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
From Left to Right: Mark Phillips (Product Specialist), Rob Burkhart (VP of Operations), Bob Burkhart (Product Procurement), Victor Uribe (Site Supervisor), Lisa Dodson (Office Manager), Domenic Cetrone (Product Specialist), Kurt Burkhart (Owner), Tony Besche (Product Specialist)

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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From Left to Right: Mark Phillips (Product Specialist), Rob Burkhart (VP of Operations), Bob Burkhart (Product Procurement), Victor Uribe (Site Supervisor), Lisa Dodson (Office Manager), Domenic Cetrone (Product Specialist), Kurt Burkhart (Owner), Tony Besche (Product Specialist)
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


Megan BrumfieldMegan Brumfield
14:20 29 Oct 22
Chesapeake did a fantastic job with our house and garage siding. The company gave us the best pricing of all other estimates we acquired. It was a great experience. I would recommend this company to anyone needing exterior services and would use them in the future for any other household needs. Do yourself a favor and give them a call.
Jon K9Jon K9
14:42 26 Oct 22
We recently had Chesapeake install all of our windows in our home. We used them as they installed the roof on our house a few years back before we owned the home. The previous owners informed us they were very please with Chesapeake. Our experience was great as well, as they were professional, efficient, and at a great price. We already have plans to use Chesapeake for future home projects!!!! Would highly recommend!!
Sandy VSandy V
11:07 19 Oct 22
CWRS replaced 2 doors in our home; entry door and storm door. The doors were not standard so had to be custom made. The process was mostly seamless and easy being emails to respond to. The doors look wonderful and work perfectly. Added bonus, I was expecting to have to repaint and clean and didn't have to do either! We have used CWRS for our windows years ago that they are still great! I would not hesitate to call CWRS for all your needs. Locally grown and owned too!
N LeeN Lee
21:30 31 Mar 22
I couldn’t be happier with the service and products that I received from Chesapeake Roofing, Windows & Siding Inc. I am happy to say I have the most beautiful home on my whole block. I got a new roof, new gutters, new siding, a new surround, and a new storm door. I interviewed 5 contract companies and I am so glad I chose Chesapeake. From start to finish, everyone I communicated with provided great customer service and friendly efficient communication starting with my Sales Representative Mark Phillips, then Lisa Dodson Administrative Assistant, to Victor Uribe Site Manager, and finally Rob Burkhart Customer Service Manager. This team represents among the highest levels of customer service I have experienced as a homeowner. Information from everyone was accurate and responses to queries were turned around very fast. The attached pictures will tell the story of how fantastic the crews did at all the work on my home. Everyone was polite, friendly, explained everything in great detail, on time, and cleaned up thoroughly. I am extremely happy with all the work and I will definitely refer to family and friends and will be using them again in the future.
Laura Burrows HavilandLaura Burrows Haviland
17:07 18 Nov 21
We had two trees fall on our house during a wind storm. Domenic with Chesapeake Roofing, Windows & Siding Inc., returned my call when no one else would! He came to the house the very next day. Kurt, Lisa, David and the entire team at Chesapeake, were professional, courteous, timely, and skilled! We are the first house in our neighborhood, and have had nothing but rave reviews from our neighbors about the improvement of the new roof, siding, and front door. I would recommend this team to anyone!

From Our Blog

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Chesapeake Roofing,
Windows & Siding Inc.

910 Soaring Eagle Court,
Davidsonville, MD 21035

PO Box 4524
Crofton, MD 21114
MHIC #36354