Quality. Dependability. Experience.

Chesapeake Roofing is a local Annapolis roofing and home improvement company. We serve communities in and around Anne Arundel County, MD. We are a family owned local business, and proud to be one of the area’s top trusted roofing contractors. Our customer testimonials and gallery of work is a testiment to how much pride we put in the quality of our work. Our customer service and attention to detail is unmatched.


Let our family of Anne Arundel County roofing contractors help you improve the value and comfort of your home. We provide new roof installation, replacement windows and doors, siding installation, and more. We also offer custom decks and sunrooms to expand your living space for family fun and entertaining. Our professionals are Siding & Window Master Craftsmen, and CertainTeed Master Shingle Applicators. With more than 50 years of combined experience, you can be sure that we get the job done right the first time. Receive excellent results with Chesapeake Roofing, Windows & Siding today.

Chesapeake Roofing in Annapolis MD Staff

Chesapeake Roofing has been providing quality workmanship for over 30 years to:

  • Anne Arundel County
  • Annapolis
  • Crofton
  • Bowie
  • Upper Marlboro
  • Howard County
  • Severna Park
  • & surrounding communities.
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Angie's List Best of 2020 Angie's List logo Angie's List Best of 2019 CertainTeed logo Energy Star logo Angie's List Best of 2018


Had Kurt and his crew come out and do my roof. Did a great job. No worries about leaks this winter. Thank you guys, it looks great! I will be calling back for Windows in the spring. Thanks again!!

- Audrey L.

I just wanted to write you a quick note to let you know how happy we are with our new entry door, gutters, roof, siding, and windows. Everything looks absolutely beautiful just like we envisioned it would be. We are...

- Reginald & Tayma M

I just wanted to write a short not to let you know how pleased I am with the work you did in replacing the siding for me this week. It looks great! The neighbors have even stopped by to comment....

- Noreen P.

The new roof and gutter above the front porch have been put on our home. My husband and I are very pleased by the workmanship and cleanup of your crew. It is one of the few times we have had...

- Marlene & Walter

From Our Blog

The Importance of Insulation

The cold temperatures of the winter season provide a good reminder about the importance of regulating the temperature inside your…

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New Gutters: Where to Start

Gutters catch rainwater from your roof and carry it to a designated area that will avoid damage to your home…

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Which Shingles Are Best for Harsh Winters?

Incoming winter months in Maryland can bring heavy snow, high winds, and ice. Your roof may have to endure a…

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All About Bay Windows

If your windows are drafty, ill-fitting, or outdated, you could be due to replace them. This creates an ideal opportunity…

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Chesapeake Roofing,
Windows & Siding Inc

PO Box 4524
Crofton, MD 21114
MHIC #36354