Top-rated roofers.

Get matched with top roofers in Chestnut Hill, MA

Enter your zip and get matched with up to 5 pros

Need a pro for your roofing project in Chestnut Hill, MA?

Select your specific project to find the pro for you.

TRUSTED BY CHESTNUT HILL, MA HOMEOWNERS

  • Average homeowner rating star icon4.3
    Average homeowner rating
  • Verified reviews icon2k+
    Verified roofing services reviews

Find Roofers in Chestnut Hill

"Great! Just one of the best home improvement vendors I’ve ever worked with. Excellent service and great work. Joe was super attentive to spotting and troubleshooting problem and worked incredibly well with our neighbors (we live in a brownstone). He worked quickly."

Brian L on September 2025

Hennelly & Son Roofing and Gutters is locally owned and operated, specializing in roofing, gutter installation, gutter cleaning, snow removal on roofs, and much more. Customer satisfaction is our top priority. Call us today for your free estimate!

"Great! Just one of the best home improvement vendors I’ve ever worked with. Excellent service and great work. Joe was super attentive to spotting and troubleshooting problem and worked incredibly well with our neighbors (we live in a brownstone). He worked quickly."

Brian L on September 2025


Avatar for MS Innovation Construction, Inc.

MS Innovation Construction, Inc.

4.89(
85
)
Approved Pro

MS Innovation Construction, Inc.

4.89(
85
)
Approved Pro
Customers say: Quality work
Recommended by 97% of Angi customers
Recommended by 97% of HomeAdvisor customers
7 years of experience

At MS Innovation Construction, Inc., we pride ourselves on providing quality service that our customers can believe in! We specialize in residential interior and exterior renovation and service Medway and the surrounding areas! We provide free estimates and look forward to earning your trust!

"Great job with adorable price"

Thompson J on November 2024

At MS Innovation Construction, Inc., we pride ourselves on providing quality service that our customers can believe in! We specialize in residential interior and exterior renovation and service Medway and the surrounding areas! We provide free estimates and look forward to earning your trust!

"Great job with adorable price"

Thompson J on November 2024


Avatar for Clear Choice Home Improvements

Clear Choice Home Improvements

4.83(
338
)
Approved Pro

Clear Choice Home Improvements

4.83(
338
)
Approved Pro
Customers say: Quality work
Recommended by 95% of Angi customers
Recommended by 95% of HomeAdvisor customers
22 years of experience

Clear Choice Home Improvements is New Hampshire's largest and New England's fastest growing Home Improvement Company. Family owned and operated, we provide truly personalized home remodeling services. At Clear Choice, we pride ourselves on presenting the best quality replacement windows, vinyl siding, roofing, bathroom systems, and gutter guards. Clear Choice will ALWAYS install these products in your home as if we were putting them into our own. Should those products ever need service, Clear Choice will ALWAYS be there to take care of any problems. We're confident that the home improvement products we install in your home are the absolute best in the industry.

"The crew was awesome, working in record heat wave for long days! Finished ahead of schedule and work was excellent."

Joe D on July 2024

Clear Choice Home Improvements is New Hampshire's largest and New England's fastest growing Home Improvement Company. Family owned and operated, we provide truly personalized home remodeling services. At Clear Choice, we pride ourselves on presenting the best quality replacement windows, vinyl siding, roofing, bathroom systems, and gutter guards. Clear Choice will ALWAYS install these products in your home as if we were putting them into our own. Should those products ever need service, Clear Choice will ALWAYS be there to take care of any problems. We're confident that the home improvement products we install in your home are the absolute best in the industry.

"The crew was awesome, working in record heat wave for long days! Finished ahead of schedule and work was excellent."

Joe D on July 2024


Avatar for LBJ Masonry

LBJ Masonry

4.98(
33
)
Approved Pro

LBJ Masonry

4.98(
33
)
Approved Pro
Super Service Award
Customers say: Quick response
29 years of experience
Free onsite estimate

Please call us at 6172564872 or email at [email protected] for a free quotation! We take great pride in our experience, expertise, quality, and customer service that we provide to meet the consumer's needs. It is our mission to provide excellent workmanship and complete customer satisfaction, from the start to the completion of a project. In order to understand the needs and expectations of our customers, we take great care to work and communicate with every customer in a professional manner. Our reputation is based on service, safety, and quality, regardless of how large or small the job.

"They an excellent job under difficult weather condition. They took down the box surrounding the chimney, took the chimney down to the roof line, replaced the flues and re-bricked the chimney. "

Charles C on December 2025

Please call us at 6172564872 or email at [email protected] for a free quotation! We take great pride in our experience, expertise, quality, and customer service that we provide to meet the consumer's needs. It is our mission to provide excellent workmanship and complete customer satisfaction, from the start to the completion of a project. In order to understand the needs and expectations of our customers, we take great care to work and communicate with every customer in a professional manner. Our reputation is based on service, safety, and quality, regardless of how large or small the job.

"They an excellent job under difficult weather condition. They took down the box surrounding the chimney, took the chimney down to the roof line, replaced the flues and re-bricked the chimney. "

Charles C on December 2025


Avatar for Ranch Roofing

Ranch Roofing

4.68(
669
)
Approved Pro

Ranch Roofing

4.68(
669
)
Approved Pro
Customers say: Quality work
30 years of experience
Free onsite estimate

Welcome to Ranch Roofing! Our goal is to provide our customers with the highest level of service and satisfaction. Please contact owner Bob O'Sullivan today for friendly, personalized and award winning service. 12 Months no interest, no payment, same as cash (ask for details).

"I wouldn't use any other company. Bob Sullivan, Roy Nagle, and the whole Ranch Roofing crew of professionals have reroofed my Arlington two-family house, fixed storm damage over the years, and just recently replaced the second-floor front and rear porches/roofs. It is beautiful. They are honest, accommodating, top-notch craftspeople, who really go out of their way to be customer focused. From start to finish I felt taken care of and was confident the work would be A+."

Celia D on March 2023

Welcome to Ranch Roofing! Our goal is to provide our customers with the highest level of service and satisfaction. Please contact owner Bob O'Sullivan today for friendly, personalized and award winning service. 12 Months no interest, no payment, same as cash (ask for details).

"I wouldn't use any other company. Bob Sullivan, Roy Nagle, and the whole Ranch Roofing crew of professionals have reroofed my Arlington two-family house, fixed storm damage over the years, and just recently replaced the second-floor front and rear porches/roofs. It is beautiful. They are honest, accommodating, top-notch craftspeople, who really go out of their way to be customer focused. From start to finish I felt taken care of and was confident the work would be A+."

Celia D on March 2023


Avatar for New Stage Home Improvement, Inc.

New Stage Home Improvement, Inc.

4.83(
106
)
Approved Pro

New Stage Home Improvement, Inc.

4.83(
106
)
Approved Pro
Super Service Award
Customers say: Quick response
18 years of experience
Free onsite estimate

New Stage Home Improvement Inc., has been in business for over 16 years with over 24 years of experience! We specialize in all your home improvement roofing needs and guarantee you a job well done! Whether a repair or a full on installation, we are your guys! We strive to exceed the home owners expectations each and every time and we get the job done the way you want it. We work in a timely fashion and always pay attention to detail. Call us today!

"Excellent company to deal with and quality job (new GAF system shingle garage roof installed). Easy to communicate with from start to finish. Jordan did the initial estimate and was always available by phone; likewise the office staff. The job took a half day. The supervisor and 4 workers worked very efficiently, removing the old roof, patching wood where necessary, putting new roof on, & cleaning up. Looks beautiful. And the garden was not damaged. "

Madeline W on July 2025

New Stage Home Improvement Inc., has been in business for over 16 years with over 24 years of experience! We specialize in all your home improvement roofing needs and guarantee you a job well done! Whether a repair or a full on installation, we are your guys! We strive to exceed the home owners expectations each and every time and we get the job done the way you want it. We work in a timely fashion and always pay attention to detail. Call us today!

"Excellent company to deal with and quality job (new GAF system shingle garage roof installed). Easy to communicate with from start to finish. Jordan did the initial estimate and was always available by phone; likewise the office staff. The job took a half day. The supervisor and 4 workers worked very efficiently, removing the old roof, patching wood where necessary, putting new roof on, & cleaning up. Looks beautiful. And the garden was not damaged. "

Madeline W on July 2025


Avatar for Mighty Dog Roofing MetroWest Boston

Mighty Dog Roofing MetroWest Boston

4.98(
29
)
Approved Pro

Mighty Dog Roofing MetroWest Boston

4.98(
29
)
Approved Pro
Customers say: Quick response
5 years of experience
Free onsite estimate

Our Mission at Mighty Dog Roofing is to be an industry changer, leading the industry with integrity, finding innovative ways to exceed the expectations of our clients and the communities we serve, and providing a customized experience each and every time we care for their home. Mighty Dog Roofing is endorsed by the nation's top manufacturers and distributors, offering our customers the best and most innovative products and services in the industry. Our relationships with these partners allow us to give you the best warranties, backed by our Watchdog Maintenance Program to take care of your home not just today, but for the life of your roof. Each project we finish is paw stamped with our seal of commitment to the expectations we set at the beginning of our relationship.

"Very Responsive!"

Glenn A on March 2024

Our Mission at Mighty Dog Roofing is to be an industry changer, leading the industry with integrity, finding innovative ways to exceed the expectations of our clients and the communities we serve, and providing a customized experience each and every time we care for their home. Mighty Dog Roofing is endorsed by the nation's top manufacturers and distributors, offering our customers the best and most innovative products and services in the industry. Our relationships with these partners allow us to give you the best warranties, backed by our Watchdog Maintenance Program to take care of your home not just today, but for the life of your roof. Each project we finish is paw stamped with our seal of commitment to the expectations we set at the beginning of our relationship.

"Very Responsive!"

Glenn A on March 2024


Avatar for Power Home Remodeling

Power Home Remodeling

4.76(
783
)
Approved Pro

Power Home Remodeling

4.76(
783
)
Approved Pro
Customers say: Quality work
Recommended by 94% of Angi customers
Recommended by 94% of HomeAdvisor customers
34 years of experience

As the nation’s largest full-service exterior home remodeler, we are backed by over 1,000+ Angi Super Service awards and more than one million happy customers. Why? Because we treat each job as an audition. An opportunity to prove ourselves to you. And the results speak for themselves. So make your home all it was meant to be with our unrivaled exterior services. Contact us today for a free, no obligation estimate on replacement windows, roofing, siding, doors, or attic insulation.

"This company completely took advantage of my MIL with high pressure sales. She did not need her roof redone yet they convinced her she needed it and 30k$ later she has a new roof she didn't need or want. You should be ashamed of yourselves."

Tim O on September 2025

As the nation’s largest full-service exterior home remodeler, we are backed by over 1,000+ Angi Super Service awards and more than one million happy customers. Why? Because we treat each job as an audition. An opportunity to prove ourselves to you. And the results speak for themselves. So make your home all it was meant to be with our unrivaled exterior services. Contact us today for a free, no obligation estimate on replacement windows, roofing, siding, doors, or attic insulation.

"This company completely took advantage of my MIL with high pressure sales. She did not need her roof redone yet they convinced her she needed it and 30k$ later she has a new roof she didn't need or want. You should be ashamed of yourselves."

Tim O on September 2025


Avatar for DC Carpenter, LLC

DC Carpenter, LLC

4.91(
143
)
Approved Pro

DC Carpenter, LLC

4.91(
143
)
Approved Pro
Super Service Award
Customers say: True professional
Recommended by 93% of Angi customers
Recommended by 93% of HomeAdvisor customers
24 years of experience

We are a locally family owned and operated company, that values honesty and integrity, and treats your home as if it were our own. We offer a variety of Decking, Window replacement, Fence, roofing and siding services, that are customizable to each individual project. You will find us to be competitively priced, paying close attention to the details of each and every project that we are involved with. We look forward to building lasting relationships, and guarantee your satisfaction!. Dear home owners, if you want contact me please go to my website and call from there.

"The guys did a terrific job! They were meticulous, hard working, used hand held sanders, brush painted…. I couldn’t have been happier with their work. They came when they said they would and communicated well thru text and email."

Karen P on October 2025

We are a locally family owned and operated company, that values honesty and integrity, and treats your home as if it were our own. We offer a variety of Decking, Window replacement, Fence, roofing and siding services, that are customizable to each individual project. You will find us to be competitively priced, paying close attention to the details of each and every project that we are involved with. We look forward to building lasting relationships, and guarantee your satisfaction!. Dear home owners, if you want contact me please go to my website and call from there.

"The guys did a terrific job! They were meticulous, hard working, used hand held sanders, brush painted…. I couldn’t have been happier with their work. They came when they said they would and communicated well thru text and email."

Karen P on October 2025


Avatar for Doherty Slate Roofing

Doherty Slate Roofing

4.98(
56
)
Approved Pro

Doherty Slate Roofing

4.98(
56
)
Approved Pro
Super Service Award
Customers say: Quality work
Recommended by 91% of Angi customers
Recommended by 91% of HomeAdvisor customers
26 years of experience

"Doherty Slate Roofing: We are slate copper specialists and an award-winning company. Our craftsmanship is prestigious. Unlike other companies, we match identical roof slates to existing slate roofs. This means slate size, slate color, slate age, and thickness to conduct slate roof repairs. Design and install high-end custom copper roof work, Copper Gutters, and install rubber roofs. Were veteran owned and operated, LGBTQ+ Friendly. We strive to be the leading slate roofing company in the Boston, Newton, and Wellesley areas. We also repair slate tile and carry out annual drone slate roof inspections, slate repairs, slate restoration, and slate installation. If you're searching for a slate roofer near me, we are your slate roofing contractor.

"If you need slate (or copper) work done, I would have Doherty Slate Roofing come out and look at the job. Jason's quote was far better than any of the other roofing companies. I am very satisfied with the work done, and to top it all off, Jason and his crew are just very nice people to work with. I will be using his services for many years to come."

Paul W on October 2025

"Doherty Slate Roofing: We are slate copper specialists and an award-winning company. Our craftsmanship is prestigious. Unlike other companies, we match identical roof slates to existing slate roofs. This means slate size, slate color, slate age, and thickness to conduct slate roof repairs. Design and install high-end custom copper roof work, Copper Gutters, and install rubber roofs. Were veteran owned and operated, LGBTQ+ Friendly. We strive to be the leading slate roofing company in the Boston, Newton, and Wellesley areas. We also repair slate tile and carry out annual drone slate roof inspections, slate repairs, slate restoration, and slate installation. If you're searching for a slate roofer near me, we are your slate roofing contractor.

"If you need slate (or copper) work done, I would have Doherty Slate Roofing come out and look at the job. Jason's quote was far better than any of the other roofing companies. I am very satisfied with the work done, and to top it all off, Jason and his crew are just very nice people to work with. I will be using his services for many years to come."

Paul W on October 2025

...
Showing 1-10 of 1475
Roofing questions, answered by experts

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.

After you've chosen the best roofer for you, schedule an inspection and review the final contract. Your roofing company should be able to provide options for scheduling the work and a potential timeline for obtaining the permits and starting the job. Remember to always request everything in writing before work begins.

Some homes, like those with flat roofs, may not have eaves at all. Some contemporary-style homes also lack eaves, although many may have abbreviated eaves to divert water and protect the walls and foundation. Homes without eaves often have specific types of gutters affixed directly to the edge of the roof to provide adequate drainage.

If your roof has a vapor barrier, you will need approximately one square foot of roof vent for every 300 square feet of ceiling space. If there is no vapor barrier, the roof should have one square foot of roof vent for every 150 square feet of ceiling space. If you are not comfortable making this determination, a local roofing professional can help.

Tar and gravel roofs last an average of 30 years, which is longer than the average lifespan of many other flat roofs. The gravel on top of the waterproof membrane helps protect the roof from UV damage and physical damage, so if you keep your roof drains clear and carry out annual roof inspections to catch issues early, you could see up to 40 years of useful life from your roof.

The Chestnut Hill, MA homeowners’ guide to roofing services

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

What do you need done? We’ll find top pros.
  • 🌱 "Mow a small front yard"
  • 🛠 "Fix a leaking pipe under the sink"
  • 🏠 "Repair shingles on an asphalt roof"