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
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
"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
"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 was very responsive, the proposal very thorough, and the team completed the roof and clean up in one day. Roof looks great too!"
+10
Serving Chestertown, MD and surrounding areas
Approved
In business since 2018
Free estimates
Credit card accepted
"Very detail oriented and professional. Excellent service. Very prompt to respond and fast completion of new roof in one day. The owner of the business always answers his phone right away. I highly recommend Canales Roofing."
+12
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