Chesapeake Roofing, Windows & Siding Inc. is a premier contractor in the Annapolis area for window replacement and home remodeling services. We install multiple product lines, including Andersen window options and Simonton window styles, and our team will help you choose the best fit for your home.
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(800) 564-7230Window Replacements in Annapolis, MD
$100 OFF
Any Vinyl Replacement Window Job Over $1000
Free Estimates for Window Replacement
$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.
What affects window replacement cost? Pricing typically depends on how many windows you’re replacing, window size and style, frame material, glass package, and the amount of trim work needed for a clean, sealed finish. If you’re planning a larger project, ask about window financing options so you can choose the right timeline without compromising on quality.
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 We Can Install
Window replacement is not one size fits all, because each room needs the right balance of ventilation, sightlines, and easy cleaning. If you want to see real finished projects, browse our window gallery photos.
- 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 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.
When to Schedule Window Replacement
Most homeowners start thinking about window replacement when comfort drops, drafts show up, or condensation appears between panes. If you are seeing fogging, sticking sashes, visible frame wear, or rising energy bills, replacing older windows is often more cost-effective than repeatedly repairing one problem at a time.
- Drafts you can feel near frames
- Condensation or fogging between panes
- Windows that stick or will not lock
- Noticeable outside noise indoors
- Water staining around trim
If you are looking for quick ways to improve comfort while you plan next steps, use these window efficiency improvement tips to identify common sources of heat loss.
What to Expect During Window Replacement
A window replacement project typically starts with measurements and product selection based on performance, maintenance needs, and style. On installation day, the team protects the work area, removes the old unit, verifies the opening, and installs the new window so it is level, sealed, and properly trimmed. A final walkthrough confirms smooth operation, tight locks, and clean interior and exterior finishes.
To make the appointment efficient, review these contractor consultation tips before your estimate.
Top Brands for Window Replacement
Chesapeake Roofing, Windows & Siding Inc. represents some of the industry’s leading brands of replacement window manufacturers.
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. Learn more about Wincore window options.
Harvey Windows uses high-performance and high-quality materials to craft its 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. Review Harvey window options.
The name Andersen is synonymous with quality replacement windows and doors. This popular brand offers a vast selection of window styles in wood or vinyl. Andersen Corporation has been recognized for its contribution to energy-efficient products and consumer education. Explore Andersen window options.
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, and many options are Energy Star certified to support efficiency goals. See ProVia window options.
Our most popular brand of replacement windows is made by Simonton, part of the trusted Ply Gem family. Simonton offers strong warranty coverage and a wide range of styles. Compare Simonton window styles.
Areas We Serve in The DMV
Chesapeake Roofing, Windows & Siding Inc. 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 (800) 564-7230 or request an appointment online.
Window Replacement FAQs
If you are seeing drafts, sticking sashes, fogging between panes, or rising energy bills, the signs in this replace windows this fall guide can help you decide whether replacement makes more sense than repairs. The best timing is usually before temperatures swing again, so you can lock in comfort and avoid preventable damage.
Yes, especially when your current windows leak air or have failing seals, and these boost window efficiency tips explain the upgrades that typically make the biggest difference. Savings vary by home, but most homeowners notice more consistent indoor temperatures right away.
The best fit depends on ventilation, cleaning needs, and how the room is used, and this right windows for home overview breaks down common options in a practical way. If you want a faster decision, start with the rooms where you feel drafts most often.
Before the visit, use these prepare for consultation steps to gather questions, identify problem rooms, and clarify your priorities for style, maintenance, and efficiency. That prep helps the appointment stay focused and makes recommendations easier to compare.
Start by using the request a free estimate form so we can review your goals and confirm the next steps for measurements and options. After that, our team will follow up to schedule a time and answer any questions you have.
See What Our Customers Are Saying About Us!
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"I was very impressed with the entire process. The crew was professional and did an excellent job installing my roof and gutters. They cleaned up thoroughly and left the place even better than they found it. I highly recommend Chesapeake Roofing!"
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