MHIC# 168718
5 Star Rated
Licensed Bonded and Insured
Insurance Claim Assistance
Workmanship Warranty
We Cover All Of Maryland
Roofing Company Serving St. Mary’s County, Maryland
From a leaking roof to a planned roof replacement, Old School Roofing LLC helps St. Mary’s County homeowners understand their options and move forward with the work their home needs. Our family-owned company provides roofing, siding, gutter services, and AI-assisted drone roof inspections throughout the county. Based in neighboring Calvert County, we bring three generations of family construction experience to every project. Licensed, bonded, and insured — MHIC #168718.
Roofing & Exterior Services in St. Mary’s 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 St. Mary’s County
We serve homeowners in Leonardtown, Lexington Park, California, Hollywood, Mechanicsville, Charlotte Hall, Great Mills, Callaway, Piney Point, Ridge, Valley Lee, Tall Timbers, Bushwood, Chaptico, Avenue, Coltons Point, and surrounding St. Mary’s County communities.
Our service area extends throughout Maryland. Contact us with your location and project details to discuss availability and scheduling.
All of Maryland
Calvert County
Charles County
