
Get matched with top skylight pros in Winchester, MA
There are 23 highly-rated local skylight pros.
Need a pro for your skylight service project in Winchester, MA?
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Verified Reviews for Skylight Service pros in Winchester, MA
*The Angi rating for Skylight Service companies in Winchester, MA is a rating based on verified reviews from our community of homeowners who have used these pros to meet their Skylight Service needs.
*The HomeAdvisor rating for Skylight Service companies in Winchester, MA is a rating based on verified reviews from our community of homeowners who have used these pros to meet their Skylight Service needs.
Last update on August 21, 2025
Skylight pros in Winchester

Welcome to Ranch Roofing! Our goal is to provide our customers with the highest level of service and satisfaction. Please contact owner Bob O'Sullivan today for friendly, personalized and award winning service. 12 Months no interest, no payment, same as cash (ask for details).
"I wouldn't use any other company. Bob Sullivan, Roy Nagle, and the whole Ranch Roofing crew of professionals have reroofed my Arlington two-family house, fixed storm damage over the years, and just recently replaced the second-floor front and rear porches/roofs. It is beautiful. They are honest, accommodating, top-notch craftspeople, who really go out of their way to be customer focused. From start to finish I felt taken care of and was confident the work would be A+."
Celia D on March 2023
Welcome to Ranch Roofing! Our goal is to provide our customers with the highest level of service and satisfaction. Please contact owner Bob O'Sullivan today for friendly, personalized and award winning service. 12 Months no interest, no payment, same as cash (ask for details).
"I wouldn't use any other company. Bob Sullivan, Roy Nagle, and the whole Ranch Roofing crew of professionals have reroofed my Arlington two-family house, fixed storm damage over the years, and just recently replaced the second-floor front and rear porches/roofs. It is beautiful. They are honest, accommodating, top-notch craftspeople, who really go out of their way to be customer focused. From start to finish I felt taken care of and was confident the work would be A+."
Celia D on March 2023
Start with skylights! At VELUX, our mission is clear: we're dedicated to transforming your space with natural light and fresh air with skylights. Whether you're looking to replace old skylights or install brand-new ones, we will guide you every step of the way. Why Choose VELUX? =================== When it comes to skylights and roof windows, VELUX is the global leader. Here's why you should trust us to transform your home: 1. Innovation and Quality: VELUX skylights are renowned for their innovation and unmatched quality. They're designed to let in abundant natural light while keeping your space leak-free and energy-efficient. 2. Huge Product Selection: You’ll have access to a wide range of skylight options, from fixed to vented skylights. And we are here to help tailor the selection to suit your specific needs and style preferences. 3. Expertise: We take pride in what we do at VELUX, and our team is highly trained to guide you through the entire process. From selecting the perfect product for your space to providing valuable recommendations, we're committed to making sure your skylight project is a complete success. 4. Professional Installation Partners: We don't stop at product selection and recommendations; we also match you with a VELUX-trained installer who will handle the installation of your skylights with precision and expertise.
Start with skylights! At VELUX, our mission is clear: we're dedicated to transforming your space with natural light and fresh air with skylights. Whether you're looking to replace old skylights or install brand-new ones, we will guide you every step of the way. Why Choose VELUX? =================== When it comes to skylights and roof windows, VELUX is the global leader. Here's why you should trust us to transform your home: 1. Innovation and Quality: VELUX skylights are renowned for their innovation and unmatched quality. They're designed to let in abundant natural light while keeping your space leak-free and energy-efficient. 2. Huge Product Selection: You’ll have access to a wide range of skylight options, from fixed to vented skylights. And we are here to help tailor the selection to suit your specific needs and style preferences. 3. Expertise: We take pride in what we do at VELUX, and our team is highly trained to guide you through the entire process. From selecting the perfect product for your space to providing valuable recommendations, we're committed to making sure your skylight project is a complete success. 4. Professional Installation Partners: We don't stop at product selection and recommendations; we also match you with a VELUX-trained installer who will handle the installation of your skylights with precision and expertise.

We are a small, father and son window and door company servicing NH, MA and southern ME. Available for phone calls any day and time and offering our services Monday through Saturday (phone and emails on Sundays as well). We provide high end services at affordable prices and always make sure our customers are satisfied before we leave any job. Please consider using Romeo Vanegas, LLC Custom & Replacement Windows and Doors for your next home improvement project and we look forward to hearing from you.
"He only emailed ask few questions and sent a very high estimate"
Jhony C on August 2020
We are a small, father and son window and door company servicing NH, MA and southern ME. Available for phone calls any day and time and offering our services Monday through Saturday (phone and emails on Sundays as well). We provide high end services at affordable prices and always make sure our customers are satisfied before we leave any job. Please consider using Romeo Vanegas, LLC Custom & Replacement Windows and Doors for your next home improvement project and we look forward to hearing from you.
"He only emailed ask few questions and sent a very high estimate"
Jhony C on August 2020
At Roofer's Edge & Siding, Inc. we have earned a reputation of honesty and professionalism. Whether it's a simple roof repair or a full replacement, we make every effort to ensure our workmanship and customer service is at the high level our customers have come to expect. Our areas of expertise include roofing, siding, windows, doors, insulation, skylights, gutters and leaf guards. We stand behind our workmanship and materials with guarantees that make our customers feel confident in their new investment. With a general contractor license, we are one of the few full-service companies in the area that you can count on for nearly all your home-improvement needs. We know that our reputation is on the line with every job that we do. We have outstanding satisfactory rating with our customers and we are very proud of that.
"I had a terrible experience with Roofers Edges & Siding Inc. We decided to replace the roof for solar system, and hired them to do the job. Remember: you are not hiring Kevin but his crew!!! The communication was extremely poor. At first, despite Kevin agreeing to use an ice shield for the front of my house, his crew was unaware of this requirement. I saw they are using the wrong material, and I had to contact Kevin at the installation day to ensure they were doing the job correctly. It was frustrating that the crew couldn't understand English, and Kevin himself never showed up at my house after the initial estimate. To make matters worse, the roof replacement resulted in a severe water leak problem between my chimney and roof. I asked them to fix it, but they failed once and never showed up again even though they provided an one-year warranty. At very beginning, I fully trusted them, and didn't check regularly, eventually I found the leaking problem persisted several months after the replacement the roof! Despite numerous attempts to contact Kevin, he consistently failed to respond to my calls and texts. Instead, he tried to blame the issue on a chimney problem, and told me they can do a water test, but that never happens. I eventually had to hire a new company to look into it, and they found out that the FLASHING was NOT INSTALLED CORRECTLY!!! and I can see the sky from my attic. I had to pay extra money to redo the flashing job, and Roofers Edges & Siding already lost my trust. The lack of professionalism continued when they claimed to have applied for a permit for the job, and I trusted them. However, several months later, I found out that there was no record of the application with the town. When I contacted them, they said the issue is an incorrect address, how un-professional they are! Overall, I would not recommend Roofers Edges & Siding Inc to anyone. Their poor communication, lack of professionalism, and shoddy workmanship were unacceptable. If you're looking for a reliable and trustworthy roofer, I suggest you look elsewhere."
Boteng Y on May 2023
At Roofer's Edge & Siding, Inc. we have earned a reputation of honesty and professionalism. Whether it's a simple roof repair or a full replacement, we make every effort to ensure our workmanship and customer service is at the high level our customers have come to expect. Our areas of expertise include roofing, siding, windows, doors, insulation, skylights, gutters and leaf guards. We stand behind our workmanship and materials with guarantees that make our customers feel confident in their new investment. With a general contractor license, we are one of the few full-service companies in the area that you can count on for nearly all your home-improvement needs. We know that our reputation is on the line with every job that we do. We have outstanding satisfactory rating with our customers and we are very proud of that.
"I had a terrible experience with Roofers Edges & Siding Inc. We decided to replace the roof for solar system, and hired them to do the job. Remember: you are not hiring Kevin but his crew!!! The communication was extremely poor. At first, despite Kevin agreeing to use an ice shield for the front of my house, his crew was unaware of this requirement. I saw they are using the wrong material, and I had to contact Kevin at the installation day to ensure they were doing the job correctly. It was frustrating that the crew couldn't understand English, and Kevin himself never showed up at my house after the initial estimate. To make matters worse, the roof replacement resulted in a severe water leak problem between my chimney and roof. I asked them to fix it, but they failed once and never showed up again even though they provided an one-year warranty. At very beginning, I fully trusted them, and didn't check regularly, eventually I found the leaking problem persisted several months after the replacement the roof! Despite numerous attempts to contact Kevin, he consistently failed to respond to my calls and texts. Instead, he tried to blame the issue on a chimney problem, and told me they can do a water test, but that never happens. I eventually had to hire a new company to look into it, and they found out that the FLASHING was NOT INSTALLED CORRECTLY!!! and I can see the sky from my attic. I had to pay extra money to redo the flashing job, and Roofers Edges & Siding already lost my trust. The lack of professionalism continued when they claimed to have applied for a permit for the job, and I trusted them. However, several months later, I found out that there was no record of the application with the town. When I contacted them, they said the issue is an incorrect address, how un-professional they are! Overall, I would not recommend Roofers Edges & Siding Inc to anyone. Their poor communication, lack of professionalism, and shoddy workmanship were unacceptable. If you're looking for a reliable and trustworthy roofer, I suggest you look elsewhere."
Boteng Y on May 2023

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.
"This company should not be in business. By far the worst interaction I’ve ever had with a sales person for my entire life. Do not use this company."
John O on September 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.
"This company should not be in business. By far the worst interaction I’ve ever had with a sales person for my entire life. Do not use this company."
John O on September 2024

Thank you for your interest in Phalan Construction! Winner of the Angies List Super Service award 2011, 12, 13, 14, 15 and 2016. Please Contact Me by email at [email protected] or through the contact link at my website www.phalanconstruction.com. Include pictures and a detailed work list for best response. Please understand, I typically work by myself and if I am unable to respond to your email request or phone call within a reasonable time, it is due to prescheduled work. I am interested in your project, and if your to do list is still undone, please re-contact me at a later time. Thanks again, Bob Phalan
"Bob is a true professional! We hired him to replace an old back door and then brought him back to replace a rotted basement window and dryer vent, and then again for a larger project to replace our bulkhead doors and stairs to the basement. He actually built the doors himself because the odd opening size wouldn’t work with any off the shelf solutions. All 3 jobs were challenging due to our home being old and irregular, but Bob was extremely thorough in his evaluation of the conditions and very thoughtful with his recommendations. When unexpected existing conditions came up he communicated them very well to us, along with a plan to address them. We had a budget and Bob worked with us to determine the best approach we could afford. The work itself was very thorough and done with care, we’re sure it will last a long long time. It all looks and operates 100x better. We highly recommend Bob Phalan!"
Kara M on August 2025
Thank you for your interest in Phalan Construction! Winner of the Angies List Super Service award 2011, 12, 13, 14, 15 and 2016. Please Contact Me by email at [email protected] or through the contact link at my website www.phalanconstruction.com. Include pictures and a detailed work list for best response. Please understand, I typically work by myself and if I am unable to respond to your email request or phone call within a reasonable time, it is due to prescheduled work. I am interested in your project, and if your to do list is still undone, please re-contact me at a later time. Thanks again, Bob Phalan
"Bob is a true professional! We hired him to replace an old back door and then brought him back to replace a rotted basement window and dryer vent, and then again for a larger project to replace our bulkhead doors and stairs to the basement. He actually built the doors himself because the odd opening size wouldn’t work with any off the shelf solutions. All 3 jobs were challenging due to our home being old and irregular, but Bob was extremely thorough in his evaluation of the conditions and very thoughtful with his recommendations. When unexpected existing conditions came up he communicated them very well to us, along with a plan to address them. We had a budget and Bob worked with us to determine the best approach we could afford. The work itself was very thorough and done with care, we’re sure it will last a long long time. It all looks and operates 100x better. We highly recommend Bob Phalan!"
Kara M on August 2025

Start with skylights! At VELUX, our mission is clear: we're dedicated to transforming your space with natural light and fresh air with skylights. Whether you're looking to replace old skylights or install brand-new ones, we will guide you every step of the way.
"Kevin from HR Skylights & Sun Tunnels came and fixed it quickly. He's professional and efficient. We could not be more pleased with the work and experience with Kevin."
Josephine H on August 2025
Start with skylights! At VELUX, our mission is clear: we're dedicated to transforming your space with natural light and fresh air with skylights. Whether you're looking to replace old skylights or install brand-new ones, we will guide you every step of the way.
"Kevin from HR Skylights & Sun Tunnels came and fixed it quickly. He's professional and efficient. We could not be more pleased with the work and experience with Kevin."
Josephine H on August 2025

Stratum Construction INC is committed to excellence in every aspect of our business. We uphold a standard of integrity bound by fairness, honesty, and personal responsibility. Our distinction is the quality of service we bring to our customers. Accurate knowledge of our trade combined with ability is what makes us true professionals. Above all, we are watchful of our customers' interests, and make their concerns the basis of our business. https://www.instagram.com/stratum_construction https://www.tiktok.com/@stratumconstruction
"Great work ethic. Job well done at a reasonable price. Will hire them again for future projects."
Sabine J on May 2024
Stratum Construction INC is committed to excellence in every aspect of our business. We uphold a standard of integrity bound by fairness, honesty, and personal responsibility. Our distinction is the quality of service we bring to our customers. Accurate knowledge of our trade combined with ability is what makes us true professionals. Above all, we are watchful of our customers' interests, and make their concerns the basis of our business. https://www.instagram.com/stratum_construction https://www.tiktok.com/@stratumconstruction
"Great work ethic. Job well done at a reasonable price. Will hire them again for future projects."
Sabine J on May 2024
Start with skylights! At VELUX, our mission is clear: we're dedicated to transforming your space with natural light and fresh air with skylights. Whether you're looking to replace old skylights or install brand-new ones, we will guide you every step of the way.
"Excellent customer service and excellent product."
Patti B on January 2025
Start with skylights! At VELUX, our mission is clear: we're dedicated to transforming your space with natural light and fresh air with skylights. Whether you're looking to replace old skylights or install brand-new ones, we will guide you every step of the way.
"Excellent customer service and excellent product."
Patti B on January 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. 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.
"Mighty Dog Roofing did a great job fixing the rake and installing gutters on my house. Work was done in a day, work crew was neat and efficient. "
Karen O 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. 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.
"Mighty Dog Roofing did a great job fixing the rake and installing gutters on my house. Work was done in a day, work crew was neat and efficient. "
Karen O on February 2025
FAQs for skylight service projects in Winchester, MA
In most cases, installing skylights will add to the value of your home, as buyers tend to like the appearance of these windows and prefer houses that let in natural light. However, savvy home buyers who know there are water damage risks with improperly installed skylights will want information on who installed the feature and when. If you can point to a professional skylight installer with experience, then the skylight is more likely to provide a better return on investment.
While it’s possible to install a skylight yourself, we don’t recommend it. DIY window installations are far more likely to leak due to improper placement technique. Making even minor mistakes could lead to thousands of dollars in water damage, meaning hiring a local skylight installer from the start would be more affordable. Plus, working on the roof is dangerous, as is maneuvering heavy, bulky windows up and into place. Even if you’re an experienced DIYer, we strongly recommend hiring a pro to install a skylight.
Skylights are the most likely windows to leak if installed improperly, so there are a few questions you should ask any skylight installer before you hire them:
Do you specialize in skylight installation or only windows in general?
Do you offer any kind of warranty for the installation?
What recourse do I have if the skylight leaks shortly after installation?
Do you have references I can speak with?
How long have you been in business?
Are you licensed and insured?
The average cost to install a skylight is about $1,850, and most homeowners pay between $450 to $5,000 each. Your total price tag will depend on many factors, including the type of roof material, the pitch of your roof, ease of accessibility, the skylight size, and the type of frame and glass you want. You can potentially lower your price if you install multiple windows or skylights simultaneously. Remember to budget $500 to $2,500 for labor costs to complete this project.
Skylights might sometimes increase your homeowners insurance premium, but the increase is usually minimal. Some home insurance companies won’t adjust your premium with the addition of a skylight, so you can contact your insurer or your professional skylight installer to ask about any expected changes. It’s crucial to have an expert install the skylight, as insurance companies may not insure your roof or cover water damage that results from a non-professional skylight installation.





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