MHIC# 168718
5 Star Rated
Licensed Bonded and Insured
Insurance Claim Assistance
Workmanship Warranty
We Cover All Of Maryland
Roofing, Gutter & Siding Services Across Maryland
Old School Roofing LLC is based in Calvert County and serves homeowners throughout Maryland. We provide roof repairs, full roof replacements, roof evaluations, siding, gutter services, and AI-assisted drone roof inspections. Our local focus includes Calvert, St. Mary’s, and Charles counties, and we welcome inquiries from homeowners elsewhere in Maryland. Contact us to discuss your project and request 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 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
AREAS WE SERVE
Explore our local service pages for Calvert County, St. Mary’s County, and Charles County. These are our primary local areas, but our roofing services extend throughout Maryland. If your town or county isn’t listed below, contact us with your location and project details to confirm availability and scheduling.
Calvert County
St. Mary’s County
Charles County
