Roofing and Exterior Contracting

O'Brien Home Services has safeguarded homes across Holden, Worcester, and neighboring Massachusetts communities for over 35 years. As one of central Massachusetts's longest-serving roofing contractors, our team brings decades of hands-on experience to each project. Homeowners consistently choose us for complete roof installations and emergency repairs because of our proven track record of quality craftsmanship. Our owner personally supervises every job site, ensuring careful attention to detail and lasting results. Our licensed professionals exclusively use premium CertainTeed and TAMKO brand materials, supported by comprehensive material warranties and our 10-year workmanship guarantee, securing your investment for years to come.

O'Brien Home Services truly stands out because we put customers first. We provide free quotes within 48 hours and remain available 24/7 for emergencies, recognizing that roof problems need prompt attention. Our staff guides you through insurance claims from beginning to end, removing the complexity often associated with this process. We offer special discounts to military personnel, veterans, and first responders as a token of our appreciation. You can also save significantly when combining gutter installation or replacement with your roof replacement. As a local business with deep community ties, we support neighborhood Little League teams—we built their Snack Shack—and regularly donate to local fire departments. Contact us today to request a quote.

Our exterior services cover more than roofing to protect your home's entire structure. We deliver solutions that address all exterior needs while preserving your home's appearance and structural soundness. Our team carefully assesses your property to create customized services that work together with your roofing system for maximum protection.

Our roof installation services reflect our 35+ years of industry knowledge. We install only premium CertainTeed and TAMKO materials, and our installers regularly update their skills through continuing education. Our owner personally oversees each installation, paying close attention to every aspect from beginning to end.

Roof Repairs

Specialized Roofing Services

Our specialized roofing services handle unique architectural challenges and specific homeowner needs. Through our partnership with ABC Supply, we access a wide range of roofing materials suitable for various home styles. Whether you need a full roof replacement, a vapor barrier installed, or moss removed from your roof, we're the ones to call.

Specialty Roof Repairs

Our specialty repair capabilities solve difficult roofing problems requiring advanced methods and knowledge. We successfully fix damaged chimney flashing, pinpoint hard-to-find leaks, and are available after the latest major storm to repair your roof. Our repair specialists have the right training and equipment to work on any roof.