
Get matched with top roofers in Sleepy Hollow, IL
There are 31 highly-rated local roofers.
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TRUSTED BY SLEEPY HOLLOW, IL HOMEOWNERS
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Average homeowner rating1.8k+
Verified roofing services reviews
Verified Reviews for Roofing pros in Sleepy Hollow, IL
*The Angi rating for Roofing companies in Sleepy Hollow, IL is a rating based on verified reviews from our community of homeowners who have used these pros to meet their Roofing needs.
*The HomeAdvisor rating for Roofing companies in Sleepy Hollow, IL is a rating based on verified reviews from our community of homeowners who have used these pros to meet their Roofing needs.
Last update on November 30, 2025
Find Roofers in Sleepy Hollow
Rogers Roofing
Rogers Roofing
As experienced home improvement specialists, we seek to improve the industry’s reputation. Unlike many run-of-the-mill companies that offer undistinguished customer service and mediocre workmanship, Rogers Roofing raises the bar high. We are dedicated to providing homeowners with top-quality products and certified installation for a customer experience that’s second to none.
As experienced home improvement specialists, we seek to improve the industry’s reputation. Unlike many run-of-the-mill companies that offer undistinguished customer service and mediocre workmanship, Rogers Roofing raises the bar high. We are dedicated to providing homeowners with top-quality products and certified installation for a customer experience that’s second to none.

TruHome Pros
TruHome Pros
We pride ourselves on the quality work we provide, while delivering great customer service. Check out our services offered and call or click to schedule an estimate today!
"We can’t thank Gail and Brayden at TruHome Pros enough for their incredible help! My parents were having issues with their roof, including shingle loss and leaks into the attic. We reached out to Gail, and she immediately took action. She sent Brayden over right away, and he quickly secured the roof with a tarp to prevent further damage. Not only did they provide a temporary fix, but they also helped us get a brand-new roof on our 100-year-old home while preserving its charm. Their professionalism, responsiveness, and dedication to customer care were truly outstanding. Essentially saved the life of a family member. If you’re looking for a team that genuinely cares about your home, Gail and Brayden are the ones to call! Highly recommend!"
Cheyenne Y on June 2025
We pride ourselves on the quality work we provide, while delivering great customer service. Check out our services offered and call or click to schedule an estimate today!
"We can’t thank Gail and Brayden at TruHome Pros enough for their incredible help! My parents were having issues with their roof, including shingle loss and leaks into the attic. We reached out to Gail, and she immediately took action. She sent Brayden over right away, and he quickly secured the roof with a tarp to prevent further damage. Not only did they provide a temporary fix, but they also helped us get a brand-new roof on our 100-year-old home while preserving its charm. Their professionalism, responsiveness, and dedication to customer care were truly outstanding. Essentially saved the life of a family member. If you’re looking for a team that genuinely cares about your home, Gail and Brayden are the ones to call! Highly recommend!"
Cheyenne Y on June 2025

Infinity Exteriors LLC
Infinity Exteriors LLC
At Infinity Exteriors, we set ourselves apart through our unwavering commitment to quality, craftsmanship, and customer satisfaction. Our comprehensive services include roofing, siding, windows, and gutters, all delivered with meticulous attention to detail. Our team consists of seasoned Project Advisors, Managers, and Installers who bring years of industry experience, training, and a dedication to high standards, ensuring every project meets our strict quality guidelines. What makes us truly unique is our focus on each customer’s specific needs. We provide honest and free estimates that help homeowners make informed decisions, backed by transparent pricing and detailed project timelines. Infinity Exteriors’ team members are community-centered and customer-focused, often involved in local events, youth coaching, and charitable initiatives. This connection to our communities fosters a deeper commitment to integrity and personalized service. To guarantee the quality of our work, we use premium materials from trusted manufacturers and conduct thorough inspections at every project phase. Our commitment to excellence is further reinforced by industry-leading warranties, giving customers peace of mind that their investment is protected. When you choose Infinity Exteriors, you're partnering with a team dedicated not just to completing the job but to exceeding expectations at every turn.
"OUTSTANDING in every way! From Infinity's initial visit to the house, the project's PM, roof installation labours to infinity's post installation review. We experienced honest - trustworthy sales staff, clean hardworking roofers, quality materials & a final product which makes us proud to say this is out house. Thanks Infinity for a job your owner can be proud of."
Mike F on September 2018
At Infinity Exteriors, we set ourselves apart through our unwavering commitment to quality, craftsmanship, and customer satisfaction. Our comprehensive services include roofing, siding, windows, and gutters, all delivered with meticulous attention to detail. Our team consists of seasoned Project Advisors, Managers, and Installers who bring years of industry experience, training, and a dedication to high standards, ensuring every project meets our strict quality guidelines. What makes us truly unique is our focus on each customer’s specific needs. We provide honest and free estimates that help homeowners make informed decisions, backed by transparent pricing and detailed project timelines. Infinity Exteriors’ team members are community-centered and customer-focused, often involved in local events, youth coaching, and charitable initiatives. This connection to our communities fosters a deeper commitment to integrity and personalized service. To guarantee the quality of our work, we use premium materials from trusted manufacturers and conduct thorough inspections at every project phase. Our commitment to excellence is further reinforced by industry-leading warranties, giving customers peace of mind that their investment is protected. When you choose Infinity Exteriors, you're partnering with a team dedicated not just to completing the job but to exceeding expectations at every turn.
"OUTSTANDING in every way! From Infinity's initial visit to the house, the project's PM, roof installation labours to infinity's post installation review. We experienced honest - trustworthy sales staff, clean hardworking roofers, quality materials & a final product which makes us proud to say this is out house. Thanks Infinity for a job your owner can be proud of."
Mike F on September 2018

Bob the Builder Inc
Bob the Builder Inc
Now offering FREE Roof Inspections to establish WIND and HAIL damage. Proud winner of the 2013, 2014, 2015, 2016, 2017, 2018 and recently the 2019 Super Service Award. I personally supervise every job to insure that my clients vision becomes a reality.
"Bob the Builder installed new siding, gutters, facia and soffits on our house, along with reusing our new gutter guards from the old gutters. The quality of materials used and workmanship was top-notch. The entire project was executed flawlessly, and the cleanup was superb! The crew was not only efficient but also incredibly polite. I wouldn’t hesitate to use Bob the Builder again for any other project in the future, and I highly recommend them to anyone in need of siding services.""
Lynn W on September 2024
Now offering FREE Roof Inspections to establish WIND and HAIL damage. Proud winner of the 2013, 2014, 2015, 2016, 2017, 2018 and recently the 2019 Super Service Award. I personally supervise every job to insure that my clients vision becomes a reality.
"Bob the Builder installed new siding, gutters, facia and soffits on our house, along with reusing our new gutter guards from the old gutters. The quality of materials used and workmanship was top-notch. The entire project was executed flawlessly, and the cleanup was superb! The crew was not only efficient but also incredibly polite. I wouldn’t hesitate to use Bob the Builder again for any other project in the future, and I highly recommend them to anyone in need of siding services.""
Lynn W on September 2024

Jack's Roofing & Siding, LLC
Jack's Roofing & Siding, LLC
We are a locally owned and operated company that values honesty and integrity and treats your home improvement project as if it were our own. We offer a wide range of roofing expertise and experience to meet the specific needs of our clients. We specialize in a variety of roofing, to include asphalt shingle, traditional tile, natural slate, flat, foam, or single-ply. We pride ourselves on the quality of our work as well as our commitment to outstanding results. We look forward to building lasting relationships and guarantee your satisfaction!
We are a locally owned and operated company that values honesty and integrity and treats your home improvement project as if it were our own. We offer a wide range of roofing expertise and experience to meet the specific needs of our clients. We specialize in a variety of roofing, to include asphalt shingle, traditional tile, natural slate, flat, foam, or single-ply. We pride ourselves on the quality of our work as well as our commitment to outstanding results. We look forward to building lasting relationships and guarantee your satisfaction!

Montes Roofing, LLC
Montes Roofing, LLC
At Montes Roofing, we don’t just build roofs—we build trust. From expert craftsmanship to a rock-solid commitment to excellence, our team delivers results you can see and feel from start to finish. Whether it’s a new installation or a repair, we take pride in doing it right the first time. Got questions? Reach out today—we’re here to help protect what matters most!
"Great job completed everything on time "
Dean S on August 2025
At Montes Roofing, we don’t just build roofs—we build trust. From expert craftsmanship to a rock-solid commitment to excellence, our team delivers results you can see and feel from start to finish. Whether it’s a new installation or a repair, we take pride in doing it right the first time. Got questions? Reach out today—we’re here to help protect what matters most!
"Great job completed everything on time "
Dean S on August 2025

M&M Home Remodeling Services - Arlington Heights
M&M Home Remodeling Services - Arlington Heights
At M&M Home Remodeling Services, we specialize in high-quality exterior home improvements, including roofing, siding, windows, doors, gutters, and insulation. With decades of experience and a reputation built on integrity, craftsmanship, and customer satisfaction, we’re committed to helping homeowners enhance the comfort, value, and curb appeal of their homes. We offer industry-leading products, expert installation, and flexible financing options—including zero-interest plans—to make your project easy and affordable. From the first consultation to the final walkthrough, we’re here to deliver results you can trust and a home you’ll love.
"Did a wonderful job on our project. Helped to navigate us through the process."
Christina S on February 2025
At M&M Home Remodeling Services, we specialize in high-quality exterior home improvements, including roofing, siding, windows, doors, gutters, and insulation. With decades of experience and a reputation built on integrity, craftsmanship, and customer satisfaction, we’re committed to helping homeowners enhance the comfort, value, and curb appeal of their homes. We offer industry-leading products, expert installation, and flexible financing options—including zero-interest plans—to make your project easy and affordable. From the first consultation to the final walkthrough, we’re here to deliver results you can trust and a home you’ll love.
"Did a wonderful job on our project. Helped to navigate us through the process."
Christina S on February 2025

Allied Construction and Roofing, LLC
Allied Construction and Roofing, LLC
Allied Construction and Roofing - Your Premier Choice for Commercial and Residential Roofing Solutions! Are you in need of reliable roofing services for your commercial or residential property? Look no further! Allied Construction and Roofing is your trusted partner for all your roofing needs, providing exceptional craftsmanship and outstanding customer service. Why chooseAllied Construction and Roofing for your commercial and residential roofing needs? Expertise in Commercial and Residential Roofing: Our team of experienced professionals specializes in both commercial and residential roofing projects. We understand the unique requirements of each property type and have the knowledge to deliver superior results. Comprehensive Roofing Services: Whether you need a new roof installation, roof repairs, maintenance, or roof replacement, we offer a comprehensive range of services to cater to all your roofing needs. No project is too big or too small for us. Quality Materials and Workmansh
"I had just purchased a house. They came out and put white sealant on my flat roof. I have had water in my house for the past 7 months and hired a new roofer and they fixed it the right way and told me they basically did nothing with the white sealant. "
Allison M on September 2025
Allied Construction and Roofing - Your Premier Choice for Commercial and Residential Roofing Solutions! Are you in need of reliable roofing services for your commercial or residential property? Look no further! Allied Construction and Roofing is your trusted partner for all your roofing needs, providing exceptional craftsmanship and outstanding customer service. Why chooseAllied Construction and Roofing for your commercial and residential roofing needs? Expertise in Commercial and Residential Roofing: Our team of experienced professionals specializes in both commercial and residential roofing projects. We understand the unique requirements of each property type and have the knowledge to deliver superior results. Comprehensive Roofing Services: Whether you need a new roof installation, roof repairs, maintenance, or roof replacement, we offer a comprehensive range of services to cater to all your roofing needs. No project is too big or too small for us. Quality Materials and Workmansh
"I had just purchased a house. They came out and put white sealant on my flat roof. I have had water in my house for the past 7 months and hired a new roofer and they fixed it the right way and told me they basically did nothing with the white sealant. "
Allison M on September 2025
Midtown Home Improvements, Inc. (Chicago)
Midtown Home Improvements, Inc. (Chicago)
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 replaced all our siding and we are thrilled how it looks! Everything went smoothly from picking type and colors, scheduling, and installation. Cody and Peter watched over it all and made sure we were completely satisfied. The installers were very skilled and every detail was done by craftsmen. It turned out better than we we expected. thought it would."
Mike W on November 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 replaced all our siding and we are thrilled how it looks! Everything went smoothly from picking type and colors, scheduling, and installation. Cody and Peter watched over it all and made sure we were completely satisfied. The installers were very skilled and every detail was done by craftsmen. It turned out better than we we expected. thought it would."
Mike W on November 2025
Midtown Home Improvements, Inc. (Chicago)*
Midtown Home Improvements, Inc. (Chicago)*
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!
"Our deck is in severe shape. Cody is assured us we will get work done before winter so far we?ve paid >1/3 into the project &when we wanted to cancel, his boss said we would forfeit 33%. Our retirement. Being after three days of signing the contract with not 1 day sacrificed by the company we?ve caugt them in 7 ?lies/misinformations? so far. Our anxiety level is increasing as we see the concrete that will need to be poured in the winter time will be worthless making all the foundation of the deck Worthless at first we were told four days work, but then they said because of permits that it may take 2-3 weeks because of permits. They should?ve told us that in the beginning as we have mobility issues to get to our cars which will have to be moved off of property. The timing can?t be helped, but honesty can- if you?re faithful in small things, you?ll be faithful inlarge things we have to go through with the job because we can?t afford 33% of $24000. Trust is broken. Still waiting."
Jill E on November 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!
"Our deck is in severe shape. Cody is assured us we will get work done before winter so far we?ve paid >1/3 into the project &when we wanted to cancel, his boss said we would forfeit 33%. Our retirement. Being after three days of signing the contract with not 1 day sacrificed by the company we?ve caugt them in 7 ?lies/misinformations? so far. Our anxiety level is increasing as we see the concrete that will need to be poured in the winter time will be worthless making all the foundation of the deck Worthless at first we were told four days work, but then they said because of permits that it may take 2-3 weeks because of permits. They should?ve told us that in the beginning as we have mobility issues to get to our cars which will have to be moved off of property. The timing can?t be helped, but honesty can- if you?re faithful in small things, you?ll be faithful inlarge things we have to go through with the job because we can?t afford 33% of $24000. Trust is broken. Still waiting."
Jill E on November 2025
The Sleepy Hollow, IL homeowners’ guide to roofing services
From average costs to expert advice, get all the answers you need to get your job done.

A standing seam metal roof is a long-lasting, durable option for your home. Learn how much a standing seam metal roof costs and what can affect the price.
•Discover composite roof repair cost estimates. Learn what impacts pricing, how to save, and whether to repair or replace your composite roof.

Getting a wind mitigation inspection can work in your financial favor. Learn about the average wind mitigation inspection cost, including ways to save.

Not sure if you need a new roof yet? Check out these warning signs that you need a new roof to catch roof problems early.

A leaky roof is less than ideal. Learn how to patch a roof while you wait for repairs from the pros to prevent further damage to your home.

Shingles that are losing their granules may not be protecting your roof. Learn why shingle granule loss happens and what it means for your roof.
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