CHESAPEAKE ROOFING WINDOWS & SIDING logoApproved Pro
Approved Pro

CHESAPEAKE ROOFING WINDOWS & SIDING

Roofing, Siding Service, Window Service,

About us

Looking for top-notch roofing, windows, and siding services in Maryland? Look no further than CHESAPEAKE ROOFING WINDOWS & SIDING. With our MHIC LICENSE #126792, we deliver exceptional craftsmanship and customer satisfaction. Contact us today for all your home improvement needs!

Business highlights

Se habla espanol
Family owned & operated
LGBTQ+ Friendly
38 years of experience

Services we offer

ROOFING, WINDOWS, DOORS, VINYL SIDING, HARDIE SIDING, GUTTERS, AND GUTTER GUARDS.

Amenities

Eco Friendly Accreditations

Yes

Free Estimates

Yes

Warranties

Yes

Senior Discount

2%

Accepted Payment Methods

  • Financing Available
  • Check
  • CreditCard
Reviews
4.997 Reviews
Number of StarsImage of DistributionNumber of Ratings
5
98%
4
0%
3
0%
2
0%
1
2%

Filter reviews by service

Showing 1-25 of 97 reviews
Nancy M.
Apr 2023
5.0
Window Service
Yes, I recommend this pro
$26,000
David and his window installation team are incredibly hard working and professional. They have a strong commitment to excellence and work diligently to ensure everything is done well. David answers questions and explains options thoroughly. We would definitely do business with Chesapeake Roofing in the future based on our experience.

Barbara D.
Mar 2023
5.0
General Remodeling
Yes, I recommend this pro
Excellent service from initial communication as to my needs; performing the work needed; completing the service in a timely manner and reasonable fee for time and labor. This is my second experience with Chesapeake Roofing, the first also an excellent service provided and now my go to for future needs.

SHEILA M.
Feb 2023
5.0
Roofing
Yes, I recommend this pro
$2,400
They were professional, responsive and identified the specific repair needed to address the problem. They were timely and proactive. Other companies tried to "upsell" a total roof replacement, and that was not Chesapeake's approach. I appreciate the care Chesapeake took to figure out the source of our leak and come up with an effective solution that did not blow our budget. Will definitely contact them again in the future.
Response from CHESAPEAKE ROOFING WINDOWS & SIDING
"Thank you for your business and kind words."

N Q.
Jul 2022
5.0
Window Service, Framing Service
Yes, I recommend this pro
I am extremely satisfied with the product and services. The installation was efficient and properly done. I have used this company before for roofing and trust their work.

Albert S.
Jul 2022
5.0
Roofing, Door Service + 1 more
Yes, I recommend this pro
$14,000
They went above and beyond! For the roof, There more work than anticipated due to a second set of shingles underneath the top layer. The roofers started at 7:30 AM and did not finish until 9 PM. And they cleaned up absolutely BEAUTIFUL. The next morning I was shocked at how wonderful they did. Plus the workers were respectful and worked non-stop.

Sharon A.
Jun 2022
5.0
Roofing, Window Service + 1 more
Yes, I recommend this pro
All jobs (roofing, windows and shutters) were performed in a timely manner; staff is knowledgeable and responsive to requests for info. On-site staff arrive on time, prepared to work and completed all jobs quickly. Would highly recommend Chesapeake Roofing, Windows and Siding. We plan to use them in the near future for additional window replacements.

Kyle V.
Dec 2021
5.0
Gutter Repair and Replacement, Door Service
Yes, I recommend this pro
Great! Helped us with the selection and then when some of the items came in damaged they made sure it was taken care of. In the end, we are super happy with the door and the workmanship. They came recommended and I can second that. They also did some needed gutter work as an add on - glad we used them. We will use them again when we have a need.

Donna M.
Sep 2021
5.0
Roofing, Framing Service
Yes, I recommend this pro
$1,760
Great. They were able to do the same week we called. Looks very nice and matches roof on home

William S.
Feb 2021
1.0
Roofing
$15,000
The owner, Kurt Burkhart, proved himself to be non-trustworthy, unprofessional and unreliable. I signed a contract for roof replacement (in large part because he is a neighbor) with the stipulation the work was to be done when the Governor lifted the Emergency Declaration. In exchange for my 1/3 down (~$5,000) he said he would absorb all subsequent price increases. This week he decided to walk away from the contract because he didn't like the terms anymore. I got my downstroke back but really? GUESS WHAT HIS WARRANTY IS WORTH? Good riddance to bad rubbish. Use at your own peril.
Response from CHESAPEAKE ROOFING WINDOWS & SIDING
"Thank you Angies' List for the chance to respond to this review. Regarding this matter, the customer signed the contract over 8 months ago in June of 2020. He wanted to wait before starting because he was concerned about the Corona virus. We told him that we could postpone the work but were unaware that he wanted to wait until the Governor lifted the Emergency Declaration. That was never put in the contract, and I would never agree to that because we had no idea when it would be lifted. I had given the customer a discount on his contract because he was a neighbor, and we had done a number of his neighbors' roofs who were very satisfied with the work we did. I called the customer earlier this week and explained to him that I have been in business for more than 35 years and have always treated my customers very fairly. In the last 8 months, I had 3 price increases from my manufacturers and was expecting another couple of price increases in the next 3 months of 2021. I informed him that Chesapeake could install his roof with no up-charge, but if he wanted to continue to put off the install date that he would need to pay for any future price increases. He declined. Therefore, I told him I would provide him a full refund that day, and void the contract, which he accepted. We have completed between 5-10 roof jobs per week for the last 8 months with no issues, as I explained to the homeowner. I also explained that we wouldn't need to enter his house and that he wouldn't be in contact with any of the crew. I have done my utmost to oblige this customer, to no avail. Thank you for reading my response."

Sandra F.
Jan 2021
5.0
Roofing, Framing Service
Yes, I recommend this pro
Went great. They were out quickly to look at the issue and within a few days the repair was made. First, they came out and put up protective covering until the repair could be made.

Margaret S.
Nov 2020
5.0
Window Service, Door Service
Yes, I recommend this pro
$5,000
The job exceeded our expectations. Installers arrived on time. Installation was extremely well done with minimal impact on our activities. Work area, both inside and outside, was cleaned. There were no signs of work being done. Sales process went smoothly. Good explanation of product and procedures for installation. Of all the work we have had done on our house, this one went the smoothest - no collateral damage! We will be using them again, shortly, for additional windows.

Connor T.
Nov 2020
5.0
Roofing
Yes, I recommend this pro
$4,500
Chesapeake Roofing provided an all-around great service. They were pretty quick to get back to me when I inquired about an estimate and they were quick to set up a date to come out and give me a quote. Their pricing was about on par with other quotes I had received and they were able to set up a date for the replacement a week after I received the estimate. The day of the job, they were out there early and were done just after noon. They did a fairly decent job cleaning up, although they did miss a couple of nails and shingles. This was my first experience having a roof replaced and I'm very satisfied with the work that Chesapeake Roofing did.

Cindy G.
Oct 2020
5.0
Siding Service, Door Service + 1 more
Yes, I recommend this pro
$17,000
Absolutely top quality from start to finish. I can’t say enough about Domenic and the crew. No sales pressures and went above and beyond every step from start to finish. Their crew is absolutely high quality and made sure everything was done right down to details that I hadn’t even thought of. This company makes sure things are perfect. I was so impressed I asked them for additional projects and will absolutely call them when it’s time for roofing. Do not hesitate on giving them a call, you won’t be disappointed and this is coming from a very detailed customer. I wish all service oriented companies were like them.

Anne P.
Oct 2020
5.0
Siding Service, Gutter Repair and Replacement
Yes, I recommend this pro
$43,000
Chesapeake Roofing was a pleasure to work with from beginning to end. Every member of the team is knowledgable, professional and polite. The estimate for the service was accurate and very reasonable compared to other companies. I would highly recommend them to others and would not hesitate to use them again in the future. The owner Kurt Burkhart is visible and involved in the project. A great company and a great service!

Ashley M.
Oct 2020
5.0
Roofing, Siding Service + 3 more
Yes, I recommend this pro
$50,000
Amazing -- The team on site was very professional, and staff were very responsive via email and phone which was critical as we were out of state during this project. There were bumps as any remodel will have - but this team was patient and responsive in correcting issues and attained beautiful results. We would recommend this team to anyone looking for siding, roofing, windows in the Crofton area.

Rosie G.
Sep 2020
5.0
Siding Service, Gutter Repair and Replacement + 1 more
Yes, I recommend this pro
They were so nice, punctual, and professional. We got 4 estimates and dealt with several companies, not only were they reasonably priced we went with them because of the way they treated us. They went beyond explaining in detail what they were doing. They gentlemen that preformed the work were very kind, clean and professional. They cleaned up so well. We are beyond happy with their work.

Marie R.
Jul 2020
5.0
Roofing
Yes, I recommend this pro
$6,000
I was very happy with the roof replacement that Chesapeake Roofing recently did on my home in Heritage Harbour in Annapolis. The salesman/estimator was quick and thorough, and always gave fast responses to my questions. The installers did a great job, carefully tarping the flower beds and deck to protect them and making a thorough sweep for nails and debris when they were finished. I couldn't be happier with the end result, and won't hesitate to recommend Chesapeake Roofing to my friends and neighbors.

ELIZABETH E.
Jul 2020
5.0
Roofing, Gutter Repair and Replacement
Yes, I recommend this pro
Chesapeake Roofing was excellent. Their price estimate was the best of five, and there were no extra charges upon completion. They were responsive, prompt and courteous. Our roof was replaced skilfully and all debris was removed cleanly. I would highly recommend Chesapeake Roofing to anyone...they're the BEST!!

B S.
Jul 2020
5.0
Roofing, Door Service
Yes, I recommend this pro
Very happy with the work and the price.

Kim V.
Jun 2020
5.0
Door Service, Framing Service
Yes, I recommend this pro
$370
All work done by Chesapeake Roofing, Windows and Siding over the years has been excellent. Kurt and his team are professionals who offer very competitive pricing and the highest quality of service. We highly recommend this company!!

Paul D.
Jun 2020
5.0
Roofing
Yes, I recommend this pro
Prompt response to our call, competitive price, finished on time, and amazing clean up of all debris. This company has done all of our windows, siding, and roofs. I don't even call anyone else anymore!!!

Gary M.
Jun 2020
5.0
Door Service, General Remodeling
Yes, I recommend this pro
Great! Salesman was very knowledgeable, made recommendations, kept in touch, and made changes we made during the process. He went the extra mile to get exactly the same color as our shutters. The installation crew called ahead of time, arrived on time, and took care of everything that was needed. They did an exceptional job and left the job site perfectly cleaned up. Would use Chesapeake Roofing and Siding again to replace windows.

William F.
May 2020
5.0
Gutter Repair and Replacement
Yes, I recommend this pro
$2,178
Did not realize Chesapeake uses a subcontractor to install gutter guards. The team did a great job and worked diligently. I was disappointed that they did not blow the debris off my decks that came out of the gutters. My only concern was one of the workers had their family show up at my house while the work was still being performed. One person even walked their dog around my yard. I was okay with this but I am afraid another owner won't be so understanding.

Nancy K.
Apr 2020
5.0
Roofing, Gutter Repair and Replacement + 1 more
Yes, I recommend this pro
Initially I hired them to do my gutters as their price was very competitive and they had good ratings. They came out on time and did a fine job. As a result when I needed some shingles repaired on my aging roof I called them. They gave me a very fair quote, came out and did an excellent job and provided extraordinary customer service to boot. Highly recommend.

Ryan G.
Feb 2020
5.0
Roofing
Yes, I recommend this pro
$12,000
The entire experience with Chesapeake Roofing was great. I had a leak and had 4 roofing companies come out to provide estimates. My experience with all of them was good, but Chesapeake Roofing won the contract because of my interaction with Jack and Kurt. When I first noticed the leak I reached out to Chesapeake Roofing and received a return call within minutes of my inquiry. I was hoping for a repair, but none were successful at stopping the leak. When I finally resigned to the fact that I needed a new roof I reached out to Chesapeake Roofing again and the next day Jack was onsite with his friendly companion K-9 to inspect the roof. Jack helped me understand their process fully, worked with me on pricing, and was able to schedule the replacement the very next week. This was a relief given the leak. On the day the roof was replaced the crew arrived on time and had the entire project completed by midday. Jack even came by during the install to check on things. Per their policy and my instruction, they tarped around the house to protect my bushes, siding, deck, and other valued items. When I returned later that day there was no evidence that anyone had been there except for the beautiful new roof that was installed. The house has two additions and two valleys, making it more complex than a standard roof. Jack checked in once the work was completed and has followed up promptly with questions I have had. The best part... no more leak! I would highly recommend Chesapeake Roofing. Very competitive pricing, quality work, and without question the best customer service I have experienced from a contractor. Thanks guys!
Showing 1-25 of 97

Licensing

Bonded

Insured

Licensed*

Trade License Number

36354

Trade License Expiration

09/13/2025

State Contractor License Requirements

All statements concerning insurance, licenses, and bonds are informational only, and are self-reported. Since insurance, licenses and bonds can expire and can be cancelled, homeowners should always check such information for themselves. To find more licensing information for your state, visit our Find Licensing Requirements page.

*Contact business to see additional licenses.

FAQ

CHESAPEAKE ROOFING WINDOWS & SIDING is currently rated 4.9 overall out of 5.

Monday: 7:30 AM - 10:00 PM Tuesday: 7:30 AM - 10:00 PM Wednesday: 7:30 AM - 10:00 PM Thursday: 7:30 AM - 10:00 PM Friday: 7:30 AM - 10:00 PM Saturday: 7:30 AM - 10:00 PM Sunday: 7:30 AM - 10:00 PM

CHESAPEAKE ROOFING WINDOWS & SIDING accepts the following forms of payment: Financing Available, Check, CreditCard

Yes, CHESAPEAKE ROOFING WINDOWS & SIDING offers free project estimates.

Yes, CHESAPEAKE ROOFING WINDOWS & SIDING offers eco-friendly accreditations.

Yes, CHESAPEAKE ROOFING WINDOWS & SIDING offers a 2% senior discount.

No, CHESAPEAKE ROOFING WINDOWS & SIDING does not offer emergency services.

Yes, CHESAPEAKE ROOFING WINDOWS & SIDING offers warranties.

CHESAPEAKE ROOFING WINDOWS & SIDING offers the following services: ROOFING, WINDOWS, DOORS, VINYL SIDING, HARDIE SIDING, GUTTERS, AND GUTTER GUARDS.