Verified record
City Roofing & Siding says it was founded in 1958 and describes itself as a third-generation, family-owned home improvement company doing roofing, siding and window work. Its website lists a service area that includes Middletown, Cromwell, Glastonbury, Berlin and Rocky Hill. A 2025 customer said the company took a neglected old drafty home through a complete renovation: a new roof, windows, doors, gutters and siding. That customer said meeting with Matt simplified the project into a step-by-step process, and in that 2025 review praised the courtesy of the crew while it was on site. A 2025 customer from Cheshire said City Roofing had installed the porch's rolled roofing some 20 years earlier. When it developed a leak after heavy rain, that 2025 reviewer said Matt made temporary repairs on two occasions at no cost, and in late April the team finished the job in 4-5 hours with a thorough clean up. A 2025 customer said they came out promptly, identified and fixed the issue, and called the next day to check how it held up in the rain. A 2024 customer said they messaged Matt early on a Saturday morning about a very small job and he came out the same day. Its Connecticut home improvement contractor registration, HIC.0532021, is active on the state registry, held by City Roofing & Siding Co Inc.
This was by far the best experience my family and I have ever had with any contractor. The process from step one to completion was extremely thorough with great attention to detail. We were very hesitant on, performing such extreme home renovations to a neglected old drafty home, but after meeting with Matt at City Roofing siding, it was simplified as a step-by-step process, and we were very confident in what he presented. We had a complete renovation. New roof, windows, doors, gutters, and siding. City Roofing and siding completely transformed our home into the most beautiful home in our neighborhood. The pride we feel when driving up the street and looking at it is indescribable . We are complimented every single day by People walking or driving by. The outstanding work and craftsmanship by City Roofing and siding has exceeded all our expectations. I must say, we were extremely impressed by the courtesy, professionalism and downright politeness of their entire crew every moment they were on site. I have to say it again this was truly the best experience we’ve had. We only wish they can do our complete interior next!!
I had a great experience with Matt and City Roofing. They came out promptly and quickly identified/fixed the issue. I also appreciated the follow-up call the next day to check on how it held up in the rain. Highly recommend.
Matt from city roofing was very professional And very knowledgeable ! Will definitely hire him again for our next project!
Some 20 years after City Roofing installation, our porch’s rolled roofing developed a nuisance leak this winter (2023) after heavy rain. Matt explained we were well beyond the expected life for rolled roofing and made temporary repairs on 2 occasions (at no cost). He explained we’d need to wait for temps to reach 40+,degrees to replace the rolled roofing. In late April the team finished the job in 4-5 hours, with a thorough clean up . This is my second experience with City Roofing and I highly recommend Matt and his team. Bill Walsh Cheshire
Second time Matt came out to see a problem with my roof. Offered to fix it without hesitation. Very honest company.
Specializes in
Also offers
Service area
1 change recorded — last scanned Oct 30, 2026.
Typical Connecticut range for this kind of work, from regional averages — not a quote from City Roofing & Siding. Use it to sanity-check bids, then get the real number in writing.
Estimated range
$3,750 – $10,300
Typical exterior project around $7,050
Languages
Languages
Ownership
Certified attributes are verified against the public registry. Others are the business's own statement.
Ownership
Certified attributes are verified against the public registry. Others are the business's own statement.
One-day roof replacements5.0
Estimate matched the final cost5.0
27 windows installed in a single day4.5
