A new roof or a major repair is one of the bigger checks a homeowner writes, and the contractor you pick matters just as much as the shingles you choose. Southern Maryland has no shortage of roofing companies, from established local crews to out-of-area outfits that show up after a big storm and are gone before the warranty means anything. Here are seven questions worth asking before you sign anything, and why each one matters.
1. Are You Licensed and Insured in Maryland?
This is the question to ask first, and the one some contractors would rather you did not. Ask for the actual license number and check it, do not just take a verbal yes. Maryland’s Department of Labor runs a free public license lookup where you can confirm a contractor’s registration status in about two minutes. Ask specifically about liability insurance and workers’ compensation as well. If a worker is hurt on your roof and the contractor has no workers’ comp, the liability can land on the homeowner, not the company.
2. How Long Have You Been Roofing in This Area?
Years in business matters less than years working in your specific area. A company that has been roofing Southern Maryland homes for a decade knows the local building codes, the weather this region actually gets, and the housing stock, older colonials, capes, and split levels included. A company that just opened a temporary office after a storm rolled through may be gone before your shingles are.
3. Can You Provide Local References or Reviews?
Ask for addresses or neighborhoods, not just names, and if possible drive by a completed job. Reviews on Google, the Better Business Bureau, and Yelp matter, but read a handful rather than just the star rating. A contractor with 40 reviews and a few honest, specific complaints they responded to well often tells you more than one with five generic five-star reviews and nothing else.

4. What Manufacturer Certifications Do You Hold?
Manufacturers like GAF certify contractors who meet training and volume requirements, and certified installers can usually offer stronger, longer manufacturer warranties than an uncertified crew installing the same shingle. It also tells you the contractor installs enough roofs to keep that certification current, rather than roofing as a side business.
5. Will I Get a Written, Detailed Estimate?
A real estimate names the materials, the scope of work, the timeline, and the total cost in writing, not a verbal number over the phone. Be cautious of a quote that arrives suspiciously fast without the contractor ever getting on your roof, and just as cautious of pressure to sign the same day for a discount. A legitimate contractor’s price does not usually expire by dinnertime.
6. Who Actually Does the Work, Your Crew or a Subcontractor?
Some companies sell the job and then hand it to a subcontracted crew you never meet or vet. That is not automatically a problem, but you deserve to know it upfront, along with who is actually accountable if something goes wrong during or after the install. Ask directly whether the crew on your roof works for the company you are signing with.

7. What Does Your Warranty Actually Cover?
A roof usually carries two separate warranties: one on the materials from the manufacturer, and one on the workmanship from the contractor who installed it. Ask how long the workmanship warranty runs, what specifically voids it, and what happens if the company is not around in ten years. A five-year workmanship warranty from a company that has been in business two years is worth asking harder questions about.
Finding the Right Fit in Southern Maryland
None of these seven questions are complicated, and a legitimate local contractor will not hesitate to answer any of them clearly. The homeowners who end up unhappy with a roofing job are usually the ones who skipped this part and went with whoever showed up first or quoted the lowest number. Take the extra day to ask.
One Vision Roofing is a licensed, insured, GAF Certified roofing contractor based in Mechanicsville, serving Hughesville, Charlotte Hall, Leonardtown, and the wider Southern Maryland region. Contact us today for a free estimate, or call (301) 909-3383.