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    Chesapeake Roofing, Windows & Siding

    4.5 (54 reviews)
    Open • Open 24 hours

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    Imagine look after I finish Painting storm door black and wrapping columns in white.

    My home is 43 year old and was looking worn out. The thought of a whole house siding job was overwhelming to me and I was having difficulty finding the right contractor for the job. Luckily I called Chesapeake Roofing, windows and siding and ended up working with Mark Phillips, who took the time to meet with me on numerous occasions and talk me through the materials, the process and the design elements. He took the time to create a computer model and mocked up every color/style combination I was considering and gave me honest feedback. Mark made this whole process way less stressful for me, which is something I truly appreciated. Once I made my choices on materials it was a quick turnaround to the work starting. Dring the construction they found some water damaged wood near my chimney. They stopped the work. Robbie, the owner of the company, notified me and met with a carpenter to assess the situation. He then waited till I got home from work to explain and show me the rot in the framing wall and what needed to be done to repair. Next morning a repair crew fixed the water damage and the same day Mr Kim and his siding crew followed to finish the siding job. That kind of attention to detail and attention to customers is what makes a company stand out from the others and made this such a positive experience. The house looks amazing! The work and materials are top notch! And I got to support a Locally owned business.

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    30 days ago

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    10 months ago

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    2 years ago

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    Robert B.

    Thanks for the kind words. It was a pleasure doing business with you.

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    7 years ago

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    2 years ago

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    3 years ago

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    7 years ago

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    8 years ago

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    6 years ago

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    9 years ago

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    4 years ago

    They never followed through on setting up an estimate. We spoke once and then they disappeared.

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    4 years ago

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    7 years ago

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    6 years ago

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    8 years ago

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    Robert B.

    Thank you for your business and kind words.

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    8 years ago

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    13 years ago

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    Page 1 of 2

    Ask the Community - Chesapeake Roofing, Windows & Siding

    Review Highlights - Chesapeake Roofing, Windows & Siding

    “Victor, of Chesapeake, did a great job as estimator, and told us how their company would bring an outdated item up to current standards.”

    Mentioned in 3 reviews

    Read more highlights

    Winfield Builders

    Winfield Builders

    (43 reviews)

    I hired Winfield Builders to replace two old skylights in my Rockville home, and Zach and his team…read morewent above and beyond. My project was complicated because my 1980s drywall shafts were the wrong size for modern solar blinds. Instead of just "making it work" or creating a huge mess with drywall dust, Zach proposed a brilliant custom solution: building a clean birch veneer box with custom trim. It looks stunning and kept my house completely dust-free. What impressed me most was Zach's integrity. During the install, a small piece of my old plastic molding snapped. Instead of ignoring it, Zach took full ownership and replaced the trim on both skylights with upgraded foam-backed wood molding at his own expense to ensure everything was airtight and uniform. It is not a simple fix but an upgrade, for free. See the attached before/after pictures and the broken plastic. Like most customers, I contacted a few contractors before selecting Winfield Builders. Their price is VERY reasonable, and the communication through Yelp was professional and transparent. It is rare to find a contractor who cares this much about the details. If you want a crew that is honest, skilled, and delivers a beautiful finish, call Zach. 1000% recommendation!

    I've hired Winfield Builders twice, once to replace my roof in summer 2021 and again in summer 2022…read moreto replace my gutters. Zach made a strong impression from the start--when he came out to inspect my roof and I told him of a problem area, he went up on the roof to look at it! Replacing the roof took only one day, the crew arrived early and worked very hard. I also had the gutters replaced, opting for 6" gutters. The larger size has made a huge difference, as they're less likely to get clogged. My home is in good shape thanks to Winfield Builders!

    American Windows & Siding of Virginia

    American Windows & Siding of Virginia

    (83 reviews)

    Yep, another five star review for American Windows…read more We received three estimates for replacing three windows, a French door and a picture window. American Window undercut the estimates of the other two vendors by a substantial margin. We also really liked they only asked for a modest down payment. Jay was our sales contact at American Windows and he was absolutely great. He has an engaging personality, and kept all his commitments to us. We appreciated that when installation day came, he swung by to ensure all was going well. Oh, how did the installation go? It was fantastic. Not only did the windows and door come earlier than promised, the American Windows crew came on time and worked quickly and professionally. We were amazed that the whole job only took 4 1/2 hours to complete. The windows and door materials are high quality and we are very satisfied with the results.

    After a frustrating, high-pressure sales pitch from another company, we turned to Reddit and saw…read moreincredible reviews for American Windows and Siding. We decided to drive an hour out to their showroom without calling first. Even though they weren't open yet and are by-appointment-only, Phil greeted us without hesitation.It turned out they couldn't take on our small window sill repair since they didn't install the original window, but Phil helped us anyway! He gave us repair ideas, explained potential causes, pointed us toward the right tools, and gave us contacts who could help. To top it off, his cuddly dog Wilson kept us company, and Phil even recommended a local spot for lunch since he knew we had a long drive. We are completely speechless at his kindness and support, despite not even being paying customers. Based on this first impression, we would work with Phil any day. The world needs more people like him!

    New Dominion Exteriors - New Certainteed integrity roof system

    New Dominion Exteriors

    (29 reviews)

    As a first time homeowner it is so important to feel comfortable and confident in the contractors…read morethat work on your home. I got several quotes from other gutter replacement groups in the area, and when I first met Charlie I instantly knew he is who I wanted to hire to replace our very cool (but old and failing) front gutter. He was always prompt, got us on the books quickly, explained everything throughly, his crew (AND him) were at my house 30 mins early for the job, and everyone was very respectful and cleaned up after the job was completed. Charlie even helped me better understand my home beyond the gutters (and gutter guards). On top of all of that, the quote was just slightly higher than the cheapest quote I got--absolutely worth it. Definitely recommend!

    We needed a single decorative window shutter replaced, and most companies either wouldn't take on…read moresuch a small job or required a high minimum cost. This company was the only one willing to waive their minimum to help us out and I'm so glad we found them! They were incredibly patient throughout the process, helping us locate the exact replacement and making sure the color perfectly matched the existing shutters. They even went the extra mile by replacing the neighboring shutter as well, just in case there was any fade difference between new and old. A special shoutout to Charlie, who helped us and also did the work -- he was amazing! Extremely communicative, kind, and respectful. He kept us informed every step of the way and truly cared about getting everything perfect. This may have been a small project, but they treated it with first-class service. If you're looking for a siding or exterior company that values its customers and does quality work, look no further.

    Chesapeake Roofing, Windows & Siding - roofing - Updated September 2026

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