Redding, CT Roof Replacement with New Skylights and Custom Copper Chimney Flashing
Not every roofing project is just about replacing shingles.
This recent project in Redding, Connecticut involved a complete roofing system upgrade, including a new GAF roofing system, new skylights, siding repairs, and custom copper chimney flashing with a newly built roof cricket designed to improve drainage and protect the home from water intrusion.
The result is a roof that not only looks better, but performs better in Connecticut’s challenging weather conditions.
The centerpiece of this project was the installation of a new GAF asphalt shingle roof.
A quality roofing system is about more than shingles alone. Proper underlayment, ventilation, flashing, and installation techniques all work together to protect the home from wind, rain, snow, and ice. By replacing the aging roof with a modern GAF system, this homeowner gained both improved curb appeal and long-term protection.
As part of the project, we removed the existing skylights and installed new units.
Skylights are often one of the first areas where roofing problems develop. Aging seals, deteriorated flashing, and improper installation can all lead to leaks over time. Replacing the skylights during a roof replacement allows the entire system to work together and helps ensure a watertight installation.
The new skylights provide natural light while improving the overall performance of the roof.
During the course of the project, damaged and deteriorated siding sections were repaired as needed.
Addressing these issues during construction helps protect the building envelope and ensures the finished project looks cohesive from every angle.
Custom Copper Chimney Flashing
One of the standout features of this project was the custom copper flashing installed around the chimney.
Flashing is one of the most important waterproofing components on any roof. It creates the transition between roofing materials and vertical surfaces, helping prevent water from finding its way into the home.
Copper flashing is widely considered the premium choice because of its durability, longevity, and appearance. Unlike many other materials, copper can last for decades while developing a beautiful natural patina over time.
For homeowners interested in learning more about chimney flashing, see our guide to chimney flashing repair and replacement.
The chimney on this home also received a newly constructed roof cricket.
A roof cricket, sometimes called a roof saddle, is a small peaked structure built on the uphill side of a chimney. Its purpose is simple: redirect water and melting snow around the chimney instead of allowing it to collect behind it.
Without a cricket, water, leaves, debris, and snow can become trapped at the back of the chimney. Over time, this increases the risk of leaks, ice buildup, and premature roof deterioration.
By splitting the flow of water and directing it around the chimney, the cricket helps protect one of the most vulnerable areas of the roof system.
In New England, where snow and ice are a fact of life, properly constructed chimney crickets can play a significant role in preventing future roofing problems.
Between the new GAF roofing system, updated skylights, siding repairs, custom copper flashing, and newly constructed cricket, this Redding home received a complete upgrade designed to perform for years to come.
Projects like this highlight an important reality of roofing: the details matter. Proper flashing, drainage, and waterproofing are often what separates a roof that lasts decades from one that develops problems long before it should.
If you’re considering a roof replacement in Redding, Ridgefield, Newtown, Danbury, or elsewhere in Fairfield County, George’s Seamless Gutters and The Roofing Pros of Westchester can help you evaluate your roof and identify opportunities to improve both performance and appearance.










