

+51

Response time6 hrs
Response rate87%
3 neighbors recently requested a quote
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Roofing FAQs, answered by experts

Flat roofs are a solid option for people who want extra outdoor space. Flat roofs are very common in other parts of the world and only recently has the U.S. started to see the benefit in the increased space. Flat roofs are also easier to maintain and pose much less of a safety risk, which allows for more DIY work for handy homeowners. Some people also build green or living roofs that grow plant life. 

Installing solar panels involves drilling small holes in your roof to secure the solar panel mounting brackets. These brackets hold the solar panels in place and must withstand strong weather conditions so they’re secured into your roof. However, holes and screws are sealed to prevent leaking and further damage.

Many insurance policies will not cover a roof with two layers of shingles. An additional layer of shingles increases the risk of various kinds of damage, and insurers typically won’t pay claims on a roof with an overlay. Adding a layer of shingles may even jeopardize your insurance coverage entirely, so check your policy to ensure you stay within coverage guidelines. 

When it comes to choosing the best roof color for a blue exterior, you have plenty of options. For a classic neutral look, go with a light gray, dark gray, or black roof. Blend gray tones if you want a more eye-catching look for your roof, or go for a different splash of color with a green or even red. Take inspiration from your neighbors if you want your house to fit in on the block.

Asphalt shingles, wooden shakes, and slate or clay roofing tiles are often replaceable without having to replace the entire roof. It's possible to replace just a few shingles or tiles without much trouble in the case of wind damage or other minor problems. DIYers can perform the task in some situations. However, professional repair is always the best bet when it comes to roofing.

The Winnetka, IL homeowners’ guide to roofing services

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