4.5 
125 *The Angi rating for Roofing companies in Chestertown, 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 Chestertown, 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 July 04, 2025
Serving Chestertown, 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 Chestertown, MD and surrounding areas
Approved (Corporate)
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 Chestertown, MD and surrounding areas
Approved
In business since 2004
Free estimates
Credit card accepted
"Window & roof insulation quick, easy, & affordable!"
+77
Serving Chestertown, 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 Chestertown, MD and surrounding areas
Approved
In business since 2002
Free estimates
Warranties offered
"Pete and his team did an outstanding job from the moment they arrived until the final clean-up. What a hard working team! Pete did a great job communicating with me prior to the job and updating me throughout the day during the job. We love our new roof and the quality job! We were impressed with the clean up...not a single piece of trash was left behind!! I would highly recommend Pete and his team for any roofing job and would be pleased to serve as a reference to any potential future clients of Spicer Brothers."
+9
Serving Chestertown, 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 Chestertown, MD and surrounding areas
Approved
In business since 2023
Free estimates
Credit card accepted
New Castle Constructs is committed to excellence in every aspect of our business. We uphold a standard of integrity bound by fairness, honesty, and personal responsibility. Our distinction is the quality of service we bring to our customers. Accurate knowledge of our trade combined with ability is what makes us true professionals. Above all, we are watchful of our customers' interests, and make their concerns the basis of our business.
Serving Chestertown, 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 Chestertown, MD and surrounding areas
Approved
Super Service Award Winner
In business since 1999
Free estimates
Warranties offered
"Mike came out promptly to inspect the roof and give us an estimate. He was very professional and answered all our questions. The crew was very hardworking and finished the job in one day despite having to hand carry all the materials up to the roof. They did a terrific job with cleanup too. Roof looks great!. I would highly recommend Complete Exteriors for anyone needing a new roof."
+10
Serving Chestertown, MD and surrounding areas
Approved
In business since 2021
Free estimates
Emergency services offered
"They were very nice and stood behind a free inspection of my roof. I would call them again if I have any future needs."
+32
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