Get matched with top asphalt shingle roofing repairers in Shady Side, 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!"

"I highly recommend Cox roofing to anybody who is considering having a new roof installed. They very affordable, prompt, and professional, They also communicated well from start to finish. I received before and after pictures of the project."

"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!

"Perfect. I scheduled an appointment on the Angi app, and Mike came on time. He thoroughly reviewed the damaged siding on our initial visit. The original siding around our carport had a cap over the top that fell away, and the team came up with a different way to attach the siding so that problem wouldn't happen again. The crew arrived on time on the repair day, completed the task, and reviewed it with me before leaving. They provided excellent communication and service throughout the whole process. I highly recommend them and will be calling on them again for future remodeling needs!"

"Presidential did an amazing job with our roof! They replaced all of the plywood and installed new shingles in less than a day. The new roof (and gutters!) look great. I definitely recommend this company. Plus, we plan to have them do our front door later this year. :)"

"Jimmy did a great job in pointing out old roof problems, worked out great even with delays! Roof looks really great"

"Overall the installation went well except the "bowing" in the portion of the roof over the garage. We contacted Power on several occasions, but we haven't received a proper response yet. Below is the email we sent to Power. Power did acknowledge receiving the email, but nothing has happen so far. Email: You replaced our roof April 23, 2022 – project number 35-74502. We’re pleased with the replacement except for the portion over the garage…it’s bowing. Below, is our account of the events detailing how we have tried to resolve this issue. March 26, we met with sales team, Chris Pierson and Christy. We were assured that the bowing over the garage would be addressed and corrected since we were getting a brand-new roof, down to the decking/framing. The replacement should resolve this issue unless it’s structural. Brandon, project manager came out March 30 to check the readiness of the installation; to verify the frame could support the new roof. During the appointment, he mentioned that he would be on site the day of install. The roof was replaced on April 23rd. No on-site manager ever came on site, the lead guy of the work crew was not an effective communicator. We engage beyond the one time he asked for an extension cord. I called POWER and left a message with Chris Pierson that same day after the crew left to express my dissatisfaction with the roof over the garage. POWER came out to inspect/QA the project at completion (the roof) on April 25th, I believe his name was Zach. We pointed out the concaved roof on the garage. He stated that portion may be a structural issue and Power could not address that. I asked him how much would it cost to replace it? He thought about it for a minute or so, then stated it could be replaced, but it would be “redo” and he quoted us a price of approx. $8900. He proceeded to say that he could knock it down to about $7800 if we added an additional project to replace the house trim. This is when he mentioned that they have company meetings on Tuesdays in the morning and he was sure this project would be discussed. He acknowledged that POWER’s communication could have been better (better details in the project notes). We waited few days thinking that someone from POWER would reach out and when that didn’t happen, we called Chris Pierson (the POWER sales guy) on April 28th. During this call, Chris scheduled another QA/follow up appointment for May 9th at 10:00am; he said Dylan, a service manager would come out. On May 9th no one showed up. About 10:20am, we called POWER only to find out that we did not have an appointment for that day. We were not the appointment list. We then rescheduled for 10am the next day, not even 10 minutes later POWER called back to inform us that unfortunately they were not going to be able to make it because of some staff meeting. I recall asking “is the meeting all day”. That’s when we were told that the next available date was June 16th; feeling like we had no choice we accepted the June 16th date at 6pm to allow both of us to be present for the meeting. Upset and feeling like we were about to get the runaround, we placed a call to GreenSky (financing team) to inform them of the matter since loan was activated and payments would begin soon. After sharing the situation with the GreenSky rep, she took notes, and we submitted a complaint because again we felt like we were about to get the run around. On June 12th, we had a call with the assigned GreenSky caseworker. He advised that we should continue to try and resolve the matter with POWER. On June 16th around 1:50pm, I received an apologetic call from Terry, apologizing for being late, that his prior appointment ran over, he was out in the sticks and phone reception was not all that great. I mentioned that our appointment wasn’t until 6pm as so my husband could be home. I was told that I must be mistaken because they don’t make appointments after 6pm, his latest appointment would be around 4:00pm. He said that my husband really didn’t need to present, it would be a quick look and since he was in the area. He asked for a summary of the situation; I gave him the run down. He asked if I could send him a few pictures, which I texted him a few of the garage roof. He said he got the jest of it. He apologized and asked what could they do… we said that we would be open to a knocking something off the price or repairing the area. He said let me call my office. He called us back to say that someone from senior management would be calling us to try and resolve this that evening of June 16th, but still haven’t heard from him or POWER."