4.6 
672 *The Angi rating for Roofing companies in Chester, 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 Chester, 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 October 30, 2025
Serving Chester, MD and surrounding areas
Approved
In business since 1987
Free estimates
Warranties offered
"Great. They were able to do the same week we called. Looks very nice and matches roof on home"
+45
Serving Chester, MD and surrounding areas
Approved (Corporate)
Super Service Award Winner
In business since 1994
Free estimates
Credit card accepted
"We had a really good experience with Roofing Pups. Their rep Alex was great to work with, and the roofing crew that came to our house did a good job and cleaned up afterward. We opted to get our gutters replaced as well as our roof, which required a second day of work. The Roofing Pups employee in charge of this job (also named Alex) noticed that the color of the new gutters didnt match our house, and made a point of checking it with us before getting started. We really appreciated this as the new gutters would have clashed with the color of our siding! Everyone with the company was great about making the change, ordering new parts and rescheduling the job. We were very impressed with their service and professionalism. We would definitely use Roofing Pups again!"
+4
Serving Chester, MD and surrounding areas
Approved
Super Service Award Winner
In business since 2004
Free estimates
Emergency services offered
"Very pleased with my new roof! ð"
+73
Serving Chester, MD and surrounding areas
Approved (Corporate)
Super Service Award Winner
In business since 1992
Free estimates
Warranties offered
"We are having our roof and gutters replaced currently and have had a great experience so far! From the sales intro w/ Christian, to the crew doing the work, and QA follow-up w/ Alex, all of the steps have gone smoothly and the staff has been very knowledgeable and helpful."
+31
Serving Chester, MD and surrounding areas
Approved
In business since 2002
Free estimates
Warranties offered
"From beginning to the very end, AWESOME! On time for the estimate and on time for the scheduled installation day. Every membership the staff was friendly, knowledgeable, patient with all with questions. The roof replacement was done quickly and cleanup was thorough. We are very happy."
+9
Serving Chester, 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 Chester, 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 Chester, MD and surrounding areas
Approved
Super Service Award Winner
In business since 2009
Free estimates
Emergency services offered
"Casey and his crew have been my go-to team over the last 10years and on several projects, from complete rehabs from roofing. soffits and fascia, outside, to the new kitchen and baths inside! My wife especially LOVES the screened -in porch they added on to our family home, and she's fussy about the quality of work to say the least. They have traveled far and wide across the Eastern Shore and even rehabbed a rental for me in Dover! Good work is hard to find nowadays, but Casey and crew clean up after themselves daily, and most importantly are REASONABLE in their rates !"
Serving Chester, MD and surrounding areas
Approved
In business since 2018
Free estimates
Credit card accepted
"The crew showed up on time, worked quietly and efficiently and left the area better than it was. Our new roof is beautiful and expertly installed. Erick is fair and honest . Pricing was competitive. I would trust him with any other work I might need."
+12
Serving Chester, MD and surrounding areas
Approved
In business since 2025
Free estimates
Credit card accepted
We invite you to experience a tradition of customer satisfaction that will exceed your greatest expectations. Our professionalism and quality workmanship will accurately reflect your taste and lifestyle. From conception to completion, we work with you until the job is done. We are ethical, honest, and easy to communicate with.\n\nCall us today you'll be pleased you did. Thank you\n\n
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