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
"Great. They were able to do the same week we called. Looks very nice and matches roof on home"
+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
Super Service Award Winner
In business since 2004
Free estimates
Emergency services offered
"The staff at Home Genius were very knowledgeable and friendly. Our roof was installed sooner than expected and looks amazing. Best looking roof on our street! Definitely recommend Home Genius if you’re in need of a new roof."
+73
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
"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 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
"THE ROOF WAS REPLACED QUICKLY AND EFFICIENTLY WITH NO WASTE OF MATERIAL OR TIME. THE CLEAN-UP WAS TOTAL AND THEY LEFT ME NOTHING TO DO BUT ENJOY MY HARBOR BLUE ROOF. I HAVE RECEIVED MANY COMPLIMENTS. ONE SUGGESTION IS: SIGNAGE FOR AML WAS NOT PUT ON THE LAWN. THANK YOU CASEY AND YOUR PLEASANT WORKMEN."
Serving Chestertown, MD and surrounding areas
Approved
Super Service Award Winner
In business since 1999
Free estimates
Warranties offered
"Excellent customer service for a first time person having a roof done. If I ever do it again I would still choose complete exterior. Excellent job based on the opinion of someone who knows roofing i love it! Job started and completed on time just like they said it would be. Very good job of cleaning up and putting things back as they were. I would truly recommend them to a friend."
+10
Serving Chestertown, 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
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