Roofing, Siding & Windows Contractor in Pasadena, MD

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If you have drafty windows, damaged siding, or a leaky roof, it may be time for a replacement. Without repair or replacement, these problems can cost more to fix over time. Chesapeake Roofing, Windows & Siding Inc. is your trusted roofing contractor in Pasadena, MD. Whether you need new roofing, windows, doors, or siding for your home or business, we’re here to help. We’ll work with you to renovate your home with beautiful and top-quality materials.

Why Choose Chesapeake Roofing, Windows & Siding Inc.?

At Chesapeake Roofing, Windows & Siding Inc., we have over 50 years of combined experience in roofing, windows, doors, and siding. Our crews have all the necessary licenses and warranties to ensure high-quality, expert work. We’re a Better Business Bureau (BBB) of Greater Maryland Accredited Business.

Since the 1980s, Chesapeake Roofing, Windows & Siding Inc. has served Maryland clients with hard work at fair prices. We continue to serve the Pasadena area and all of Maryland.

Roofing, Siding & Windows Contractor in Pasadena, MD

Roofing Company in Pasadena, MD

Proper roofing can increase your home’s energy efficiency and reduce the risk of leaks and damage. Chesapeake Roofing, Windows & Siding Inc. provides residential and commercial roofing services in Pasadena, MD.

We can replace your home’s fascia, gutters, and roof if you need a new roof.
Our crew can provide roof maintenance once a year.
We can apply coatings to protect and waterproof your roof.

At Chesapeake Roofing, Windows & Siding Inc., we offer top-brand shingles:

CertainTeed Landmark Shingles: These premium shingles combine strength with beautiful designs. They’re built to last and come in a variety of colors to enhance your home’s curb appeal.
GAF Shingles: As America’s top roofing brand, GAF shingles provide excellent protection against wind, rain, and extreme weather. They’re designed to keep your home safe for decades.
TAMKO Shingles: These shingles provide great quality at an affordable price. TAMKO shingles deliver great performance without breaking the bank.

We can work on steep-sloped and low-sloped roofs and provide emergency roof repair if needed. As part of our specials, we offer $100 off any complete roofing job over $1000.

Siding Contractors in Pasadena, MD

Your home’s siding can protect you from the elements, but rodents and bugs can also enter through it. Cracks in the siding can let the outside into your home. Siding not only protects your home from damage but can also increase the home’s curb appeal. Solid and clean siding will create a seamless and modern look.

Chesapeake Roofing, Windows & Siding Inc. can replace or repair your siding with energy-efficient options. In addition to vinyl siding, we offer fiber cement as an alternative to wood or cedar siding. It mimics the look of wood but does not require as much maintenance.

We provide siding replacement and repair with these siding brands:

Our professional siding contractors are skilled in installing a variety of siding styles to fit your home’s look and needs. We offer vertical vinyl siding, horizontal vinyl siding, and shingle-style siding. Each option comes in different colors and designs, so you can choose what works best for your home’s style and personality.

Professional Siding Replacement

Before we begin any siding repair or replacement, we carefully inspect your home’s exterior to see what needs to be done. If there are damaged areas, we remove the old or broken siding first. Then, we check the layer underneath the siding for any issues. If we find any holes, cracks, or rot in the under-layer, we fix those areas to make sure your home is properly protected.

Once the surface is clean and solid, we prepare it for your new siding. This step helps make sure your new siding will last a long time and stay firmly in place. We always install siding from the bottom up, which is the best method to keep water out and ensure a secure, even finish. Our goal is to give your home strong, long-lasting protection—and a fresh, updated look.

You should get high-quality siding within your budget. We offer siding specials, including $100 off complete siding jobs over $1000.

Roofing, Siding & Windows Contractor in Pasadena, MD

Pasadena Window Contractors

A drafty or leaking window can let bugs, moisture, and wind into your house. Whether you have a damaged window or want to let more light into your home, we can help.

Types of replacement windows we provide in Pasadena, MD, can include:

Bay windows
Bow windows
Single-hung windows

Double-hung windows
Sliding windows
Awning windows

We can also create specialty windows with geometric shapes to fit your home’s style. When you choose us for window installation, we provide windows that are energy efficient, safe, and installed correctly the first time.

We use ENERGY STAR®-certified windows, which means they meet high standards for energy savings. These windows are specially designed to keep your home cooler in the summer and warmer in the winter, so you don’t have to rely as much on your air conditioner or heater. This helps you save money on your energy bills every month. They also reduce drafts and help maintain a steady, comfortable temperature inside your home.

We know your time is important, which is why our team works hard to provide fast but careful installation. We make sure every window is sealed tightly and installed correctly to prevent leaks and keep out water, wind, and pests. A proper installation also helps maintain your home’s temperature, so your heating and cooling systems don’t have to work as hard.

Keeping your home and family safe is important to us. That’s why we offer windows with extra safety features, like laminated or reinforced glass. These options make it harder for someone to break the glass, helping protect against break-ins and accidents. We also offer secure latches and locking systems to keep each part of the window safely closed. Window restrictors are a great choice if you want to let in fresh air without opening the window all the way.

You can also get $100 off any vinyl replacement window job over $1,000 as part of our specials. This special is best for five windows minimum.

Get New Roofing, Siding, or Windows in Pasadena, MD

Our experienced contractors will work with you to create your new and improved home. Get a free estimate from Chesapeake Roofing, Windows & Siding Inc. on our website.

You can also call (800) 564-7230 with questions throughout your home project. We will be glad to help.

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!"

- Ronald M.

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©2025 Chesapeake Roofing, Windows & Siding Inc.

All Rights Reserved

Privacy Policy

License: #126792

©2025 Chesapeake Roofing, Windows & Siding Inc.

License: #126792

All Rights Reserved

Privacy Policy

©2025 Chesapeake Roofing, Windows & Siding Inc.

License: #126792

All Rights Reserved

Privacy Policy