Annapolis Roofing Company

It’s important to have a good roof over your head. A lot depends on it, including the value of your home. Chesapeake Roofing has been in business for over 30 years. We are high-quality roofing contractors and provide home improvement services throughout Annapolis and central Maryland.

Our specialty is renovating existing homes. A roof replacement is something most homeowners will have to do at some point to maintain the integrity of their structure and the value of the home. We make the process as easy and efficient as possible. The most important things when choosing a new roof are durability, water tightness and aesthetics. Let the experts at Chesapeake Roofing, Windows & Siding, Inc. help you make the best selection for your home.

What Kind of Roof Are You Looking For?


Shingle Roof Annapolis Low Slope Roof Annapolis Roof Repair Annapolis


Free Replacement Roof Estimate

Chesapeake Roofing Offers Free Estimates + $100 off Your Project*
Call 1-800-564-7230 or request an appointment online.
*$100 off any complete roofing job over $1000. Not valid on prior contracts. Limit one discount per home.

Choosing an Annapolis, MD Roofing Company

When you choose Maryland-based Chesapeake Roofing Company, you are guaranteed the best name products, the finest workmanship and the security of knowing your job will be done right. We take pride in our work and stand behind it 100%. We focus primarily on shingle roofs but also offer low-slope roof options. There are various types of shingle roofing available and we will help you choose one that’s right for your home and budget.

We Offer the Best Shingle Roof Options

Annapolis Roofing Project

Chesapeake Roofing, Windows & Siding, Inc. is a CertainTeed ShingleMaster™, which certifies that we are able to master the complex requirements of installation for CertainTeed products. It also enables us to provide warranty extensions. In addition to CertainTeed, Chesapeake Roofing also offers GAF and Tamko shingle roof systems. We will help you choose the best shingle roof system for your house and budget.

Our Service Areas

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.