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Expert Roofing & Gutter Services in Greater Boston
OLYN Roofing has been a trusted name in the roofing industry for over 50 years, serving homeowners across Greater Boston and MetroWest with unmatched expertise and dedication. Founded in 1974, our company has built a reputation as the Victorian Specialists while expanding our capabilities to address all residential and commercial roofing needs. Our team of highly skilled technicians combines traditional craftsmanship with modern innovations to deliver durable, sustainable solutions tailored to each client's unique requirements. We prioritize eco-friendly materials and energy-efficient systems without compromising affordability, ensuring homeowners receive exceptional value.

With certifications from industry leaders like Owens Corning Platinum Preferred, CertainTeed, and Velux, we maintain the highest standards of quality and workmanship. Our commitment to customer satisfaction is reflected in lifetime craftsmanship warranties, on-site project supervision, and 24/7 emergency services. As a family-owned business, we uphold core values of integrity, transparency, and community responsibility, making us the preferred choice for over 40,000 projects throughout Eastern Massachusetts.
Services
Roof Replacement Gutter Installation Flat Roofing Slate Roofing Roof Cleaning Roof Ice Melt Systems Asphalt Shingles Commercial Roofing Skylight Installation Storm Damage Repair
Details
  • Year established: 1974
Highlights and features
  • 51 years of specialized roofing experience in Greater Boston
  • Family-owned business with on-site project supervision
  • Fully licensed/insured with industry-leading certifications
  • Lifetime craftsmanship warranties on all installations
  • 24/7 emergency services with rapid response times
Associations and certifications
  • Owens Corning Platinum Preferred
  • CertainTeed
  • Velux
What people say
Professional crew Timely completion Quality materials Clear communication Warranty coverage
Services
Roof Replacement
Upgrade aging roofs with premium asphalt shingles, slate, or flat roofing systems designed for durability and energy efficiency. Our expert team handles complete tear-offs and installations for residential and commercial properties, ensuring proper ventilation and water management. Backed by lifetime warranties, our replacements enhance property value while withstanding New England's harsh weather conditions.
Gutter Installation
Custom gutter solutions using aluminum, copper, or fiberglass materials to protect foundations from water damage. We install seamless systems with optional leaf guards and heating elements for winter ice prevention. Our precision measurements ensure optimal water flow while complementing roof aesthetics with multiple color options available.
Roof Ice Melt Systems
Advanced electric heating systems prevent dangerous ice dams on roofs and gutters. Professionally installed cables create continuous drainage paths during winter months, protecting roofing materials and preventing interior water intrusion. Ideal for historic homes and properties with complex rooflines in snow-prone areas.
Commercial Roofing
Durable flat and low-slope roofing solutions for commercial properties using EPDM, TPO, or PVC membranes. Our team provides energy-efficient installations with proper drainage systems, meeting strict building codes and minimizing business disruptions during projects. Maintenance programs extend roof lifespan while controlling long-term costs.
Storm Damage Repair
24/7 response for urgent roof leaks, wind damage, or fallen debris. Certified technicians perform temporary tarping and permanent repairs using insurance-compliant documentation. We work directly with carriers to streamline claims processing while restoring property safety and structural integrity as quickly as possible.
People
Michael Olen
Owner
Third-generation roofing expert with 30+ years of hands-on experience overseeing operations and quality control. Graduated from Wentworth Institute of Technology with construction management degree. Active in local trade associations and community development initiatives.
Linda Olen
President
Business leader with 25 years managing financial operations and customer relations. Implemented company-wide sustainability initiatives reducing material waste by 40%. Holds MBA from Boston University and serves on regional small business advisory boards.
Todd Mellor
General Manager
20-year industry veteran coordinating project timelines and technician training programs. Certified Owens Corning Platinum Preferred contractor with expertise in complex roof designs. Maintains OSHA safety compliance certifications for all field operations.
Jacqie Dent
Head of Production
Project management specialist with 18 years ensuring quality standards across installations. Oversees equipment maintenance and workflow optimization. Holds multiple roofing system certifications and manages vendor partnerships for material procurement.
Shawn O'Connor
Senior Diagnostic Specialist
Roof inspection expert using thermal imaging and moisture detection technology to identify hidden damage. Provides detailed assessment reports for insurance claims and repair planning. Trained in historic preservation techniques for Victorian-era roofing systems.
Questions
What areas do you service?
We serve all of Greater Boston including Bristol, Essex, Middlesex, Norfolk, Plymouth, Suffolk, and Worcester counties with emergency services available 24/7.
Do you offer financing options?
Yes, we provide flexible financing through approved partners to help homeowners manage roofing projects with convenient payment plans.
Are your technicians certified?
All our installers hold manufacturer certifications from Owens Corning, CertainTeed, and Velux, with annual training to maintain technical expertise.
What warranties do you provide?
We offer lifetime craftsmanship warranties on installations plus material-specific manufacturer warranties, with workmanship guarantees on all repair services.
How do I schedule a consultation?
Contact us via phone at 781-769-8599 or through our website form to book a free in-home consultation with a roofing specialist.
Can you handle insurance claims?
Our team assists with insurance documentation and directly negotiates with carriers to ensure proper compensation for storm damage repairs.
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Reviews (4)
Jack Abady
Jun 22, 2022 Report
Called for estimate and response was very quick and professional. The job was completed approximately 3-4 weeks after signing contract. Two men showed up and completed the job in 2 days. They were professional and did excellent work. I would use O'lyn again regarding any roofing issues. Service: Roof repair
Marilyn Dinjian
Jun 08, 2022 Report
We did our research knowing we needed a new roof, but when I read the reviews of O'lyn and met with Roland, We were sold. No hard sells no gimmicks, hard working trusted family business. When work got started we ran into issues on our roof, John, Marco, and Roland were exceptional, they worked with us and made it work. When work was done, and I drove by my house, it looked amazing! Our house roof is the prettiest roof on the street, I am so pleased, so much so we will be doing business with them again. Thank you.
Kenneth Jake Bitner
May 15, 2022 Report
I dreaded replacing the roof, but a leaking skylight made it imperative. O'Lyn was so great to work with. Made the process smooth and painless, and the prices were still good on comparison with other places. They managed to get the whole roof and 4 skylights replaced in one day. And the cleanup was so thorough that our yard looked better than when they first arrived! I know I won't need another roof in my lifetime, but if I did, I would only call O'Lyn.
Weiliang Qiu
May 14, 2022 Report
O'LYN Roofing provided excellent service to replace my house's old roof. When I contacted them, they responded promptly to schedule a meeting with me, through which I was well educated about roof replacement process and roof materials. They did not give me pressure at the end of the meeting so that I could compare their service with other potential service providers. I finally chose O'LYN Roofing because of their professionalism, excellent shingle technology, excellent reputation, and reasonable pricing.

Within a week after I signed the contract with them, they contacted me to schedule roof replacement. During roof replacement, a manager, who is a kind gentlemen, was on-site to answer my questions and supervised the process. The workers are experienced and worked hard. When I went out home, they gave me kind smiles. They put curtains to protect my home when they replaced my house's old roof. As promised, the roof replacement was done within one day.

After finishing the work, they cleaned the surrounding of my house to make sure no nails were left. I am very satisfied with their excellent service and strongly recommend them to anyone who would like to replace their house roofs