Quality. Dependability. Experience.

Chesapeake Roofing is a local roofing and home improvement company serving communities in and around Anne Arundel County, MD. Family owned and proud to be one of the area’s trusted roofing contractors, we take pride in the quality of our work.


Let our family of roofing contractors help you improve the value and comfort of your home with a new roof, windows or siding. We also offer custom decks and sunrooms to expand your living space for family fun and entertaining.

Chesapeake Roofing 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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Better Business Bureau Angie's List Angie's List 2018 Best of CertainTeed Energy Star


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

What To Know: The Advantages of Replacing Your Entire Roof

Depending on where you live in the DMV area, you may have experienced some bad weather such as high winds,…

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3 Benefits Of Adding A Sunroom To Your Room

Most of us call them a Sunroom, but they can also be called a Solarium, Spring Room, or even a…

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The Benefits Of James Hardie Board Siding

There are so many options when it comes to choosing which material to replace the siding on your home. Whether…

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How to Never Need to Clean Your Gutters Again

It’s spring again and that means spring cleaning! Your roof has hopefully withstood the winds of fall and the snow…

Read More


Chesapeake Roofing,
Windows & Siding Inc

PO Box 4524
Crofton, MD 21114
MHIC #36354