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Matthew D’Agostino

Matthew D’Agostino brings years of hands-on roofing experience to O’LYN as a Roof System Specialist. He began his career installing a wide variety of roofing systems before advancing into project management and operations management, where he oversaw roofing installations and ensured an exceptional customer experience. His extensive knowledge of roofing systems allows him to confidently guide homeowners in making the best decisions for their homes.

Originally from Arlington, Massachusetts, Matthew now lives in Rutland. He chose to join O’LYN because of the company’s outstanding reputation for standing behind its work and delivering real value to customers. As a natural leader and problem solver, he enjoys building relationships, understanding customers’ needs, and finding solutions that help them feel confident throughout the roofing process.

When he’s not working, Matthew enjoys spending time at the gym, making memories with his son, and continuously striving to improve himself each day. A fun fact about him? At 200 pounds, he can bench press double his body weight!

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Why Choose O’LYN Roofing?

Trusted Roofers Dedicated to Excellence Since 1974

With decades of experience, O’LYN Roofing has built a reputation for excellence in Greater Boston and MetroWest. You can expect:

  • Live phone answering and in-house customer support
  • Lifetime craftsmanship warranties for long-term confidence in our work
  • On-site project supervisors to ensure every detail is managed
  • Top credentials from Owens Corning Platinum Preferred, CertainTeed, and Velux
  • Full liability and workers' compensation insurance for peace of mind