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Roofing in Boston, MA

Boston’s harsh winters and hot, humid summers take a toll on roofs. From heavy snowfall and ice dams to intense heat and thunderstorms, the area’s extreme weather conditions necessitate durable, well-installed roofing systems. O’LYN Roofing has been the leading Boston roofing contractor for over 50 years, providing expert roof installations, repairs, and replacements customized for the region’s climate. Our team specializes in high-quality asphalt shingles, flat roofing membranes, slate, and more to protect homes and businesses throughout Greater Boston against nature’s harshest elements year-round.

Boston Roofing Services

O’LYN Roofing offers comprehensive roof services for residential and commercial properties across Boston and the surrounding areas. Our knowledgeable roofing professionals thoroughly assess each client’s unique needs and provide tailored solutions. From complete replacements to repairs, maintenance, and upgrades, we have the experience and knowledge to handle any roofing project seamlessly. Whether you need minor fixes or a total roof overhaul, you can count on our roofing contractors for quality workmanship and materials.

Has your roof sustained significant damage or simply reached the end of its lifespan? We provide complete roof replacement services, ensuring your property is fully protected for years to come. Our skilled team carefully removes the old roofing materials, inspects the roof deck for any underlying issues, and reinforces it as needed before installing a brand new, long-lasting roofing system using premium products from top manufacturers.

Increase natural light and enhance the beauty of your home or business with our skylight and daylight installation services. These architectural features drastically improve interior ambiance while potentially reducing energy costs by utilizing the sun’s rays. We install and integrate high-quality skylights and daylights from trusted brands, optimizing performance and aesthetics. Our team has the specialized expertise required to seamlessly incorporate these roof elements while maintaining structural integrity for waterproof, leak-free operation.

Ice dams and heavy icicle buildup can wreak havoc on roofs during Boston’s harsh winters, potentially causing costly water damage and interior leaks. Our ice melt systems are installed along the edges of your roof to prevent hazardous ice accumulation before it starts. This proactive solution keeps roofs clear and allows them to continue functioning properly all winter long. We offer professional installation and ongoing maintenance for effective, reliable ice dam prevention year after year.

Gutters and downspout systems protect your home from water damage by directing rainfall away from the foundation. Without a well-functioning drainage system, heavy rains can lead to basement flooding, soil erosion around the landscape, and other moisture-related issues. Our team installs new, seamless aluminum gutters with durable aluminum downspout systems or repairs existing gutters to restore proper water flow. We also provide thorough gutter cleaning to remove clogs and debris.

Roofing Types

At O’LYN Roofing, we install and repair an extensive array of roofing types. Our experienced team guides you through the selection process to find the ideal roofing material to meet your needs and budget while complementing your property’s architectural style. We work exclusively with premium products from respected manufacturers to ensure long-lasting durability and performance.

Asphalt shingle roofing remains one of Boston’s most popular and economical roofing choices for homes, thanks to its versatility, easy maintenance, and aesthetic appeal. At O’LYN Roofing, we offer a wide selection of colors, styles, and efficiency ratings from top brands like GAF, CertainTeed, and Owens Corning. Our certified installers ensure proper underlayment, ice and water barriers, flashing details, and fastening for a secure fit that withstands the area’s punishing weather extremes. Asphalt shingles deliver reliable protection and beauty that complements any home’s architecture.

Flat roofing systems are ideal for many commercial buildings as well as some residential triple-decker properties like condos and apartments across Boston. O’LYN Roofing specializes in installing and maintaining a wide range of premium flat roofing materials. Our extensively trained roofers have expertise in the unique application techniques required for the proper installation and longevity of flat roof systems on large, open expanses to prevent leaks, UV damage, and premature failure.

For historic New England homes, upscale properties, and buildings with classic architectural styles, genuine slate roofing provides unparalleled elegance and durability. O’LYN Roofing has decades of experience installing, repairing, and maintaining these iconic slate roofs across Greater Boston. Real slate offers superior fire resistance and can last over a century with proper care. Our craftsmen are highly skilled in ensuring precise cuts, flashing details, and leak-proof installation for optimal slate roof performance.

Boston Roof Financing Options

While investing in quality roofing provides excellent long-term value and protection for your property, upfront costs can be daunting. That’s why O’LYN Roofing aims to make our premium products and services more accessible with flexible roof financing options through third-party lenders. We’ve partnered with top financial institutions to offer convenient monthly payment plans tailored to your budget. These plans allow you to get the new roof your home needs now and pay over time in manageable installments rather than postponing the project. Financing is available for full roof replacements as well as repairs, upgrades, and installations.

Aerial view of a large residential home with gray shingle roofing surrounded by lush greenery and a well-manicured lawn.
Drone shot of a two-story house with complex gray shingle roofing, featuring multiple skylights and surrounded by dense trees and landscaped yard.

Owens Corning Platinum Preferred Contractor

When you choose O’LYN Roofing for your Boston area project, you can have complete confidence in the skills and professionalism of our team. We take tremendous pride in being designated an Owens Corning Platinum Preferred Contractor – an elite distinction only offered to the top 1% of roofing companies nationwide after rigorous vetting and on-site inspections. This highly coveted accreditation recognizes our exemplary workmanship, superior product knowledge, commitment to ongoing training and certifications, use of full Owens Corning roofing systems with enhanced warranties, and overall dedication to professional excellence. 

Roof Replacement Gallery

View our portfolio of completed roofing projects on homes throughout the Watertown area. Our roofing gallery showcases the quality craftsmanship and beautiful results you can expect from O’LYN Roofing. Browse images of new roof installations, skylight additions, ice melt systems, and more to gain inspiration for your home improvement project. You’ll see firsthand how our team’s attention to detail and commitment to using premium materials results in stunning, long-lasting roofs that increase curb appeal and property value. Our gallery is a testament to the pride we take in our work and our dedication to exceeding customer expectations on every job.

Roofing Reviews

Our 50+ years serving homeowners and businesses have earned us a sterling reputation for exceptional service, quality craftsmanship, and commitment to our customers’ complete satisfaction. Many enthusiastic reviews reflect this dedication, with clients praising our skilled workmanship, knowledgeable crews, timely and efficient service, and meticulous attention to detail on every job. As a local, family-owned company, we treat each client’s home as we would treat our own, ensuring the roofing process is as seamless and stress-free as possible from start to finish. We maintain open communication throughout projects and stand behind our work with robust warranties.

Contact O’LYN Roofing For Boston Roofing Services

When it comes to safeguarding your greatest investment against the harsh New England elements, don’t settle for less than the best. Choose O’LYN Roofing, Boston’s premier roofing contractor, for craftsmanship, expertise, and stellar customer service you can depend on. Our team specializes in installing, repairing, and maintaining roofing systems using premium materials from respected brands, delivering long-lasting value tailored to the area’s unique climate challenges. With detailed inspections, precise workmanship, and exceptional product knowledge honed over decades of experience, we guarantee that every roofing project meets the highest standards of quality and your complete satisfaction.Contact us today at (781) 300-7231 or complete our online form to schedule your free roof evaluation and estimate from Boston’s most trusted roofing professionals.

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