4.6 
183 *The Angi rating for Roofing companies in Leonardtown, MD is a rating based on verified reviews from our community of homeowners who have used these pros to meet their Roofing needs.
*The HomeAdvisor rating for Roofing companies in Leonardtown, MD is a rating based on verified reviews from our community of homeowners who have used these pros to meet their Roofing needs.
Last update on June 02, 2026
Serving Leonardtown, MD and surrounding areas
Approved
In business since 2014
Free estimates
Emergency services offered
"I had my roof replaced. The crew was very professional. William kept me up to date. I highly recommend William Richmond, Inc. for all your roofing needs."
+121
Serving Leonardtown, MD and surrounding areas
Approved (Corporate)
Super Service Award Winner
In business since 1994
Free estimates
Credit card accepted
"There's nothing worse that dealing with pooring rain and strong winds and then hearing the drip, drip sound of water coming into your home due to a damaged roof. I reached out to roofing repair companies through Angie's list and Roofing Pups responded. Marcus came out the next day and put my fears at ease. The bad news was that I needed a new roof. He showed me my options available, categorized as "good", "better" and "best". Despite my choosing the lowest option, he still threw in some discounts and upgrades at no additional cost. I signed the contract and he arranged for someone to come out at tarp my roof. He even went the extra mile of going to Home Depot and setting up buckets in my attic to catch the water still coming in. The roofing crew came out two days later and gave me a beautiful new roof. They then meticulously cleaned the area. It was great working with Roofing Pups. I couldn't be happier and highly recommend!"
+4
Serving Leonardtown, MD and surrounding areas
Approved
In business since 1999
Free estimates
Emergency services offered
"Alex is outstanding. The entire experience with Long Roofing is outstanding."
Serving Leonardtown, MD and surrounding areas
Approved
In business since 2004
Free estimates
Credit card accepted
"Roofing repair & replacement, roof came out great!"
+77
Serving Leonardtown, MD and surrounding areas
Approved (Corporate)
Super Service Award Winner
In business since 1992
Free estimates
Warranties offered
"I, initially, had several windows and a door replaced. The installation team did a great job installing the windows and door. I also had Power replace my roof. The roofing team did a great job with that installation as well."
+31
Serving Leonardtown, MD and surrounding areas
Approved
In business since 1998
Free estimates
Emergency services offered
"John Krause Construction recently replaced my roof. I am very pleased with the quality of the work and the price we paid. Their crew was professional and courteous, and a pleasure to work with. They took extra care to clean up my entire yard and ensure I was happy with the job. I would highly recommend this company for any and all home improvement projects."
+113
Serving Leonardtown, MD and surrounding areas
Approved
In business since 2019
Free estimates
Emergency services offered
"Have been working with Roofing solutions for a couple of years on multiple projects. Every project has been finished quickly and smoothly."
+64
Serving Leonardtown, MD and surrounding areas
Approved
In business since 2009
Free estimates
Emergency services offered
"The entire process went very well. The team at JDH is excellent, from their sales guys, to on site managers, to individual workers. All are professional and courteous and take their time to do it right. We've had a few scheduling hic-ups throughout the process, but overall they've been excellent from start to finish. Most importantly, my new roof and skylights look top notch, and will last a lifetime!"
+36
Serving Leonardtown, MD and surrounding areas
Approved
In business since 2008
Free estimates
Credit card accepted
"Roof installation was really quick! Estimate was less than everyone else I received quotes from. I am overall very pleased with the whole process."
Serving Leonardtown, MD and surrounding areas
Approved
Super Service Award Winner
In business since 2011
Free estimates
Emergency services offered
"Brian Shenk was very professional and helpful through the process of replacing our roof. When we had questions he called us back in a timely manner. Project timing was on point. The quality of the roof was good.. Very pleased with the new roof!"
+21
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