Get matched with top asphalt shingle roofing repairers in Arnold, MD

"I contacted Chesapeake Roofing, Windows, and Siding about installing a new roof on my townhouse. The estimate I received was actually over $1,000 LESS than what my neighbors paid last year to have their roofs replaced by another local company. I signed the contact but was contacted by my HOA board shortly thereafter who said I needed to change the type of shingle I had put in my contact as it was not the approved shingle type for our community. Chesapeake Roofing, Windows, and Siding told me it was no problem to change the shingle type and quickly drafted me up a new contact to sign. Domenic and Kurt also kept me well informed about when my new roof would be installed as the original date had to be pushed back a few days due to rain. Domenic and his crew cleaned up very well after the roof was installed - my neighbor also told me she was impressed how well they cleaned up. There was a minor issue with some gunk from the gutters that was left on my neighbors siding, however, Kurt responded immediately when I called about this and the debris was power washed clean the next day. I would definitely recommend Chesapeake, Roofing, and Siding to anyone looking to have a new roof installed based on my positive experience!"

"We hired Cox to repair/replace the both sides of the church's pitch roof at Our Lady of Hope Church in Dundalk. They took off the old roof, added plywood, new cloth and shingles. We are talking about a roof that is 1000's of square feet! The job was done within the allotted time. The clean-up was superb! The price was 17% below the closest bid price. A most excellent result from a fantastic company."

"Good price, great people. Goes the extra mile to do a quality job. Billy went to four Home Depot stores to find the exact shingle to match our church roof. Great fun working with craftsmen with old world values. Will recommend to members and friends. Albert R. Gwynnn Oak, Maryland."

"The guys were very professional and polite, they did a great job. This is the second time we have used them and we would definitely hire them again. They replaced the missing shingles, checked the entire roof, flashings, pipe sealants, and ridge vents. They sealed everything that needed touched up. They also cleaned and tightened up the gutters and downspouts. Once they were done they made sure everything was cleaned up behind them."

"Their consultant was on time and very knowledgeable. I ultimately decided to move forward with a new Roof and replacement windows. My Roof was done roughly 2 weeks later and my windows were just completed. I am very pleased and look forward to the energy savings this winter. The architectural shingles really look good and have gotten me a lot of compliments from my neighbors."

"Bought my house in 2017 and told it had a new roof. Came to find in 2025 that it had been totally botched. Shingles were coming up, there were large holes where knots in the frame had been knocked out by nails, and I had severe water damage on one of my trusses. Roof Pups came out, assessed the damage, worked with me on the price, and in less than a week I had a crew on site that fixed everything in a single day. They were here for over 12 hours making sure the job got done and they did a great job. I couldn't be happier with my experience."

We specialize in roofing and siding inspection, repair and replacement as well as gutter repair and replacement. We have the experience and dedication to bring your dreams to reality! We pride ourselves on the quality work we provide, while delivering great customer service. Call or click to schedule a free inspection and estimate today!

"The roofing crew was phenomenal. They did something I have never seen before—they put tarps on all the bushes around the house. In addition to the shingles, they also had to replace all the wood under it. They did beautiful work! They treated our property with the care they would have used on their own homes."

Here at HomeMatters, LLC, we believe in the people we work with and work for. We measure our own teams with not only the pride they take in their work and results, but the measure of respect and integrity they have for each other, our clients, and the project at hand. All of our technicians are certified master installers with over 30 years of experience, working hard to make a change to the reputation of the business we're in. We aim towards educating our customers and lending as much advice as we can towards any remodeling project, whether it is a repair or an installation. Allow us to listen to your needs, and to share the vision you have for your home.

"Very pleased with the entire roof install project. I would recommend them to anyone looking for roofing repairs. Dylan and Allan's crew handled everything seamlessly from start to finish."