Chesapeake Roofing Windows & Siding

Chesapeake provides expert roofing installation and repair using premium materials like CertainTeed, GAF, and Tamko shingles. Our certified crews ensure durability, watertightness, and aesthetic appeal while extending roof lifespan. Services include steep and low-slope roofing, with solutions for leaks, missing shingles, and drainage issues.

We install vinyl, fiber cement, and composite siding from brands like James Hardie and CertainTeed. Our siding enhances energy efficiency, weather resistance, and curb appeal. Insulated options improve home insulation while requiring minimal maintenance over decades.

Chesapeake offers aluminum gutters and debris-resistant systems like Leaf Sentry and Xtreme Gutter Guard. Our installations prevent water damage, reduce maintenance, and include seamless designs for efficient drainage tailored to Maryland's climate.

We install energy-efficient vinyl windows from Andersen, Simonton, and Harvey. Features include low-maintenance frames, thermal insulation, and customizable styles like casement, double-hung, and bay windows to improve comfort and reduce energy costs.

Our door replacements include fiberglass, steel, and wood options from ProVia, Andersen, and Pella. Services cover entry doors, patio doors, and storm doors, focusing on security, energy efficiency, and aesthetic enhancement for residential properties.

Kurt founded Chesapeake Roofing in 1987, establishing a legacy of quality and trust. With decades of industry experience, he leads a team committed to excellence in every home improvement project.

We serve Anne Arundel County, Bowie, Crofton, Severna Park, and surrounding areas in central Maryland.

Yes, we provide free estimates for roofing, siding, window, and door projects with a $100 discount on qualifying jobs.

Yes, we offer financing to help homeowners manage the cost of large home improvement projects.

We stand by our work with comprehensive warranties covering materials and installation for your peace of mind.

Our crew leads have 20+ years of experience, and all team members undergo specialized training for certified installations.

We had a new front door and storm door, plus two sliders on the side and back of the house. Pricing was excellent and the work was very well done. Like everyone else, we had to wait a bit longer for the project because of supply chain issues, but they worked around that to their best by providing an alternative front door which was more expensive, but could be obtained earlier, at no additional charge. Would recommend this group any time.

Domenic came out promptly for assessments of my problem, and Victor right away figured out where the subtle leak was coming from that had eluded two handymen and one roof/gutter professional before him. Reasonable repairs were done promptly, and I just couldn't be happier to get this and some rotten door-frame wood nicely covered with aluminum. It looks great and didn't break the budget. Will definitely call this company again. thanks, Victor and Domenic!

I couldn't be happier with the service and products that I received from Chesapeake Roofing, Windows & Siding Inc. I am happy to say I have the most beautiful home on my whole block. I got a new roof, new gutters, new siding, a new surround, and a new storm door. I interviewed 5 contract companies and I am so glad I chose Chesapeake. From start to finish, everyone I communicated with provided great customer service and friendly efficient communication starting with my Sales Representative Mark Phillips, then Lisa Dodson Administrative Assistant, to Victor Uribe Site Manager, and finally Rob Burkhart Customer Service Manager.

This team represents among the highest levels of customer service I have experienced as a homeowner. Information from everyone was accurate and responses to queries were turned around very fast. The attached pictures will tell the story of how fantastic the crews did at all the work on my home. Everyone was polite, friendly, explained everything in great detail, on time, and cleaned up thoroughly. I am extremely happy with all the work and I will definitely refer to family and friends and will be using them again in the future.

Happy to leave a very positive rewiew!review! From beginning sales meeting, which was well explained by their sales rep.1 hour for accurate proposal. The job took one day for a roof consisting of 4 dormers. 12-12 pitch too. I've done roof work myself & this group of men were well insinc to maximize their labor time. Pulled off old one; installed new one in one day. Nail pick up with magnets left only 2 nails to 1 month later. Chesapeake's sign is still on my lawn because everyone that asks about our roof experience gets a big thumbs up & contact information before I let them leave!

We were initially going to go with Thompson Creek for our windows and siding needs- soooo glad I did my research! From start to finish, we had an amazing experience and ended up saving a significant amount! We had 30 windows replaced and siding redone and couldn't be happier! Without a doubt, I would recommend them to anyone looking to remodel their home! From sales, to install, to follow-up.truly outstanding! The install team were courteous and professional, and very attentive. Best customer service and love that they are family owned and operated!

We had 7 windows replaced on our home. Chesapeake Windows Roofing and Sidings performance on the project was outstanding from start to finish. We are very pleased with the quality of the product and the installation. Next up Chesapeake Windows Roofing and Siding will be replacing 4 more windows and replace the siding on our home. We highly recommend this company for your home improvement projects.

I absolutely love my new siding! Chesapeake did such an incredible job. The siding crew was friendly and efficient. Everything looks so beautiful. None of that bulky, ugly putty gobbed on where pipes and wires enter the house. It all started with a great salesman. Tony is awesome. He kept us informed and really worked with us. I changed my mind on color a couple times and he was patient and helpful.

He was not the least bit pushy or aggressive. He even went out of his way to drive by a house that I liked the color of so we could figure out the name of the color. Pacific Blue! Everyone has made comments of how nice it looks. I am so happy with their work and will use them again in the future.