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Asphalt shingle roofing installers and replacers in Winnetka

Avatar for Tri-Star Roofing and Construction
Tri-Star Roofing and Construction
1229 North Monticello Ave.
4.50(
2
)
Approved Pro
Tri-Star Roofing and Construction
1229 North Monticello Ave.
4.50(
2
)
Approved Pro
Customers say: Quick response
Recommended by 100% of Angi customers
Recommended by 100% of HomeAdvisor customers
29 years of experience

Tri-Star Roofing and Construction, is committed to excellence in every aspect of our business. We uphold a standard of integrity bound by fairness, honesty, and personal responsibility. Our distinction is the quality of service we bring to our customers. Accurate knowledge of our trade combined with ability is what makes us true professionals. Above all, we are watchful of our customers interests, and make their concerns the basis of our business.

"n/a"

Curt B on April 2022

Tri-Star Roofing and Construction, is committed to excellence in every aspect of our business. We uphold a standard of integrity bound by fairness, honesty, and personal responsibility. Our distinction is the quality of service we bring to our customers. Accurate knowledge of our trade combined with ability is what makes us true professionals. Above all, we are watchful of our customers interests, and make their concerns the basis of our business.

"n/a"

Curt B on April 2022


Avatar for L.E.N. Construction, Inc.
L.E.N. Construction, Inc.
1900 Techny Court
4.81(
38
)
Approved Pro
L.E.N. Construction, Inc.
1900 Techny Court
4.81(
38
)
Approved Pro
Customers say: Quick response
Recommended by 97% of Angi customers
Recommended by 97% of HomeAdvisor customers
26 years of experience

Len Roofing & Remodeling - We show up on time and nail it - Meticulous clean-up and respect for your property - Speed meets artistry for your complete satisfaction - We specialize in roofing, siding, windows, gutters, sheet metal & tuck-pointing. Our mission is to be acknowledged as the #1 Home Improvement Company in Chicago and the suburbs. We believe in offering a wide variety of products and educating our customers on solutions to best fit their needs. We recognize that open communication throughout the installation process is critical to our customer satisfaction. We certify our craftsmanship with the strictest quality control guidelines and personally monitor each job from start through completion.

"Fast and professional. The damage was more extensive than originally thought. L.E.N. documented everything for the insurance company and worked with me for what wasn't covered to keep my costs down."

Davis G on July 2020

Len Roofing & Remodeling - We show up on time and nail it - Meticulous clean-up and respect for your property - Speed meets artistry for your complete satisfaction - We specialize in roofing, siding, windows, gutters, sheet metal & tuck-pointing. Our mission is to be acknowledged as the #1 Home Improvement Company in Chicago and the suburbs. We believe in offering a wide variety of products and educating our customers on solutions to best fit their needs. We recognize that open communication throughout the installation process is critical to our customer satisfaction. We certify our craftsmanship with the strictest quality control guidelines and personally monitor each job from start through completion.

"Fast and professional. The damage was more extensive than originally thought. L.E.N. documented everything for the insurance company and worked with me for what wasn't covered to keep my costs down."

Davis G on July 2020


Avatar for Power Home Remodeling
Power Home Remodeling
2501 Seaport Drive
4.52(
339
)
Approved Pro
Power Home Remodeling
2501 Seaport Drive
4.52(
339
)
Approved Pro
Customers say: Super punctual
3692 local quotes requested
33 years of experience

Does your home need replacement roofing that is high-quality, energy-efficient, and comes with a lifetime warranty? We're the nation's largest full-service exterior home remodeler and over 1000 lifetime Angi Super Service Awards. We can help transform your house into the beautiful and cost-effective home you've always dreamed of. At Power, you'll love our friendly, knowledgeable, and professional remodeling consultants and be delighted by our top-rated installation process. But don't take it from us. We've served over 1,000,000 customers across the U.S earning a 95% overall satisfaction rating. For a free, no-obligation estimate, call: (610) 990-4243 or visit https://powerhrg.com/project-quote/.

"I've already recommend them to my mom. they are perfect!"

SEOKJOO K on March 2025

Does your home need replacement roofing that is high-quality, energy-efficient, and comes with a lifetime warranty? We're the nation's largest full-service exterior home remodeler and over 1000 lifetime Angi Super Service Awards. We can help transform your house into the beautiful and cost-effective home you've always dreamed of. At Power, you'll love our friendly, knowledgeable, and professional remodeling consultants and be delighted by our top-rated installation process. But don't take it from us. We've served over 1,000,000 customers across the U.S earning a 95% overall satisfaction rating. For a free, no-obligation estimate, call: (610) 990-4243 or visit https://powerhrg.com/project-quote/.

"I've already recommend them to my mom. they are perfect!"

SEOKJOO K on March 2025


Midtown Home Improvements, Inc. (Chicago)*
945 N Edgewood Ave
4.59(
621
)
Approved Pro
Midtown Home Improvements, Inc. (Chicago)*
945 N Edgewood Ave
4.59(
621
)
Approved Pro
Customers say: Quality work
Recommended by 92% of Angi customers
Recommended by 92% of HomeAdvisor customers
33 years of experience

Midtown Home Improvements is your neighborhood home improvement specialist. Whether you are looking for energy savings with Triple Pane Windows, a new low maintenance PVC Cellular deck, a maintenance free vinyl fence, or the thickest permanent siding you can trust the experts at Midtown. We believe in providing superior products from only the finest manufacturers. Give us a call at (630) 473-4165 for more information and a free quote!

"Midtown did my fence 4 years ago and we absolutely love the fence.They did a great job tearing out the existing fence and installing the brand new low maintenance fence. We are now getting a Bay window replaced with them.And we can't wait for it to get done.Thank you midtown. Cody did a great job helping us."

Daniel B on June 2025

Midtown Home Improvements is your neighborhood home improvement specialist. Whether you are looking for energy savings with Triple Pane Windows, a new low maintenance PVC Cellular deck, a maintenance free vinyl fence, or the thickest permanent siding you can trust the experts at Midtown. We believe in providing superior products from only the finest manufacturers. Give us a call at (630) 473-4165 for more information and a free quote!

"Midtown did my fence 4 years ago and we absolutely love the fence.They did a great job tearing out the existing fence and installing the brand new low maintenance fence. We are now getting a Bay window replaced with them.And we can't wait for it to get done.Thank you midtown. Cody did a great job helping us."

Daniel B on June 2025


Avatar for ASI Construction
ASI Construction
88 Burr Ridge Pkwy
5.00(
1
)
Approved Pro
ASI Construction
88 Burr Ridge Pkwy
5.00(
1
)
Approved Pro
71 local quotes requested
12 years of experience

Fully Licensed & Insured... and extremely well-rooted in the community... FREE ESTIMATES - 800-509-4724. ASI Construction is family owned and operated with over 30 years of owner experience. We provide general contracting and exterior remodeling services in residential and commercial roofing, siding, and gutters projects of all sizes, large and small. Essentially we are exterior remodeling and renovation project experts. We promise to provide you with a courteous and straightforward experience. Our philosophy is simple, we treat others the way we would like to be treated. Call NOW To Schedule A FREE Inspection!! 800-509-4274 (office) Admin@ConstructionByASI.com (email) www.ConstructionByASI.com (website

Fully Licensed & Insured... and extremely well-rooted in the community... FREE ESTIMATES - 800-509-4724. ASI Construction is family owned and operated with over 30 years of owner experience. We provide general contracting and exterior remodeling services in residential and commercial roofing, siding, and gutters projects of all sizes, large and small. Essentially we are exterior remodeling and renovation project experts. We promise to provide you with a courteous and straightforward experience. Our philosophy is simple, we treat others the way we would like to be treated. Call NOW To Schedule A FREE Inspection!! 800-509-4274 (office) Admin@ConstructionByASI.com (email) www.ConstructionByASI.com (website


GL Roofing
123 South Wolf Road
4.50(
1
)
Approved Pro
GL Roofing
123 South Wolf Road
4.50(
1
)
Approved Pro
Customers say: Quick response
Recommended by 100% of Angi customers
Recommended by 100% of HomeAdvisor customers
13 local quotes requested

GL Roofing is committed to quality work and excellent customer service. The level of our service and quality you'll get when you choose GL Roofing for your roofing needs is unmatched. We are fully staffed with highly talented and motivated individuals. We are excited that you have expressed an interest in our services and we look forward to working with you. Please call us today to discuss your roofing needs.

"Outstanding response time. Worked with the owner George who was also onsite for the job. Had a lot of knowledge about the issues we encountered along the way. Costs were very fair and reasonable. I would use him again."

Dave F on October 2024

GL Roofing is committed to quality work and excellent customer service. The level of our service and quality you'll get when you choose GL Roofing for your roofing needs is unmatched. We are fully staffed with highly talented and motivated individuals. We are excited that you have expressed an interest in our services and we look forward to working with you. Please call us today to discuss your roofing needs.

"Outstanding response time. Worked with the owner George who was also onsite for the job. Had a lot of knowledge about the issues we encountered along the way. Costs were very fair and reasonable. I would use him again."

Dave F on October 2024


Avatar for M & M ROOFING, INC. DBA M&M Home Remodeling Services
M & M ROOFING, INC. DBA M&M Home Remodeling Services
3488 Eagle Nest Dr
3.67(
3
)
Approved Pro
M & M ROOFING, INC. DBA M&M Home Remodeling Services
3488 Eagle Nest Dr
3.67(
3
)
Approved Pro
Customers say: Quick response
413 local quotes requested
7 years of experience

We are committed to excellence in every aspect of our business. We uphold a standard of integrity bound by fairness, honesty, and personal responsibility. Our distinction is the quality of service we bring to our customers. Accurate knowledge of our trade combined with ability is what makes us true professionals. Above all, we are watchful of our customers' interests, and make their concerns the basis of our business.

"On time professional excellent quality"

Kent W on April 2024

We are committed to excellence in every aspect of our business. We uphold a standard of integrity bound by fairness, honesty, and personal responsibility. Our distinction is the quality of service we bring to our customers. Accurate knowledge of our trade combined with ability is what makes us true professionals. Above all, we are watchful of our customers' interests, and make their concerns the basis of our business.

"On time professional excellent quality"

Kent W on April 2024


Avatar for Williams Roofing & Insulation, Inc.
Williams Roofing & Insulation, Inc.
6044 Carol Avenue
4.85(
534
)
Approved Pro
Williams Roofing & Insulation, Inc.
6044 Carol Avenue
4.85(
534
)
Approved Pro
Customers say: True professional
Recommended by 95% of Angi customers
Recommended by 95% of HomeAdvisor customers
24 local quotes requested

Why choose Williams Roofing & Insulation for your roofing needs? To start, we have decades of experience. Experience matters when protecting one of your most valuable assets, your home. We are a local, family owned and operated company serving the Chicagoland area- suburbs and surrounding areas. We are not storm chasers. We are familiar with local building codes. You know where to find us. Of course, we are licensed, insured and bonded. We offer one of the best labor warranties in the business- that's how confident we are with our craftmanship and products! We also do gutters, siding, chimneys, fascia, soffits, attic insulation and more. Quality workmanship and customer satisfaction are our top priorities. Call Williams Roofing & Insulation, Inc., today!

"Mark was great. He sat at my kitchen table and explained all my options and walked me through the process and what to expect. He did not try to upsell me anything he kept it simple. He was so professional I will also be using him to replace my gutters and I’ll be looking for other work for him in the future. "

David C on June 2025

Why choose Williams Roofing & Insulation for your roofing needs? To start, we have decades of experience. Experience matters when protecting one of your most valuable assets, your home. We are a local, family owned and operated company serving the Chicagoland area- suburbs and surrounding areas. We are not storm chasers. We are familiar with local building codes. You know where to find us. Of course, we are licensed, insured and bonded. We offer one of the best labor warranties in the business- that's how confident we are with our craftmanship and products! We also do gutters, siding, chimneys, fascia, soffits, attic insulation and more. Quality workmanship and customer satisfaction are our top priorities. Call Williams Roofing & Insulation, Inc., today!

"Mark was great. He sat at my kitchen table and explained all my options and walked me through the process and what to expect. He did not try to upsell me anything he kept it simple. He was so professional I will also be using him to replace my gutters and I’ll be looking for other work for him in the future. "

David C on June 2025


Avatar for A.S. Exteriors LLC
A.S. Exteriors LLC
2721 Westwood Drive #3A
5.00(
8
)
Approved Pro
A.S. Exteriors LLC
2721 Westwood Drive #3A
5.00(
8
)
Approved Pro
Free onsite estimate

We have the experience and we are committed to providing quality workmanship and superior customer service on all our applications. We at A.S. Exteriors LLC strive to maintain our reputation as a high quality, very service oriented company with our main focus being customer satisfaction.

"Antonio did a great job for me. Initially had him out just to clean my gutters. He also replaced one of my downspouts that had a hole in it while it was out here, for a really good price. Had no idea they did that kind of work as well. Very professional service , Highly recommend. "

Austin D on May 2025

We have the experience and we are committed to providing quality workmanship and superior customer service on all our applications. We at A.S. Exteriors LLC strive to maintain our reputation as a high quality, very service oriented company with our main focus being customer satisfaction.

"Antonio did a great job for me. Initially had him out just to clean my gutters. He also replaced one of my downspouts that had a hole in it while it was out here, for a really good price. Had no idea they did that kind of work as well. Very professional service , Highly recommend. "

Austin D on May 2025


Lupfer Builders, Inc.
3480 Tamarind Drive
5.00(
4
)
Approved Pro
Lupfer Builders, Inc.
3480 Tamarind Drive
5.00(
4
)
Approved Pro
Customers say: Quick response
Recommended by 100% of Angi customers
Recommended by 100% of HomeAdvisor customers
39 years of experience

We are a full-service remodeling company, specializing in, but not limited to; kitchens, baths, additions, basements, and more. Other services include: plumbing, electrical, tile, wood flooring, home repairs, and handyman services. Lupfer Builders, Inc., was established in 1994 by Dave Lupfer. A graduate of Northern Illinois University, Dave, comes to the construction industry with a wealth of experience. He began his career with Seigle’s Home Centers, managing site installations of Seigle products such as mill-work, doors, windows, and cabinetry. He also managed their retail electrical, and plumbing department as well. We are your one stop shop for all of your home improvement needs! Call us today, we look forward to earning your business.

"Efficient and neat."

Glenn B on May 2023

We are a full-service remodeling company, specializing in, but not limited to; kitchens, baths, additions, basements, and more. Other services include: plumbing, electrical, tile, wood flooring, home repairs, and handyman services. Lupfer Builders, Inc., was established in 1994 by Dave Lupfer. A graduate of Northern Illinois University, Dave, comes to the construction industry with a wealth of experience. He began his career with Seigle’s Home Centers, managing site installations of Seigle products such as mill-work, doors, windows, and cabinetry. He also managed their retail electrical, and plumbing department as well. We are your one stop shop for all of your home improvement needs! Call us today, we look forward to earning your business.

"Efficient and neat."

Glenn B on May 2023

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FAQs for asphalt shingle roofing installation and replacement projects in Winnetka, IL

Architectural shingles last 25 to 30 years, while standard 3-tab asphalt shingles last 15 to 20 years. This extended lifespan results from their thicker construction and higher-quality materials. Environmental factors such as extreme temperatures, strong winds, and heavy precipitation can affect longevity in any region. Regular maintenance, including clearing debris and addressing minor issues promptly, helps maximize the service life of either shingle type.

Architectural shingles justify their additional cost through superior longevity, enhanced durability, and better aesthetics. While they cost 20% to 40% more than standard 3-tab options, their longer lifespan (25 to 30 years versus 15 to 20) means fewer replacements over time. 

They also offer better resistance to wind and weather, a more attractive dimensional appearance, and stronger manufacturer warranties. For most homeowners, these benefits provide good value despite the higher initial investment.

30-year architectural shingles cost between $250 and $1,000 per square (100 square feet) installed. Premium brands tend toward the higher end of this spectrum, while more economical options fall in the lower range. These figures represent complete installation costs and don't include potential expenses for removing existing roofing materials, which can add disposal fees of $40 to $60 per ton.

Architectural shingles do require specific installation methods to ensure proper performance and warranty coverage. Their heavier weight and dimensional profile necessitate particular attention to underlayment quality, fastener placement, and overlap measurements. Manufacturer specifications must be followed precisely to maintain warranty protection. 

Professional installers understand these requirements and have the proper tools and training to implement them correctly. Improper installation can compromise both performance and warranty coverage, making professional installation particularly important for this premium roofing material.

The Winnetka, IL homeowners’ guide to asphalt shingle roofing installations and replacements
From average costs to expert advice, get all the answers you need to get your job done.
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