About Chesapeake Roofing, Windows & Siding Annapolis Home Improvement Contractor

Chesapeake Roofing, Windows & Siding is a complete exterior remodeling company handling and roofing contractor siding, windows, roofing, sunrooms, doors, facia, and seamless gutters. The company is licensed, bonded and insured and a Better Business Bureau (BBB) of Greater Maryland Accredited Business.

Kurt Burkhart founded Chesapeake Roofing, Windows & Siding in 1987, after graduating from the University of Maryland. It quickly became a trusted name in the Anne Arundel county home improvement industry and local roofing contractors serving the greater Annapolis area.

Our specialty is the renovation of existing homes as opposed to new construction. This requires a great level of skill and customer service. It is a significant advantage that we offer all major exterior home improvement services, making Chesapeake Roofing, Windows & Siding a “one stop shop” for homeowners in and around Annapolis who are looking for a trusted roofing and home improvement contractor to help you meet your goals for improving home value or expanding your living space.

Chesapeake Roofing, Windows & Siding has specialized crews with more than 50 years of combined experience for each type of job. Our crews are certified as CertainTeed Master Shingle Applicators as well as Siding & Window Master Craftsmen.

Licenses & Certifications

A Trusted Name for More than 30 Years

Roofing Contractor in Annapolis MD

Finding a contractor to hire for your home improvement project is like no other purchase you’ll make. So, it’s important to go with a company that has been favorably evaluated by both customers and industry experts alike.”

– Kurt Burkhart,
Owner of Chesapeake Roofing, Windows & Siding

Satisfaction Guaranteed

Our company is dedicated to a relentless focus on customer satisfaction and to the highest standards of professionalism. When you choose Chesapeake Roofing, Windows & Siding for your home improvement project, you are guaranteed the best name products, the finest workmanship and security of knowing your job will be done right. We take great pride in our work and stand behind it 100%.

Areas We Serve

Chesapeake Roofing, Siding & Windows services central Maryland including all of Anne Arundel County, Bowie, Crofton, Severna Park, Gambrills, Odenton, Arnold, Riva, Davidsonville, Harwood, Upper Marlboro and Eastern Howard County. Contact us for a Free Estimate. Call 1-(800) 564-7230 or request an appointment online.


Chesapeake Roofing,
Windows & Siding Inc

PO Box 4524
Crofton, MD 21114
MHIC #36354