Benjamin Brothers Roofing & Exteriors 847-533-5505
01/13
Benjamin Brothers Roofing & Exteriors, is a Cary-based contractor with a shop and office in McHenry. Benjamin Brothers provides services across the Chicagoland suburbs into Southern Wisconsin—including Cary, Crystal Lake, Algonquin, McHenry, Barrington, and surrounding communities.

Owners Matt and Cody Benjamin, widely recognized as the Benjamin Brothers, began their journey in the construction trade at an early age, learning alongside their father, who specialized in remodeling and building custom homes. This foundational experience fostered their deep understanding of quality craftsmanship and customer care. Now, as the leading figures behind Benjamin Brothers Roofing & Exteriors, they are fully licensed and insured, offering their expert services throughout northern Illinois and southern Wisconsin.
With over 70 years of combined experience, the Benjamin Brothers excel in exterior remodeling, including roofing, siding, soffit, fascia, gutters, skylights, windows, and doors. They have successfully completed thousands of exterior projects, many involving insurance claims. Their extensive background in handling insurance-related work is why numerous insurance agents often recommend that their clients have the Benjamin Brothers inspect their properties before proceeding with a claim.
For homeowners who have already filed an insurance claim and received an adjuster’s estimate, the Benjamin Brothers provide a detailed review of the paperwork. Insurance documents can be complex, and initial estimates frequently miss necessary items or list incorrect quantities. Their team collaborates closely with homeowners to ensure that nothing is overlooked, guiding them through the process with confidence to achieve the best outcome for their property.
Explore our gallery to see examples of the high-quality work delivered to homeowners who chose Benjamin Brothers Roofing & Exteriors as their trusted exterior contractor.
Whether its doing a free storm damage assessment or providing you with a free estimate to replace your roofing, siding, gutters, or windows, we're here to help!

We install a comprehensive range of roofing systems designed to meet the needs of various building types, architectural styles, and performance requirements. Our expertise includes asphalt shingles, wood shake shingles, composite shingles, metal roofing, and low-slope or flat roofing systems. Each roof is installed using proven methods an
We install a comprehensive range of roofing systems designed to meet the needs of various building types, architectural styles, and performance requirements. Our expertise includes asphalt shingles, wood shake shingles, composite shingles, metal roofing, and low-slope or flat roofing systems. Each roof is installed using proven methods and high-quality materials to ensure long-term durability, weather resistance, and visual appeal.
Our company is fully licensed and insured to complete roofing projects of any size, from single-family residences to large-scale commercial and industrial facilities. Regardless of the scope or complexity of the project, our experienced team is committed to delivering dependable, high-quality roofing solutions that provide lasting protection and peace of mind.

We install a wide range of siding materials to suit your home’s style, durability needs, and budget, including vinyl siding, cedar siding, LP® SmartSide®, and Hardie® fiber cement siding. Each option is installed with careful attention to detail to enhance both curb appeal and long-term performance.
In addition to siding, we offer complete
We install a wide range of siding materials to suit your home’s style, durability needs, and budget, including vinyl siding, cedar siding, LP® SmartSide®, and Hardie® fiber cement siding. Each option is installed with careful attention to detail to enhance both curb appeal and long-term performance.
In addition to siding, we offer complete exterior upgrades such as soffit and fascia replacement, aluminum trim wraps, gutters and downspouts, as well as window and door replacement. By handling every exterior component, we can give your home a cohesive, updated facelift that improves protection, efficiency, and overall appearance—all with one trusted team from start to finish.

We work with all insurance providers and have successfully completed hundreds of insurance-related restoration projects. Our team includes former insurance adjusters, giving us unique insight into the claims process and a strong understanding of how policies, estimates, and scopes of work are written.
Because insurance paperwork can be con
We work with all insurance providers and have successfully completed hundreds of insurance-related restoration projects. Our team includes former insurance adjusters, giving us unique insight into the claims process and a strong understanding of how policies, estimates, and scopes of work are written.
Because insurance paperwork can be confusing, we take the time to review your claim thoroughly and explain everything in clear, straightforward terms. Initial insurance estimates often leave out necessary items or include incorrect quantities, which can impact the quality of repairs if not addressed. By working with our experienced team, you can feel confident that nothing is overlooked and that you receive the full coverage your policy allows.
Benjamin Brothers Roofing & Exteriors
Mailing Address: 16 Lorraine Ct, Oakwood Hills, IL 60013 - Shop Address: 5017 W. Elm St, McHenry, IL 60050
Ph: 847-533-5505 Email: Info@BenjaminBrothers.com