Top-rated roofers.

Get matched with top roofers in Winchester, MA

Enter your zip and get matched with up to 5 pros

Need a pro for your roofing project in Winchester, MA?

Select your specific project to find the pro for you.

TRUSTED BY WINCHESTER, MA HOMEOWNERS

  • Average homeowner rating star icon4.5
    Average homeowner rating
  • Verified reviews icon574
    Verified roofing services reviews

Find Roofers in Winchester

"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
6 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
21 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 Tar Star Roofing

Tar Star Roofing

4.90(
69
)
Approved Pro

Tar Star Roofing

4.90(
69
)
Approved Pro
Customers say: Quality work
Recommended by 91% of Angi customers
Recommended by 91% of HomeAdvisor customers
15 years of experience

Tar Star Roofing is the premier Roofing company serving New Hampshire and Massachusetts for over a decade. Our #1 goal as a company is having complete customer satisfaction and there is no job that is too big or too small. If you want your job done right, call Anthony today !

"Anthony of Tar Star Roofing was referred to me by my real estate agent, and was everything the agent said—honest, reasonably priced, expert, reliable, easy to work with. Tar Star got the job done in no time, and from the photos, the chimney and shingle repairs look amazing! Thank you, Tar Star!!"

Jon C on October 2025

Tar Star Roofing is the premier Roofing company serving New Hampshire and Massachusetts for over a decade. Our #1 goal as a company is having complete customer satisfaction and there is no job that is too big or too small. If you want your job done right, call Anthony today !

"Anthony of Tar Star Roofing was referred to me by my real estate agent, and was everything the agent said—honest, reasonably priced, expert, reliable, easy to work with. Tar Star got the job done in no time, and from the photos, the chimney and shingle repairs look amazing! Thank you, Tar Star!!"

Jon C on October 2025


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
28 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

4.94(
550
)
Approved Pro

Ranch Roofing

4.94(
550
)
Approved Pro
Customers say: Quality work
Recommended by 98% of Angi customers
Recommended by 98% of HomeAdvisor customers
29 years of experience

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).

"We are writing to express our sincere gratitude for the outstanding service we recently received. Ranch Roofing installed our roof back in 2012. Fast forward to 2025, when we had damage to our ridge vent, we called Ranch Roofing, and within 10 minutes had a call back from the owner, Bob. He said he would have it looked at and fixed, but to our surprise, in a matter of a few days, he sent his crew, who ripped the entire ridge vent off and replaced it free of charge. We cannot say enough positive things about Bob, his Crew, and this Company. Thank you Bob- Your quick response and generosity are much appreciated! Sincerely, Maryann and Randy D. "

Maryann D on November 2025

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).

"We are writing to express our sincere gratitude for the outstanding service we recently received. Ranch Roofing installed our roof back in 2012. Fast forward to 2025, when we had damage to our ridge vent, we called Ranch Roofing, and within 10 minutes had a call back from the owner, Bob. He said he would have it looked at and fixed, but to our surprise, in a matter of a few days, he sent his crew, who ripped the entire ridge vent off and replaced it free of charge. We cannot say enough positive things about Bob, his Crew, and this Company. Thank you Bob- Your quick response and generosity are much appreciated! Sincerely, Maryann and Randy D. "

Maryann D on November 2025


Avatar for William Niland Roofing and Carpentry Services

William Niland Roofing and Carpentry Services

4.85(
70
)
Approved Pro

William Niland Roofing and Carpentry Services

4.85(
70
)
Approved Pro
Super Service Award
Customers say: True professional
Recommended by 92% of Angi customers
Recommended by 92% of HomeAdvisor customers
9 years of experience

Welcome to William Niland Roofing and Carpentry Services! 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!

"Bill returned my call and came right away , assessed the roof and repaired it the same day. I would definitely recommend him and use him again in the future."

Janice C on September 2025

Welcome to William Niland Roofing and Carpentry Services! 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!

"Bill returned my call and came right away , assessed the roof and repaired it the same day. I would definitely recommend him and use him again in the future."

Janice C on September 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 Golden Group Construction Corporation

Golden Group Construction Corporation

4.96(
54
)
Approved Pro

Golden Group Construction Corporation

4.96(
54
)
Approved Pro
Customers say: True professional
Recommended by 98% of Angi customers
Recommended by 98% of HomeAdvisor customers
13 years of experience

We’re your award-winning local roofing company specializing in quality roof replacement, roof repairs, home siding replacement, home siding repairs, skylights, Solar Roofing . As a certified roofer, we provide the best roofing systems in Greater Boston and Central Massachusetts. You’ll love your new roof so much, you’ll call us the top local roofing company too! Proud leaders in our community. In the past 10 years, Greta Bajrami and Freddy Campoverde have become roofing industry leaders, catapulting Golden Group Roofing to be a best roofing company in Massachusetts. They did this by insisting on bringing only the best experience to their customers, including: Fully trained and certified year round crew Highest grade roofing, siding and solar materials Complete transparency and excellent customer service Flawless project management from start to finish

"Excellent work"

Jim H on May 2024

We’re your award-winning local roofing company specializing in quality roof replacement, roof repairs, home siding replacement, home siding repairs, skylights, Solar Roofing . As a certified roofer, we provide the best roofing systems in Greater Boston and Central Massachusetts. You’ll love your new roof so much, you’ll call us the top local roofing company too! Proud leaders in our community. In the past 10 years, Greta Bajrami and Freddy Campoverde have become roofing industry leaders, catapulting Golden Group Roofing to be a best roofing company in Massachusetts. They did this by insisting on bringing only the best experience to their customers, including: Fully trained and certified year round crew Highest grade roofing, siding and solar materials Complete transparency and excellent customer service Flawless project management from start to finish

"Excellent work"

Jim H on May 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
33 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

...
Showing 1-10 of 1416
Roofing questions, answered by experts

The size of the dumpster will determine how many squares of shingles can fit in a dumpster. You can place between 4 to 20 squares of shingles in most standard containers.

Stripping existing shingles and installing a new shingle roof takes a professional one to two days, and sometimes up to three days for larger roofs. Additional safety measures necessary for steep roofs can extend the timeframe even further, as do added measures, like replacing roof decking or reinforcing your roof structure to support heavier materials like slate or clay.

Asphalt shingle roofs are more likely to leak than metal roofs because they are more prone to uplift and damage from extreme weather, moss growth, and ice dams. Asphalt shingles also lose shingle grit over time, which decreases their waterproofing qualities. Metal is a more resilient material that will stand up better to strong winds and heavy precipitation, ultimately leading to a lower risk of leaking. As such, metal roofs add to home value with a higher ROI than asphalt roofs in most cases.

A chimney cap costs about $300 on average. The prices range from about $75 to $1,000, depending on the material, size, any repairs needed, and if your chimney cap requires custom fabrication. Chimney caps are usually made from galvanized steel, copper, or stainless steel. Additional costs may include hiring a chimney sweep to clean the chimney before a cap is installed. 

Flapping shingles, or shingles that are lifting or curling away from your roof, can be glued back into place using roofing cement or sealant. Apply the glue underneath the shingle, then press it down firmly. You can leave a brick on top of the shingle to hold it in place overnight while the sealant dries.

The Winchester, 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"