Shingle Roofing Annapolis

Shingle roofing is the most popular choice for residential roofing systems. They offer the most durable and affordable choice in a wide range of styles, textures, and colors. Shingle roofs are easy to maintain and energy efficient. Chesapeake Roofing, Windows & Siding, Inc. is a leader among Annapolis roofing contractors. We provide superior workmanship, efficient installation, and a worry-free guarantee.

What Our Customers Say

I really appreciate the courteous and efficient manner in which the job was completed. My wife and I are very happy with the appearance of the new roof and skylights. I especially want to thank you for your professionalism and responsiveness to my questions. I would highly recommend your company to my friends and neighbors. – Tony C., Crofton, Maryland

Choosing the Best Shingle Roofing for Your Home

Steep Slope Roofing Annapolis, MD

Chesapeake Roofing represents some of the leading shingle roof manufacturers. We are a CertainTeed ShingleMaster™ contractor. This certification demonstrates our skill and expertise in the installation of asphalt shingle roof and enables us to offer extended warranties through CertainTeed. We also offer GAF and Tamko roofing. In offering a wide selection of shingle roof options, we can help you make the best choice for your house and budget.

Types of Roof Shingles

There are numerous options for shingle roof materials. The combination of style, texture and color is nearly limitless. The most popular types of residential roofing shingles in the Annapolis region are dimensional or architectural shingles. CertainTeed’s Landmark series: Landmark Premier, Landmark Pro, and Landmark are our best-selling shingle roof systems.

There are basically three types of shingles:

  • 3 Tab Shingles
    Timeless and economical, 3 Tab Shingles are a traditional choice for homeowners who want the combination of performance and affordability.
  • Architectural Shingles
    Also known as dimensional shingles, this option provides an added level of beauty, texture, and dimension to a replacement roof. Architectural shingles are generally thicker than 3 Tab Shingles. These are the most popular types of shingles we install.
  • Premium Shingles
    Premium, or designer shingles, are the top-of-the-line choice for homeowners. These dimensional shingles are extremely thick and crafted to match the appearance of slate, cedar, or other natural materials.
CertainTeed Landmark Shingles

Landmark is CertainTeed’s tried-and-true architectural laminate roofing shingle. Designed to replicate the appearance of cedar shake roofing, Landmark is available in an impressive array of colors that complement any trim, stucco, or siding.

  • Dual-layered construction provides extra protection from the elements
  • Ten-year StreakFighter® algae-resistance warranty
  • Priced at a fraction of the cost of traditional cedar shake

The Landmark Pro and Landmark Premier shingles are thicker and come with extended warranties.

Visit to see the full range of residential roof products.

GAF Roof Shingles

GAF is the #1 selling shingle roof brand in the United States. Like CertainTeed, they offer a range of styles, textures, and colors. Visit to see the full range of roof products.


Tamko has been producing residential roofing shingles for more than 70 years. This trusted brand offers a nearly endless combination of cut, color, and coverage to enhance the beauty of your home and provide protection you can count on. Visit to view residential shingle roof options.