Top-rated asphalt shingle roofing installers and replacers.

Get matched with top asphalt shingle roofing installers and replacers in Winchester, MA

Enter your zip and get matched with up to 3 pros

Matching on HomeAdvisor

Share some details icon
Share some details about your home project.
Match with local pros icon
Within moments, match with highly-rated local pros.
Compare quotes icon
Compare quotes and choose the best pro for the job.

Find Asphalt shingle roofing installers and replacers in Winchester

Avatar for Power Home Remodeling

Power Home Remodeling

4.51(
343
)
Approved Pro

Power Home Remodeling

4.51(
343
)
Approved Pro
Customers say: Super punctual
2501 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/.

"The work was done quickly and the lead time was short."

Glenn S on November 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/.

"The work was done quickly and the lead time was short."

Glenn S on November 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
4 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


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
3 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
19 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 Newton Roofing Residential

Newton Roofing Residential

4.67(
141
)
Approved Pro

Newton Roofing Residential

4.67(
141
)
Approved Pro
Customers say: Quality work
Recommended by 90% of Angi customers
Recommended by 90% of HomeAdvisor customers
36 years of experience

Dear Prospective Customer, Newton Roofing Residential is a woman owned, professional roofing contractor serving the Boston area with a hands on approach and over 30 years of roofing management experience. If you are looking for a reputable company for your roofing project, and quality, integrity, and distinguished customer service are important, You’ve found your roofer I founded Newton Roofing Residential on two principals, treat our customers with respect and stand behind our work. Countless times, we go to a new customer’s home to diagnose a leak only to find a new, yet poorly installed, roof is the issue. It is troubling to see how many homeowners are victimized by shoddy Massachusetts roofing contractors. To top it off, many are dismayed to find their roof was installed by a non certified roofer, and no manufacturer will honor their warranty. We at Newton Roofing Residential are well trained and constantly stay abreast of the latest product improvements. Our dedication to professionalism allows us to offer some of the most comprehensive warranties in the industry. Although we are confident in the quality of our roofing systems, on the rare chance there is ever an issue, with our workmanship or product failure, we have you covered and will come back and fix it. When you take into consideration our available lifetime warranties, our “service first” mentality, and our sincere wish to become your partner in your roofing needs, we are the Massachusetts Roofing Contractor for your next roofing project. Whether you need a new roof, a simple repair, or just want to deal with an honest, professional, quality-orientated roofing company, you won’t regret it. Thank you for your business. Founder and CEO Toni Bryan Please give us a call with all your roofing needs. (617) 244-9901.

"I would not recommend them. Initially it appeared they did a good job on my rubber roof, so I hired them again for full gutters, which they subcontracted out. Within the year I had a large leak develop behind their new gutter. They acknowledged the problem but it took months, and constant badgering by email and phone, to get them to come back and fix the problem. They tried a temporary fix with sealer, which failed in weeks, and then it took weeks longer to get them to come back and install a fascia apron. The next year, my rubber roof leaked where they had flashed it. Again it took months to get them to come back and look at it, with constant badgering. When they came back they applied a copious amount of sealer and told me that I had a rot problem with a wooden railing that I would need a carpenter for, and that they would send me photographs and suggestions for repair. They never replied after that, and the leak continued despite their sealing attempt. I finally gave up and found a new roofer, who tells me that they did an inferior job in the first place, and the repair is costing me thousands of dollars."

Ednan B on October 2021

Dear Prospective Customer, Newton Roofing Residential is a woman owned, professional roofing contractor serving the Boston area with a hands on approach and over 30 years of roofing management experience. If you are looking for a reputable company for your roofing project, and quality, integrity, and distinguished customer service are important, You’ve found your roofer I founded Newton Roofing Residential on two principals, treat our customers with respect and stand behind our work. Countless times, we go to a new customer’s home to diagnose a leak only to find a new, yet poorly installed, roof is the issue. It is troubling to see how many homeowners are victimized by shoddy Massachusetts roofing contractors. To top it off, many are dismayed to find their roof was installed by a non certified roofer, and no manufacturer will honor their warranty. We at Newton Roofing Residential are well trained and constantly stay abreast of the latest product improvements. Our dedication to professionalism allows us to offer some of the most comprehensive warranties in the industry. Although we are confident in the quality of our roofing systems, on the rare chance there is ever an issue, with our workmanship or product failure, we have you covered and will come back and fix it. When you take into consideration our available lifetime warranties, our “service first” mentality, and our sincere wish to become your partner in your roofing needs, we are the Massachusetts Roofing Contractor for your next roofing project. Whether you need a new roof, a simple repair, or just want to deal with an honest, professional, quality-orientated roofing company, you won’t regret it. Thank you for your business. Founder and CEO Toni Bryan Please give us a call with all your roofing needs. (617) 244-9901.

"I would not recommend them. Initially it appeared they did a good job on my rubber roof, so I hired them again for full gutters, which they subcontracted out. Within the year I had a large leak develop behind their new gutter. They acknowledged the problem but it took months, and constant badgering by email and phone, to get them to come back and fix the problem. They tried a temporary fix with sealer, which failed in weeks, and then it took weeks longer to get them to come back and install a fascia apron. The next year, my rubber roof leaked where they had flashed it. Again it took months to get them to come back and look at it, with constant badgering. When they came back they applied a copious amount of sealer and told me that I had a rot problem with a wooden railing that I would need a carpenter for, and that they would send me photographs and suggestions for repair. They never replied after that, and the leak continued despite their sealing attempt. I finally gave up and found a new roofer, who tells me that they did an inferior job in the first place, and the repair is costing me thousands of dollars."

Ednan B on October 2021


Avatar for AJ Exterior

AJ Exterior

4.51(
78
)
Approved Pro

AJ Exterior

4.51(
78
)
Approved Pro
Customers say: Quality work
21 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


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
17 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 Diamond Construction Inc

Diamond Construction Inc

4.81(
81
)
Approved Pro

Diamond Construction Inc

4.81(
81
)
Approved Pro
Customers say: True professional
Recommended by 92% of Angi customers
Recommended by 92% of HomeAdvisor customers
40 local quotes requested

Diamond Construction, Inc. has built a reputation on quality with honesty and integrity. We employ only the highest trained, professional roofers for our team. We partner with the highest quality shingle manufacturers, and we hand-nail all roofs to ensure quality installation as well. At the end of every project, our supervisor will do an inspection with the homeowner to ensure their satisfaction. At Diamond Construction our mission is to ensure peace of mind for each customer through exceptional service. We work hard to exceed our customers' expectations. Our quality and experience combined with our strong work ethic are only some of the reasons why we maintain an A+ rating on the BBB and Home Advisor - Pro. We are certified by GAF and CertainTeed. 100% Customer Satisfaction Guaranteed. Licensed, Insured, and Accredited Roofers. Convenient Evening & Weekend Appointments. Financing available. Affordable Roofing & Remodeling Quality. New England Premier Roofing Contractor. Additional Email at: office@diamondconstructionma.com

"Did a great Job with roof and helped me with the insurance claim from the storm damage to roof. They are prompt, clean, and super nice. Anything they moved potted plants, my deck furniture , was put back in place with care. They went over yard with a magnet device to get any loose nails , etc that may have fallen in grass. "

Cecile B on October 2025

Diamond Construction, Inc. has built a reputation on quality with honesty and integrity. We employ only the highest trained, professional roofers for our team. We partner with the highest quality shingle manufacturers, and we hand-nail all roofs to ensure quality installation as well. At the end of every project, our supervisor will do an inspection with the homeowner to ensure their satisfaction. At Diamond Construction our mission is to ensure peace of mind for each customer through exceptional service. We work hard to exceed our customers' expectations. Our quality and experience combined with our strong work ethic are only some of the reasons why we maintain an A+ rating on the BBB and Home Advisor - Pro. We are certified by GAF and CertainTeed. 100% Customer Satisfaction Guaranteed. Licensed, Insured, and Accredited Roofers. Convenient Evening & Weekend Appointments. Financing available. Affordable Roofing & Remodeling Quality. New England Premier Roofing Contractor. Additional Email at: office@diamondconstructionma.com

"Did a great Job with roof and helped me with the insurance claim from the storm damage to roof. They are prompt, clean, and super nice. Anything they moved potted plants, my deck furniture , was put back in place with care. They went over yard with a magnet device to get any loose nails , etc that may have fallen in grass. "

Cecile B on October 2025


Avatar for All Under One Roof

All Under One Roof

4.94(
108
)
Approved Pro

All Under One Roof

4.94(
108
)
Approved Pro
Customers say: Quality work
Recommended by 99% of Angi customers
Recommended by 99% of HomeAdvisor customers
14 local quotes requested

Established in 1976, All Under One Roof has the experience and expertise to get the job done right the first time. Our skilled professionals use only the finest tools and materials for your residential or commercial project. We guarantee our work and your satisfaction.

"Overall it went great. John was down quickly after I first contacted him. He came out in person to give me information and confirm the online measurements. Between meeting him, reading the reviews online, and the impeccable warranty I felt very comfortable choosing him (the price was in the middle of the other quotes I got). The whole process took 3 real long days. Obviously it is loud and disruptive while they are working... but you only need a new roof once. I would suggest not parking in your driveway as there are a lot of people and trucks. At the end they cleaned up very nicely. They are a legit roofing company so they pull permits. Overall I am quite please for the job, cost, time etc."

Jason B on May 2024

Established in 1976, All Under One Roof has the experience and expertise to get the job done right the first time. Our skilled professionals use only the finest tools and materials for your residential or commercial project. We guarantee our work and your satisfaction.

"Overall it went great. John was down quickly after I first contacted him. He came out in person to give me information and confirm the online measurements. Between meeting him, reading the reviews online, and the impeccable warranty I felt very comfortable choosing him (the price was in the middle of the other quotes I got). The whole process took 3 real long days. Obviously it is loud and disruptive while they are working... but you only need a new roof once. I would suggest not parking in your driveway as there are a lot of people and trucks. At the end they cleaned up very nicely. They are a legit roofing company so they pull permits. Overall I am quite please for the job, cost, time etc."

Jason B on May 2024


Avatar for TimeproofUSA

TimeproofUSA

New on HomeAdvisorNew on HomeAdvisor
Approved Pro

TimeproofUSA

New on HomeAdvisorNew on HomeAdvisor
Approved Pro
36 local quotes requested
10 years of experience

Here at TimeproofUSA, we're excited to earn your business! Locally owned and operated, we are known in the area for our prompt service and attention to detail. Customer satisfaction is always our primary concern, so be sure to give us a call today!

Here at TimeproofUSA, we're excited to earn your business! Locally owned and operated, we are known in the area for our prompt service and attention to detail. Customer satisfaction is always our primary concern, so be sure to give us a call today!

...
Showing 1-10 of 1046
FAQs for asphalt shingle roofing installation and replacement projects in Winchester, 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 Winchester, 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.