We Cover All Of Maryland
MHIC# 168718
5 Star Rated
Licensed Bonded and Insured
Insurance Claim Assistance
Workmanship Warranty
5 Star Company
Roofing, Siding & Gutter Services in Maryland
Old School Roofing LLC provides roof replacements, roof repairs, evaluations, maintenance, siding, and gutter services throughout Maryland. Our family-owned company combines construction experience with modern drone inspection technology. Explore our services below or contact us for a free estimate.
Roofing & Exterior Services in Maryland.
Roof Evaluations
Understand your roof’s condition before buying, selling, or planning repairs. We document visible concerns and explain recommended next steps.
Roof Tune Up
Address minor maintenance needs with a roof inspection and recommendations for upkeep and small repairs.
Roof Repairs
Repairs for roof leaks, damaged shingles, and flashing problems. We assess the damage and explain your options.
Full Roof Replacements
Replace an aging or damaged roof with clear material options, a detailed estimate, and cleanup.
Siding
Siding repairs and replacement to protect your home and update its exterior. Get a clear assessment and estimate.
Gutters
Gutter cleaning, repairs, installation, and gutter guards to help manage rainwater around your home.
AI Powered Drone Inspections
Detailed aerial roof photos with AI-assisted analysis to help identify visible concerns and guide further inspection.
What Homeowners Are Saying!
“Pat was very responsive and went above and beyond …”
— Christine Treyes, Google review
“Knowledgeable and experienced professionals …”
— Gavin Santerre, Google review
“Great company to work with. Very professional and caring.”
— Keith Beddow, Google review
“Highly recommend …”
— Hannah Saafir · Facebook recommendation
“… fast and efficient.”
— Jackson Crouse · Facebook recommendation
“… very clean work …”
— Wally Dalrymple · Facebook recommendation
Why Homeowners Trust Old School Roofing
When you hire Old School Roofing, you get a crew that communicates clearly, shows up when we say we will, and keeps you in the loop from the first inspection to the final nail. We’re honest and straightforward about what your roof really needs—no scare tactics, no surprise add‑ons, and no cutting corners just to move on to the next job. Our team protects your property, cleans up thoroughly after every project, and doesn’t consider the work finished until you’re completely satisfied with how your home and yard look when we leave.
Three Generations Family Owned
OSHA 30 Safety Training
30+ Years Construction Experience
Slideshow
Our Roofing Process
Schedule Your Inspection
Schedule a free roof inspection and consultation with our team.
Drone Evaluation & Roof Report
We inspect your roof using advanced drone technology and provide detailed documentation.
Insurance Claim Assistance
If storm damage is present, we'll help document the damage and guide you through the insurance claim process.
Professional Installation
Our team completes your project with quality craftsmanship built to last.
AREAS WE SERVE
All of Maryland
Calvert County
St. Mary’s County
Charles County
Insurance Assistance
Roof Visualizer
See how different shingle colors and roofing styles could look on your home before making a decision. Our roof visualizer helps homeowners confidently choose the right roof while combining modern technology with the trusted craftsmanship of Old School Roofing.
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