MHIC# 168718
5 Star Rated
Licensed Bonded and Insured
Insurance Claim Assistance
Workmanship Warranty
We Cover All Of Maryland
Roofing Company Serving Charles County, Maryland
Old School Roofing LLC provides roof repairs, roof replacements, evaluations, siding, and gutter services for homeowners throughout Charles County, Maryland. Whether you’re investigating a leak or planning a new roof, our family-owned team helps you understand your roof’s condition and your options. Based in Southern Maryland, we combine three generations of family construction experience with modern drone inspection technology. Licensed, bonded, and insured — MHIC #168718.
Roofing & Exterior Services in Charles County
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
Communities We Serve in Charles County
Have a roof leak, damaged shingles, or an exterior project you’ve been putting off? Tell us where your Charles County home is located and what work you’re considering. We’ll discuss your concerns and explain the next steps.
All of Maryland
Calvert County
St. Mary’s County
