We Cover All Of Maryland
MHIC# 168718
5 Star Rated
Licensed Bonded and Insured
Insurance Claim Assistance
Workmanship Warranty
5 Star Company
Roofing Company Serving Maryland
Old School Roofing LLC is a family-owned roofing company providing roof replacements, roof repairs, inspections, siding, and gutter services throughout Maryland. Based in Calvert County, we combine three generations of family construction experience with modern drone inspection technology. We serve homeowners statewide, with a local focus on Calvert, St. Mary’s, and Charles counties. Contact us for a free estimate. MHIC #168718.
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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 roof maintenance needs before they become larger problems. We inspect your roof and explain recommended maintenance and small repairs.
Roof Repairs
Repairs for roof leaks, damaged shingles, and flashing problems. We assess the damage and explain your repair options.
Full Roof Replacements
Full roof replacement for aging or damaged roofs, with clear material options, detailed estimates, and cleanup.
Siding
Repair damaged siding or replace an aging exterior. We assess your home, explain available options, and provide a clear 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
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.
Insurance Assistance
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
Why Choose Old School Roofing?
Serving homeowners throughout Maryland, Old School Roofing combines proven craftsmanship with modern technology to provide accurate inspections, quality installations, and service you can trust.
Three Generations Family Owned
OSHA 30 Safety Training
30+ Years Construction Experience
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