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Chesapeake Roofing Windows & Siding Chesapeake Roofing is a local Annapolis roofing and home improvement company. We serve communities in and around Anne Arundel County, MD. We are a family owned local business, and proud to be one of the area's top trusted roofing contractors. Our customer testimonials and gallery of work is a testiment to how much pride we put in the quality of our work. Our customer service and attention to detail is unmatched. Let our family of Anne Arundel County roofing contractors help you improve the value and comfort of your home.
Services
Chesapeake Roofing, Windows & Siding is a complete exterior remodeling company handling and roofing contractor siding, windows, roofing, sunrooms, doors, facia, and seamless gutters. The company is licensed, bonded and insured and a Better Business Bureau (BBB) of Greater Maryland Accredited Business.
For more than 30 years, Chesapeake Roofing, Windows & Siding has been a trusted name in Anne Arundel County, Maryland for exterior home remodeling. Our specialty is the renovation of existing homes as opposed to new construction. As an experienced Maryland based roofing contractor and home improvement specialist, we handle all aspects of exterior home improvements including roofing, siding, widows and doors, porches, sunrooms, decks, seamless gutters and facia.What sets us apart from other home improvement contractors in Maryland is our relentless focus on customer satisfaction.
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Thank you (and your crew) for the time and attention to all the details on the house. The house looks great, and I'm looking forward to the first winter with decent windows and some extra house insulation under the siding. I would recommend your company without hesitation. I want to thank you for the excellent job your crew did with the installation of my kitchen windows.
Reviews (10)
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Joe Biddle
Jun 02, 2022
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.
Wendy Banks
Apr 24, 2022
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!
N. Lee
Apr 18, 2022
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.
Tom Schaeffer
Apr 16, 2022
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!
Faith Ihnat
Mar 16, 2022
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!
Jerry Rowe
Dec 13, 2021
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.
Jeannine Wendland
Dec 06, 2021
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.
Laura Burrows Haviland
Nov 27, 2021
We had two trees fall on our house during a wind storm. Domenic with Chesapeake Roofing, Windows & Siding Inc., returned my call when no one else would! He came to the house the very next day. Kurt, Lisa, David and the entire team at Chesapeake, were professional, courteous, timely, and skilled! We are the first house in our neighborhood, and have had nothing but rave reviews from our neighbors about the improvement of the new roof, siding, and front door. I would recommend this team to anyone!
David Manion
Nov 18, 2021
We chose Chesapeake Roofing, Windows & Siding Inc. when it was time to replace our roof. They were recommended by a friend in the construction business. Chesapeake Roofing, Windows & Siding did an excellent job installing the roof and in cleaning up the debris from the removal and installation. They even replaced several weak plywood panels in the process, bringing our roof back to like-new. I highly recommend them.
Lauren Bacco
Nov 15, 2021
Tony came out and provided us an estimate for replacing 2 skylight windows. He was on time, professional and friendly. After comparing a few quotes I reached back out to Tony and I told him we wanted to move forward with the project. He sent the contract over the same day for us to sign. Once the office received our deposit they called to schedule the work.

Very smooth process. Work was finished in less than 1 day and hardly any mess was made on the inside of the house. We are extremely satisfied with the work Chesapeake Roofing did and would highly recommend them.