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Find Asphalt shingle roofing installers and replacers in Chestnut Hill

Avatar for Power Home Remodeling

Power Home Remodeling

4.50(
344
)
Approved Pro

Power Home Remodeling

4.50(
344
)
Approved Pro
Customers say: Super punctual
2946 local quotes requested
34 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/.

"he was here all over the house a and refuse to give me a estimate because of my gender and waste my time, give me a terrible experience. "

Anna B on January 2026

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/.

"he was here all over the house a and refuse to give me a estimate because of my gender and waste my time, give me a terrible experience. "

Anna B on January 2026


Connection General Construction, Inc.

5.00(
2
)
Approved Pro

Connection General Construction, Inc.

5.00(
2
)
Approved Pro
Customers say: Quick response
Recommended by 100% of Angi customers
Recommended by 100% of HomeAdvisor customers
4 years of experience

At CONNECTION GENERAL CONSTRUCTION INC we pride our company on reliability, great communication, integrity, and quality work. We are experts in our trade and will do our best to keep you as educated as we can on your particular task or project. We look forward to earning your business!

"This company is easy to work also fast clean and good communication. I really recommend."

Lucas S on February 2024

At CONNECTION GENERAL CONSTRUCTION INC we pride our company on reliability, great communication, integrity, and quality work. We are experts in our trade and will do our best to keep you as educated as we can on your particular task or project. We look forward to earning your business!

"This company is easy to work also fast clean and good communication. I really recommend."

Lucas S on February 2024


Avatar for SB Roofing & Construction, Inc.

SB Roofing & Construction, Inc.

5.00(
1
)
Approved Pro

SB Roofing & Construction, Inc.

5.00(
1
)
Approved Pro
Customers say: Quick response
Recommended by 100% of Angi customers
Recommended by 100% of HomeAdvisor customers
20 years of experience

Welcome to SB Roofing & Construction INC! We take pride in the quality of work and customer satisfaction that we give each and every customer! We are known to pay exquisite attention to detail while making customer satisfaction our top priority. Call us today to learn more about how we can help you!

"They were very organized and left the house (yard) clean of any debris. The roof looks great and their price is very competitive."

Shirley C on April 2023

Welcome to SB Roofing & Construction INC! We take pride in the quality of work and customer satisfaction that we give each and every customer! We are known to pay exquisite attention to detail while making customer satisfaction our top priority. Call us today to learn more about how we can help you!

"They were very organized and left the house (yard) clean of any debris. The roof looks great and their price is very competitive."

Shirley C on April 2023


Avatar for Master Roof, Inc.

Master Roof, Inc.

4.93(
46
)
Approved Pro

Master Roof, Inc.

4.93(
46
)
Approved Pro
Customers say: True professional
26 years of experience
Free onsite estimate

We have been in the business for more than 20 years. Second-generation family-owned company, and we are proud of it. Our motto is "su casa es mi casa ". Our number one priority is customer satisfaction. Our goal is to achieve your peace of mind before, during, and after each project. We specialize in roofing, siding, and gutters. Call us for quotes or repairs. FREE estimates.

"Excellent company to do business with. Great job from start to completion. We were more than satisfied with the quality of work and their communication with us throughout the job. We highly recommend this company"

jerry t on November 2025

We have been in the business for more than 20 years. Second-generation family-owned company, and we are proud of it. Our motto is "su casa es mi casa ". Our number one priority is customer satisfaction. Our goal is to achieve your peace of mind before, during, and after each project. We specialize in roofing, siding, and gutters. Call us for quotes or repairs. FREE estimates.

"Excellent company to do business with. Great job from start to completion. We were more than satisfied with the quality of work and their communication with us throughout the job. We highly recommend this company"

jerry t on November 2025


Avatar for Willard Co

Willard Co

4.91(
140
)
Approved Pro

Willard Co

4.91(
140
)
Approved Pro
Customers say: Super punctual
Recommended by 96% of Angi customers
Recommended by 96% of HomeAdvisor customers
16 local quotes requested

The Willard Company is a full service residential and commercial roofing company specializing in asphalt, copper, slate, tile, and wood (cedar) shingles, and rubber roofing. We install all types of siding. Parker M. Willard Jr., our 5th generation family member, is our General Manager with over 30 years of experience in the business. The Willard Company is fully licensed, trained and certified to give you the best products and workmanship at a fair and reasonable price. We still stand behind our workmanship longer than anyone in the industry and we pride ourselves on our service AFTER the job is complete. Massachusetts Home Improvement Contractor's Registration #106642. Construction Supervisor's License #085926.

"Excellent service. And quick issue resolution. I would definitely hire again"

Naeemah E on May 2022

The Willard Company is a full service residential and commercial roofing company specializing in asphalt, copper, slate, tile, and wood (cedar) shingles, and rubber roofing. We install all types of siding. Parker M. Willard Jr., our 5th generation family member, is our General Manager with over 30 years of experience in the business. The Willard Company is fully licensed, trained and certified to give you the best products and workmanship at a fair and reasonable price. We still stand behind our workmanship longer than anyone in the industry and we pride ourselves on our service AFTER the job is complete. Massachusetts Home Improvement Contractor's Registration #106642. Construction Supervisor's License #085926.

"Excellent service. And quick issue resolution. I would definitely hire again"

Naeemah E on May 2022


Avatar for M. Gendron and Son Construction, LLC

M. Gendron and Son Construction, LLC

4.96(
84
)
Approved Pro

M. Gendron and Son Construction, LLC

4.96(
84
)
Approved Pro
Customers say: Quality work
Recommended by 96% of Angi customers
Recommended by 96% of HomeAdvisor customers
28 years of experience

M. Gendron and Son Construction, LLC are a southern New Hampshire based construction company specializing in roofing, vinyl siding, windows, additions, demolition and much more. We are fully licensed and insured construction company providing year round service to residential, commercial, and property management customers. We are also OSHA and LEAD Safe certified and also carry a A+ rating with the BBB. Call us today for your free no obligation estimate. Ask about the different types of roofing systems we have available. We have systems for every budget! FINANCING AVAILABLE to those who qualify

"Mike from MGS responded immediately to my request from Angi for a roofing contractor. He came for an estimate the following day. He gave us a price that was half of another competitor - plus replacing a large skylight. The price included the permit and dumpster. He explained everything thoroughly and answered all our questions - and we didn't have to sit through a two-hour sales pitch. All materials were top quality and installed above standard practice. This was in December and we were concerned about the weather and short daylight. Mike assured us they should have the job done in a day, barring some unexpected repairs to the roof. Their crew came a week later. Crew leader Rick was fantastic.They stripped two layers of ashphalt shingles off the house, breezeway and garage, replaced the skylight, and were done in about seven hours. This included replacing the lead flashing around the chimney and building a cricket above it to divert the water..Amazing! They spent about another hour thouroughly cleaning up all the debris around the property, including scouring for nails with a large rolling magnet. The dumpster was picked up two days later. Except for the great looking new roof, the property looks like like they were never here. We had three days of rain starting a few hours after they left, and the house is completely dry. This was one of the most pleasant experiences I've had dealing with a contractor. From start to finish, everyone has been friendly, respectful and professional. Mike was in constant contact with us throughout the process and responded immediately if I had.question. I highly recommend MGS for any roofing job."

Ken D on January 2024

M. Gendron and Son Construction, LLC are a southern New Hampshire based construction company specializing in roofing, vinyl siding, windows, additions, demolition and much more. We are fully licensed and insured construction company providing year round service to residential, commercial, and property management customers. We are also OSHA and LEAD Safe certified and also carry a A+ rating with the BBB. Call us today for your free no obligation estimate. Ask about the different types of roofing systems we have available. We have systems for every budget! FINANCING AVAILABLE to those who qualify

"Mike from MGS responded immediately to my request from Angi for a roofing contractor. He came for an estimate the following day. He gave us a price that was half of another competitor - plus replacing a large skylight. The price included the permit and dumpster. He explained everything thoroughly and answered all our questions - and we didn't have to sit through a two-hour sales pitch. All materials were top quality and installed above standard practice. This was in December and we were concerned about the weather and short daylight. Mike assured us they should have the job done in a day, barring some unexpected repairs to the roof. Their crew came a week later. Crew leader Rick was fantastic.They stripped two layers of ashphalt shingles off the house, breezeway and garage, replaced the skylight, and were done in about seven hours. This included replacing the lead flashing around the chimney and building a cricket above it to divert the water..Amazing! They spent about another hour thouroughly cleaning up all the debris around the property, including scouring for nails with a large rolling magnet. The dumpster was picked up two days later. Except for the great looking new roof, the property looks like like they were never here. We had three days of rain starting a few hours after they left, and the house is completely dry. This was one of the most pleasant experiences I've had dealing with a contractor. From start to finish, everyone has been friendly, respectful and professional. Mike was in constant contact with us throughout the process and responded immediately if I had.question. I highly recommend MGS for any roofing job."

Ken D on January 2024


Avatar for GF Sprague & Company, Inc.

GF Sprague & Company, Inc.

4.54(
285
)
Approved Pro

GF Sprague & Company, Inc.

4.54(
285
)
Approved Pro
Customers say: Super punctual
19 local quotes requested
57 years of experience

Your Home. Your Priorities. Our Expertise. For more than half a century, GF Sprague has been a growing part of Boston’s architectural fabric. We began by restoring slate roofs and hand-forming copper details for some of the area’s most historic sites and city buildings. These weren’t just jobs, they were lessons in precision and pride. Slate and copper demanded true craftsmanship, the kind that can’t be rushed or faked. That craftsmanship is our foundation. As Boston grew we did too, expanding to help homeowners in the surrounding towns. We wanted to bring the same standard of excellence required on those historic projects to everyone. Today, GF Sprague adds on to our traditional roofing specialties with asphalt, rubber, and cedar. -In addition to our copperwork we can also work on chimneys, gutters, windows, and siding, Whether it’s a 100-year-old brownstone or an updated colonial home, we bring the same commitment to detail, durability, and integrity that defined us on day one. What truly sets GF Sprague apart isn’t just our skill, it’s our promise to treat every customer like family. Every roof we install is a promise: to protect a family and carry forward Boston’s tradition of homes built to last. Along with that promise is another, our Best Price Promise. This means you get the best price for your project every time. Many of our clients have trusted us for generations, passing down their loyalty just as we’ve passed down our craft. With GF Sprague, you don’t just get a contractor — you gain a lifelong, local partner in caring for your home’s exterior.

"Very impressed with Sprague, Mark was very knowledgeable and straightforward. Crew was first class closing roofing and Clean Up in four days and cold weather. Justin was terrific, personable and responsive, and was always on site or available. Crew and especially Foreman were excellent. I would recommend GF Sprague for a high quality Job, their technology and customer service."

Stephen R on January 2023

Your Home. Your Priorities. Our Expertise. For more than half a century, GF Sprague has been a growing part of Boston’s architectural fabric. We began by restoring slate roofs and hand-forming copper details for some of the area’s most historic sites and city buildings. These weren’t just jobs, they were lessons in precision and pride. Slate and copper demanded true craftsmanship, the kind that can’t be rushed or faked. That craftsmanship is our foundation. As Boston grew we did too, expanding to help homeowners in the surrounding towns. We wanted to bring the same standard of excellence required on those historic projects to everyone. Today, GF Sprague adds on to our traditional roofing specialties with asphalt, rubber, and cedar. -In addition to our copperwork we can also work on chimneys, gutters, windows, and siding, Whether it’s a 100-year-old brownstone or an updated colonial home, we bring the same commitment to detail, durability, and integrity that defined us on day one. What truly sets GF Sprague apart isn’t just our skill, it’s our promise to treat every customer like family. Every roof we install is a promise: to protect a family and carry forward Boston’s tradition of homes built to last. Along with that promise is another, our Best Price Promise. This means you get the best price for your project every time. Many of our clients have trusted us for generations, passing down their loyalty just as we’ve passed down our craft. With GF Sprague, you don’t just get a contractor — you gain a lifelong, local partner in caring for your home’s exterior.

"Very impressed with Sprague, Mark was very knowledgeable and straightforward. Crew was first class closing roofing and Clean Up in four days and cold weather. Justin was terrific, personable and responsive, and was always on site or available. Crew and especially Foreman were excellent. I would recommend GF Sprague for a high quality Job, their technology and customer service."

Stephen R on January 2023


Avatar for Nelson Builder LLC

Nelson Builder LLC

5.00(
3
)
Approved Pro

Nelson Builder LLC

5.00(
3
)
Approved Pro
Super Service Award
42 years of experience
Free onsite estimate

Whether you're looking to build a new home, renovate an existing one, or need custom cabinetry and millwork, we've got you covered. No job is too small for us, we take pride in delivering high-quality work that meets your unique needs and exceeds your expectations. Contact us today to learn more about how we can help bring your vision to life!

"Nelson did a great job at my home. After discovering a water leak in the kitchen, he quickly made the first repair to stop the water loss. He then helped me through all the insurance steps so that I could get the best possible coverage. The result could not have been better, my new kitchen exceeded my expectations. Thank you Nelson and your team for the quick and efficient work."

Claudia L on April 2025

Whether you're looking to build a new home, renovate an existing one, or need custom cabinetry and millwork, we've got you covered. No job is too small for us, we take pride in delivering high-quality work that meets your unique needs and exceeds your expectations. Contact us today to learn more about how we can help bring your vision to life!

"Nelson did a great job at my home. After discovering a water leak in the kitchen, he quickly made the first repair to stop the water loss. He then helped me through all the insurance steps so that I could get the best possible coverage. The result could not have been better, my new kitchen exceeded my expectations. Thank you Nelson and your team for the quick and efficient work."

Claudia L on April 2025


Avatar for Cornerstone Building Associates LLC

Cornerstone Building Associates LLC

4.92(
18
)
Approved Pro

Cornerstone Building Associates LLC

4.92(
18
)
Approved Pro
Super Service Award
Customers say: True professional
Recommended by 94% of Angi customers
Recommended by 94% of HomeAdvisor customers
54 years of experience

Hello! I’m Eric and I have the great pleasure of running the day to day operations of my family business! A little about myself, I was taught everything I know by my Grandfather and my Father who are both amazing craftsman. I have been working to emulate their skill for the last 15 years! The work we do is truly a monument to their legacy, so you can be assured it’s top notch. We aim to treat every client like a neighbor (one we really like). So please, give us the opportunity to prove that honestly and reliably are still staples of success

"Great response time, excellent pricing, friendly service."

Christopher N on December 2024

Hello! I’m Eric and I have the great pleasure of running the day to day operations of my family business! A little about myself, I was taught everything I know by my Grandfather and my Father who are both amazing craftsman. I have been working to emulate their skill for the last 15 years! The work we do is truly a monument to their legacy, so you can be assured it’s top notch. We aim to treat every client like a neighbor (one we really like). So please, give us the opportunity to prove that honestly and reliably are still staples of success

"Great response time, excellent pricing, friendly service."

Christopher N on December 2024


Avatar for AJ Exterior

AJ Exterior

4.51(
78
)
Approved Pro

AJ Exterior

4.51(
78
)
Approved Pro
Customers say: Quality work
22 years of experience
Free onsite estimate

Here at A.J. Exterior we have been in business for three generations, in and around the Boston area! We and I have a reputation for honest work, excellent customer service and a job completed as if it were my own home. We demand it! We specialize in replacement roofs and the installation of vinyl siding. We use only top quality materials and allow only the best craftsman in the business to perform your work. One of us is present on each and every job to ensure proper installation. This is important to validate our extended factory warranties, and to supervise all aspects of the project. If you are in need of these services, please call AJ Exteriors, and let us send one of our knowledgeable project managers to give you a free estimate and some good advice before making any commitments. We have low overhead and that allows us to keep the cost down for a quality job performed on your home! Call us last to compare or just call us first for a job done right.

"My comments are on the BBB page ED is not a MAN! of his word there was so many things that needed fixing and he never came back to fix he also hired Mexicans to do my steps both sides of my house which they left water bottles pieces of the remainder of the steps they did not need under the steps and covered the sides my front porch you can see some of the insulation he supposed to come back and fix my house is white and slate and where the poles are that are connected to the overhead roof there is two plain wood blocks up there totally noticeable they should?ve been painted white he said he?ll come back and take care of that didn?t happen when he finished the vinyl siding, he said if I hire him to do my steps, he will do the roof that?s in the back of my house for free. He has not done that he told me it will cost $16,500 for my steps he was filling out the contract, he added $1000 more without even telling me I noticed that and spoke on it. He said the extra was for materials. "

Katrina R on August 2025

Here at A.J. Exterior we have been in business for three generations, in and around the Boston area! We and I have a reputation for honest work, excellent customer service and a job completed as if it were my own home. We demand it! We specialize in replacement roofs and the installation of vinyl siding. We use only top quality materials and allow only the best craftsman in the business to perform your work. One of us is present on each and every job to ensure proper installation. This is important to validate our extended factory warranties, and to supervise all aspects of the project. If you are in need of these services, please call AJ Exteriors, and let us send one of our knowledgeable project managers to give you a free estimate and some good advice before making any commitments. We have low overhead and that allows us to keep the cost down for a quality job performed on your home! Call us last to compare or just call us first for a job done right.

"My comments are on the BBB page ED is not a MAN! of his word there was so many things that needed fixing and he never came back to fix he also hired Mexicans to do my steps both sides of my house which they left water bottles pieces of the remainder of the steps they did not need under the steps and covered the sides my front porch you can see some of the insulation he supposed to come back and fix my house is white and slate and where the poles are that are connected to the overhead roof there is two plain wood blocks up there totally noticeable they should?ve been painted white he said he?ll come back and take care of that didn?t happen when he finished the vinyl siding, he said if I hire him to do my steps, he will do the roof that?s in the back of my house for free. He has not done that he told me it will cost $16,500 for my steps he was filling out the contract, he added $1000 more without even telling me I noticed that and spoke on it. He said the extra was for materials. "

Katrina R on August 2025

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FAQs for asphalt shingle roofing installation and replacement projects in Chestnut Hill, MA

Roofing professionals can usually install a medium-sized asphalt shingle roof in two to three days. Installation time increases if your roof is particularly steep or difficult to access or has features like chimneys or skylights that roofers must work around.

Three-tab asphalt shingles usually have the lowest upfront cost of any roofing shingle material. They’re sturdy and typically last 15 to 20 years. However, they may have a shorter lifespan in especially hot or cold climates. Talk to a local roofing professional about the best materials for your climate. In some cases, materials with a higher upfront cost may save you more on repairs or replacements in the long run.

Start by multiplying the length by the width of your roof to calculate the square footage. Most shingle replacement costs $4 to $12 per square foot for materials and labor, depending on factors like the material and the slope of your roof. Once you know the size of your roof, you can calculate a rough estimate of total costs or contact a local roofing professional to provide you with a custom quote.

Asphalt shingles are generally considered to be a low-maintenance item. However, cleaning your asphalt roofing can help prolong the lifespan and keep it looking fresh. If you’re comfortable with DIY and have the proper equipment, you may be able to clean your asphalt shingles yourself. However, if you have an especially high or steep roof, it’s usually safer to hire a professional roof cleaner.

The Chestnut Hill, MA 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.