Get matched with top roofers in Winchester, MA
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563 Verified Reviews for Roofing pros in Winchester, MA
*The Angi rating for Roofing companies in Winchester, MA is a rating based on verified reviews from our community of homeowners who have used these pros to meet their Roofing needs.
*The HomeAdvisor rating for Roofing companies in Winchester, MA is a rating based on verified reviews from our community of homeowners who have used these pros to meet their Roofing needs.
Last update on May 22, 2025
Roofers in Winchester
Most people stress over home improvements. We make it easy and affordable. The exterior home experts at Couto Construction have been beautifying homes across Southeastern Massachusetts, Cape Cod and Rhode Island for more than 30 years. We've helped thousands of homeowners, and we're here for you.
Most people stress over home improvements. We make it easy and affordable. The exterior home experts at Couto Construction have been beautifying homes across Southeastern Massachusetts, Cape Cod and Rhode Island for more than 30 years. We've helped thousands of homeowners, and we're here for you.
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. At Mighty Dog Roofing, we pledge superior service to our customers through excellent communication and customer service. How do we accomplish that? Courteous customer education, community service, and the highest level of integrity and ethics. 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.
"Reliable, Professional, and Efficient! We couldn’t be happier with the snow and ice dam removal service from Mighty Dog! They responded to my last minute request quickly, arrived right on time, and handled everything with great care. The team was professional, friendly, and made sure to remove the ice safely without damaging the roof. It’s clear the crew knew what they’re doing, and their attention to detail gave us peace of mind eliminating snow and ice dams. I highly recommend them to anyone needing snow or ice dam removal—fantastic service from start to finish!"
Tiffany S on February 2025
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. At Mighty Dog Roofing, we pledge superior service to our customers through excellent communication and customer service. How do we accomplish that? Courteous customer education, community service, and the highest level of integrity and ethics. 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.
"Reliable, Professional, and Efficient! We couldn’t be happier with the snow and ice dam removal service from Mighty Dog! They responded to my last minute request quickly, arrived right on time, and handled everything with great care. The team was professional, friendly, and made sure to remove the ice safely without damaging the roof. It’s clear the crew knew what they’re doing, and their attention to detail gave us peace of mind eliminating snow and ice dams. I highly recommend them to anyone needing snow or ice dam removal—fantastic service from start to finish!"
Tiffany S on February 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!
"Service went excellent . Jack and Mike King did a wonderful job, they were pleasant and was reasonable. I would recommend them to anybody. They knew their job ,they knew their work, and I would call them in the future. I would give them a 10 star if I could."
Linda G on March 2023
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!
"Service went excellent . Jack and Mike King did a wonderful job, they were pleasant and was reasonable. I would recommend them to anybody. They knew their job ,they knew their work, and I would call them in the future. I would give them a 10 star if I could."
Linda G on March 2023
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: [email protected]
"Good job. Quick and professional"
Scott C on July 2024
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: [email protected]
"Good job. Quick and professional"
Scott C on July 2024
As a commercial and residential general contracting company with 24 years of experience, offering fiber cement siding, vinyl siding, wood shake siding. Roofing; shingle, flat , slate, metal. Carpentry, framing, finish carpentry, chimney, masonry, repairs and more, we take pride in our projects and guarantee fast, reliable, and high quality service. Our company is fully licensed, and OSHA certified. We do replacement, new installation, and roof repairs. Please contact us and get a quote for your next job.
"Had them do a ton of great work on my house! Roof, siding, deck, redesign front entry, chimney, stairs, walkway. Basically rebuilt the outside of my home!! A+ work! Super professional and courteous to deal with. Quickly answered all my inquiries. They do superior work at an extremely fair price. I would recommend them to anyone👍"
Evan K on October 2024
As a commercial and residential general contracting company with 24 years of experience, offering fiber cement siding, vinyl siding, wood shake siding. Roofing; shingle, flat , slate, metal. Carpentry, framing, finish carpentry, chimney, masonry, repairs and more, we take pride in our projects and guarantee fast, reliable, and high quality service. Our company is fully licensed, and OSHA certified. We do replacement, new installation, and roof repairs. Please contact us and get a quote for your next job.
"Had them do a ton of great work on my house! Roof, siding, deck, redesign front entry, chimney, stairs, walkway. Basically rebuilt the outside of my home!! A+ work! Super professional and courteous to deal with. Quickly answered all my inquiries. They do superior work at an extremely fair price. I would recommend them to anyone👍"
Evan K on October 2024
Did you know that it's unwise to spend too much but it's worse to spend too little? How do you choose the right contractor? First, they should listen to what you want to have done, then they should take a look at what needs to be done. Our certified expert will provide a full inspection of the problem areas. We will take digital photos of these areas, and provide a complete color coded plan so that you can see what we saw. IN EXCHANGE FOR OUR TIME AND EFFORTS, ALL THAT WE ASK IN RETURN IS THAT ANYONE WHO WOULD HAVE INPUT BE PRESENT TO DISCUSS YOUR OPTIONS. We believe that this approach provides everyone with the best way to make a good informed decision. If you agree, please call us now. You'll be glad you did! Since 1969, GF Sprague has worked with discerning homeowners who buy the right job at the right price.
"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
Did you know that it's unwise to spend too much but it's worse to spend too little? How do you choose the right contractor? First, they should listen to what you want to have done, then they should take a look at what needs to be done. Our certified expert will provide a full inspection of the problem areas. We will take digital photos of these areas, and provide a complete color coded plan so that you can see what we saw. IN EXCHANGE FOR OUR TIME AND EFFORTS, ALL THAT WE ASK IN RETURN IS THAT ANYONE WHO WOULD HAVE INPUT BE PRESENT TO DISCUSS YOUR OPTIONS. We believe that this approach provides everyone with the best way to make a good informed decision. If you agree, please call us now. You'll be glad you did! Since 1969, GF Sprague has worked with discerning homeowners who buy the right job at the right price.
"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
Capital Construction was founded in 2005. We are an award-winning exterior contracting specialist. We specialize in roofing, siding, windows, and doors, and pride ourselves on fantastic customer service and top-notch craftsmanship. We hold numerous certifications in the industry, and we are proud to work with the best products from leading manufacturers. No matter what home improvement needs you have, Capital is here to provide you with quality solutions. Our mission is simple: to improve the lives of our customers by providing the highest quality building materials installed by highly skilled, professionally trained craftspersons with the highest level of customer service.
"We had Capital Construction replace the siding, windows, and doors at our house. Their work is low quality. Windows were not completely fastened, casing was a hack job, and our door sweep after 1.5 years of use is falling apart. I would not recommend hiring Capital Construction for any project."
Sean S on January 2025
Capital Construction was founded in 2005. We are an award-winning exterior contracting specialist. We specialize in roofing, siding, windows, and doors, and pride ourselves on fantastic customer service and top-notch craftsmanship. We hold numerous certifications in the industry, and we are proud to work with the best products from leading manufacturers. No matter what home improvement needs you have, Capital is here to provide you with quality solutions. Our mission is simple: to improve the lives of our customers by providing the highest quality building materials installed by highly skilled, professionally trained craftspersons with the highest level of customer service.
"We had Capital Construction replace the siding, windows, and doors at our house. Their work is low quality. Windows were not completely fastened, casing was a hack job, and our door sweep after 1.5 years of use is falling apart. I would not recommend hiring Capital Construction for any project."
Sean S on January 2025
When you choose Klaus Larsen LLC, you select a company of professionals who take great pride in our craftsmanship, and treat you, your time, and your property with the utmost respect. We make sure that before we leave your home, you are completely satisfied with our work and our cleanup, and we consider you a customer for as long as our warranty lasts. And that’s a lifetime! Klaus Larsen LLC serves Connecticut and Rhode Island with roofing services such as roof replacement, roof repair, gutters, attic insulation, and more. Put a Klaus on Your House! Call us for a free, no-obligation estimate today! About Klaus Larsen: Klaus Larsen bought his first apartment building in Denmark at the age of 21, renovating every single one of the 13 apartments in it in less than three years. At the age of 32, he immigrated to the US with his tools and $300 in his pocket to live the American Dream. Little did he know those metric tools would do him little good in a country that only used inches and feet. By 1998 he was able to start his own home improvement business, becoming a roofing-only company in 2010. Klaus is well known for his historic work, using his ingenious creativity to update antique homes so their roofs perform properly while maintaining their architectural integrity. His attention to detail and Old World craftsmanship have earned him a reputation for helping to maintain New England’s rich history while integrating state-of-the-art roofing technology into it’s homes.
When you choose Klaus Larsen LLC, you select a company of professionals who take great pride in our craftsmanship, and treat you, your time, and your property with the utmost respect. We make sure that before we leave your home, you are completely satisfied with our work and our cleanup, and we consider you a customer for as long as our warranty lasts. And that’s a lifetime! Klaus Larsen LLC serves Connecticut and Rhode Island with roofing services such as roof replacement, roof repair, gutters, attic insulation, and more. Put a Klaus on Your House! Call us for a free, no-obligation estimate today! About Klaus Larsen: Klaus Larsen bought his first apartment building in Denmark at the age of 21, renovating every single one of the 13 apartments in it in less than three years. At the age of 32, he immigrated to the US with his tools and $300 in his pocket to live the American Dream. Little did he know those metric tools would do him little good in a country that only used inches and feet. By 1998 he was able to start his own home improvement business, becoming a roofing-only company in 2010. Klaus is well known for his historic work, using his ingenious creativity to update antique homes so their roofs perform properly while maintaining their architectural integrity. His attention to detail and Old World craftsmanship have earned him a reputation for helping to maintain New England’s rich history while integrating state-of-the-art roofing technology into it’s homes.
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.
"One of the worst companies I have EVER dealt with in my life. Nothing but runaround, lies, and lack of accountability. They will tell you something over the phone, then when you follow-up, they will magically lose all records of prior conversations. I was told replacement windows would be ordered in June 2024 - never ordered. In January, ordered correctly with 4-6 week expedited delivery time quoted. Now in Feb, was told the windows would not be ready until end of March (total of nearly 11 weeks since order). Magically, they have no record of quoting me 4-6 weeks, though I have email records saying otherwise. Just a miserable company to do business with, would never recommend to any homeowner."
Shankha M on February 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.
"One of the worst companies I have EVER dealt with in my life. Nothing but runaround, lies, and lack of accountability. They will tell you something over the phone, then when you follow-up, they will magically lose all records of prior conversations. I was told replacement windows would be ordered in June 2024 - never ordered. In January, ordered correctly with 4-6 week expedited delivery time quoted. Now in Feb, was told the windows would not be ready until end of March (total of nearly 11 weeks since order). Magically, they have no record of quoting me 4-6 weeks, though I have email records saying otherwise. Just a miserable company to do business with, would never recommend to any homeowner."
Shankha M on February 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.
"Jason and Liz are incredibly accommodating, super friendly and extremely knowledgeable on all roofing related matters~ they take the time to explain everything no matter how many questions you may have (and we had a lot) and provide pictures both before and after so you can actually see the amazing quality of their work~ their prices are very fair and reasonable and we would highly recommend them and give them an A+++++ across the board!!!"
Rachel S on May 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.
"Jason and Liz are incredibly accommodating, super friendly and extremely knowledgeable on all roofing related matters~ they take the time to explain everything no matter how many questions you may have (and we had a lot) and provide pictures both before and after so you can actually see the amazing quality of their work~ their prices are very fair and reasonable and we would highly recommend them and give them an A+++++ across the board!!!"
Rachel S on May 2025
Typical roofing repairs cost between $380 and $1,800 on average. However, most homeowners spend approximately $1,100 on a roofing repair project. The size of the roof, the extent of the damage, and the type of project all impact the final cost. External factors like product availability and supply chain issues may also affect the price.
Projects like repairing damaged gutters will only be around $180 to $560, whereas repairing a sagging roof will be a higher expense at $1,500 to $7,000.
Roof repairs start at around $700.00 and go up from there. There are many significant factors that come into play, and each customer's needs will rarely be the same.
The cost to replace your roof is often significantly more expensive than the cost to repair it. On average, homeowners will spend between $5,890 and $12,800 to replace a roof. The size of the roof, the roof’s pitch, and the number of stories the house has will significantly affect the overall cost. You can expect to spend upwards of $46,000 for large, high-end roofs.
This all depends upon size, type and complexity of the actual sloped areas of the roof. An accurate estimate with detailed lists of covered and additional items is imperative when purchasing and protecting yourself during the process.
Although not every state issues licenses for roofing pros, it's important to check with your county or city if hiring a licensed roofing contractor is necessary. Hiring an unlicensed roofer might result in low-quality work and potential legal issues if an accident happens. It’s always best to check the qualifications and licenses of your roofer before they begin a project.
As you browse our pro listings, take note of the “Angi Approved” badge. Angi Approved businesses meet our standards for certification which include:
The owner, principal, or relevant manager passed a criminal background check
Required to have applicable state and local licenses
Maintain an average star rating of 3.0 or better on our network, if they have at least one review
Paying to advertise their services
Meeting any other eligibility criteria required by Angi
Keep in mind licensing is different from certifications. A license is a legal requirement to operate a business, while certifications are voluntary.
Before hiring a roofing contractor to work on your project, there are a few things you will want to ask, including:
Do you use roofing subcontractors?
Do you offer a warranty?
Do you have any references?
How will you clean up after the project is complete?
Will you remove my old or damaged roof?
How long have your crews been working with you?
Do you offer a warranty?
Do you have any references?
How will you clean up after the project is complete?
Will you remove my old or damaged roof?
Roofing is a highly skilled and labor-intensive trade. Because of this, you can expect to pay an average of $2 per square foot for your roofing professional. Roofing labor costs generally make up about 60% of the overall project cost.
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