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
In business since 1999
Free estimates
Emergency services offered
"Our company contact Aaron was patient, professional and took the time to educate us about roof components and their installation."
Serving Leonardtown, MD and surrounding areas
Approved
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 2004
Free estimates
Credit card accepted
"Window & roof insulation quick, easy, & affordable!"
+77
Serving Leonardtown, MD and surrounding areas
Approved (Corporate)
Super Service Award Winner
In business since 1992
Free estimates
Warranties offered
"Excellent!!! Great work !!! They have done 2 big jobs for us (roof & windows); we were happy with both results."
+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
At JDH Remodeling, we specialize in enhancing and protecting your home with a comprehensive range of services. As expert roofing contractors, we ensure your roof is robust and reliable. Our gutter services are designed to effectively manage water flow, preventing damage to your home. We also offer siding solutions that not only add aesthetic appeal but also provide essential protection against the elements. Our insulation services improve energy efficiency, enhancing comfort and reducing costs. Additionally, our window installation services bring natural light and style into your home while ensuring durability and performance. Trust JDH Remodeling for quality craftsmanship and exceptional service.
+36
Serving Leonardtown, MD and surrounding areas
Approved
In business since 2008
Free estimates
Credit card accepted
"Very pleased with St. Mary's Roofing"
Serving Leonardtown, MD and surrounding areas
Approved
Super Service Award Winner
In business since 2011
Free estimates
Emergency services offered
"Sam stopped by my house one day and mentioned that there was an issue with my roof and that Priceless Home Improvement would help be with the entire process to replace it at no cost to me. At this time, I had so many other obligations going on that did not have the time or energy to take on another thing. He was so persusaive that I went ahead that signed up to have the roof replaced. Priceless took it from there. They handled everything from meeting the inspector from the insurance company to the final replacement of the roof. the work was outstanding and this whole process was painless with Priceless Home Improvement. I would recommend Sam and Priceless Home Improvement to anyone interested in going with a reliable company to replace their roof."
+21
From average costs to expert advice, get all the answers you need to get your job done.
A new roof improves curb appeal, increases home value and keeps your living space protected from the elements. Learn about average roof replacement costs to set your budget.
The average cost of roof repair for U.S. homeowners averages between $386 and $1,875. Learn what factors can affect roof repair costs.
Wondering about the cost to tarp a roof after a large storm or before a major roof renovation? We'll break it down by size, style, and scenario.
All of the parts of your roof work together to protect your home. Learn the anatomy of a roof and how each part functions.
Roof leaks are an emergency, so knowing who can tarp your roof quickly and correctly can save you from major water damage if you ever experience a leak.
Using a roof replacement checklist ensures you get the key tasks accomplished.
