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
"I am extremely satisfied with the product and services. The installation was efficient and properly done. I have used this company before for roofing and trust their work."
+45
Serving Chester, MD and surrounding areas
Approved
Super Service Award Winner
In business since 1994
Free estimates
Credit card accepted
"Informative and friendly first meeting, complete with detailed photos of the entire roof and an explanation of the process, followed by 1-day installation of a new roof, with excellent workmanship and a hardworking crew."
+4
Serving Chester, MD and surrounding areas
Approved
In business since 2004
Free estimates
Credit card accepted
"Window & roof insulation quick, easy, & affordable!"
+77
Serving Chester, 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 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
"I am a commercial contractor, and I had a roof emergency which turned into a nightmare,! These guys are great, dependability, integrity, trustworthy, and above all Great workmanship and professionalism. Cannot say enough about Eric, he is a great guy and does what he says and keeps his standards high. I will definitely use them again for other projects and recommend them to anyone looking to cut to the chase and hire a professional contractor at an affordable price."
+12
Serving Chester, MD and surrounding areas
Approved
In business since 2025
Free estimates
Credit card accepted
"AJB Contractors contacted, quoted a price, and emailed the contract for to sign. The next day my roof was repaired. I will definitely use this company for any future home projects. Danny was the point of contact, he was great."
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