Replacement Windows in Annapolis, MD

Chesapeake Roofing, Windows & Siding, Inc. is a premier contractor in the Annapolis area for replacement windows and home remodeling services. We offer several options: Anderson Windows, Lansing Windows, and Simonton Windows. Our window installation service team will help you decide which are best for your home.

Window Replacement Annapolis, MD

Free Estimates for Replacement Windows

$100 off any vinyl replacement window job over $1,000

Five window minimum includes purchase and installation:

  • Tilts for easy cleaning
  • No Painting Windows Ever Again
  • Bow & Bay Windows Available
  • 3/4 Constant Force Balance System

Please present after the estimate given. Not valid on prior contracts. Limit 1 coupon per home.

Vinyl Replacement Windows

Wood and vinyl windows have similar performance when it comes to energy efficiency. But vinyl windows outperform when it comes to maintenance and cost. Benefits of vinyl replacement windows:

  • Affordability: Vinyl windows cost about half as much as wood windows
  • Longevity: Vinyl windows are weather, bug, and rot-resistant; they also hold up to repeated use better than wood
  • Maintenance: There’s no need to repaint or refinish vinyl windows; they’ll look as good after ten years as the day they were installed
  • Beauty: Vinyl windows are available in a range of colors, finishes and realistic-looking wood laminates

Types of Windows

  • Awning Windows: These windows have a top hinge and swing outward from the bottom. Generally, they are wider than they are tall. These windows provide excellent side ventilation.
  • Bay and Bow Windows: This style of window combines three or more windows together at an angle to allow light in and add additional space. A Bay Window consists of three windows of different sizes, while a Bow Window is three or more windows of the same size.
  • Casement Windows: Casement windows are popular in the Annapolis area. They are hinged on one side and open horizontally. These provide full ventilation for improved airflow.
  • Single-Hung & Double-Hung Windows: This is the iconic window style. Single-hung windows have a fixed top and a bottom that slides up and down. Double-hung windows are fully operable to move either section up or down. Double-hung windows also tilt, making them easy to clean.
  • Gliding or Sliding Windows: Gliding windows slide horizontally past one another. These are a great option for windows that face walkways, porches, decks or sunrooms.
  • Picture Window: Picture windows are fixed and do not open. These consist of a single piece of unobstructed glass to let in the maximum amount of natural light.
  • Specialty Windows: These windows, also called Geometric Windows, are available in a variety of shapes and sizes. Half-round windows above an entryway are a great example of a specialty window.

America’s Top Window Brands

Chesapeake Roofing, Windows & Siding, Inc. represents some of the industry’s leading brands of replacement window manufacturers. 

Wincore Windows

We offer the Wincore 5400 and 7700 series windows, which provide a variety of colors, woodgrains, glass options, grid patterns, and window styles. The 5400 series window features a contoured frame and grids, weather seals, an insulated glass unit, and a comprehensive warranty.

The 7700 series window features a beveled frame design, strong rigid units at frame corners, a U-channeled spacer system, and an insulating glass unit set ½” deep into the sash. Explore Wincore Windows at

Harvey Windows

Harvey Windows use high-performance and high-quality materials to craft their windows. Their vinyl and wood windows use a variety of styles and colors for customization.

From single and double-hung windows to windows made of custom shapes, you can find the right style of window for your house. Harvey Windows are energy efficient, offer a Clear Confidence warranty, and are made in the USA. Explore Harvey Windows at 

Anderson Windows

The name Anderson is synonymous with quality replacement windows and doors. This popular brand offers a vast selection of window styles in wood or vinyl. In 2016, Anderson Corporation was named ENERGY STAR Partner of the Year – Product Brand Owner Award by the U.S. EPA for its outstanding contribution to manufacturing energy-efficient products and consumer education. Explore Anderson Windows at

Lansing Windows

Lansing Vinyl Replacement Windows are often called the “best value in replacement windows.” We offer various options and styles to fit every need and budget. Explore Lansing Windows at

ProVia Windows

ProVia windows are designed for optimal energy efficiency and peak performance. These vinyl windows keep your home cool in the summer and warm in the winter.  ProVia Endure windows are Energy Star certified to help make your home as energy-efficient as possible. Learn more about ProVia Windows. 

Simonton Windows

Our most popular brand of replacement windows is made by Simonton, part of the trusted Ply Gem family. Simonton offers some of the best warranties in the industry. Explore Simonton Windows at

Areas We Serve

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 window installation service estimate.

Call 1-(800) 564-7230 or request an appointment online.