Cheshire Roofing, LLC

The only one or two-star review we hold for Cheshire Roofing, LLC.

• 1 out of 5Andrew Ashworth2 years ago

  Developed a dripping leak in my living room during a recent storm. I am an Airline Pilot so being away from home frequently, my wife is left to handle these stressful situations. She called Cheshire Roofing due to the great reviews they have on our local community Facebook page, and they sent a guy out the very next day to assess the problem. When he arrived, he took one look at the leak inside the house and told my wife he would 'return later in the week with his ladders'. I waited a week and left leaving multiple voicemails with no response. The following weekend I tarped the roof myself before a second rainstorm hit, and moved onto another local company that treated me as a priority. Not only was Cheshire roofing too busy to handle my issue, they didn't even extend us the curtesy of returning our calls. I would not recommend this company.

  Reply from the business

  My apologies for the miscommunication.

• roof replacement8
• fair pricing6
• cleanup3
• responsiveness3
• shingles2
• thorough quote2
• professional crew2
• efficient work2
• easy process2
• workmanship2

14 more of the 19 reviews we hold text for, most recent first. We do not hold every review Google has.

• 5 out of 5Michael Gibeau5 days ago

  Had siding, roof repair, and a roof replacement done by Cheshire Roofing. They were absolutely great. Very professional and timely. They also did a phenomenal job cleaning up after.

  Reply from the business

  Michael, thank you for the review and the job.

• 5 out of 5Neil Bradleya month ago

  Having leaks in your roof is like having leaks in your boat - you get that same dreadful, sinking feeling. We chose Cheshire Roofing to replace our roof because their proposal was competitively priced, our neighbors recommended them, and they were upfront with us about potential added costs. They were the only roofing company to tell us the bad news up front – we could expect to replace as many as 20 sheets of plywood based on their findings. Their honesty was reassuring, and they gained our trust immediately. The installation crew was punctual, worked hard, finished the job on time, and cleaned up all debris. I highly recommend them.

  Reply from the business

  Thank you Neil, thanks for letting us earn your trust.

• 5 out of 5glenn paddocka month ago

  We had an excellent experience with cheshire roofing today. They are professional, courteous and excellent with their cleanup. They searched around to make sure that they picked up all the nails that might have fallen from the roof . I would highly recommend Steve and his crew. The job was finished in one day, on time.

  Reply from the business

  Thank you Glen and thank you for sharing the pictures.

• 5 out of 5Ravi Shankar4 months ago

  I recently hired Cheshire Roofing, and I am extremely impressed with their service. From the initial quote to the final inspection, they were very professional, responsive, and easy to work with. …

  Google cut this review short. The full text is on their Google profile.

  Reply from the business

  Thank you very much Ravi.

• 5 out of 5Maria Bradley11 months ago

  Cheshire Roofing came out and did the job quickly and effectively. Steve did a great job he was professional, thorough, and made sure everything was done right. I’m very happy with their service and would definitely recommend them.

  Reply from the business

  Thank you, I appreciate the recommendation.

• 5 out of 5Ryan Kregera year ago

  I was referred to Steve and Dennis through my realtor, purchasing a house that had some roof issues (it needed a new one, had three different types of roofing, and a previous roofer who did some 'repair' work.) They came out, quoted me, …

  Google cut this review short. The full text is on their Google profile.

  Reply from the business

  Ryan, thank you for putting your trust in us. Appreciate the kind words, I will pass it on to the crew.

• 5 out of 5Mark Secondoa year ago

  The team was on time and offered plenty of financing options. Honest and hard-working company.

  Reply from the business

  Thank you Mark.

• 5 out of 5Jake Freezea year ago

  I'm thrilled with the job done by Cheshire Roofing. The whole process was transparent and all my questions were answered. They made it really easy for me.

  Reply from the business

  Thanks for the feedback.

• 5 out of 5Steve Ackleya year ago

  Very happy with this group. We had a kitchen renovation going on and found we had a major leak from the chimney. Called them and they were there the next day to Address the issue. I then had them come in to replace our roof. The team he send were amazing— worked hard, cleaned up after every day and reasonably priced

  Reply from the business

  Thanks Steve. We appreciate the kind words, happy to help.

• 5 out of 5Michael Cavaliere Jr.2 years ago

  Very pleased! They repaired my leaking bathroom vent and shingles around it. Also noticed my chimney was falling apart. They then referred me to a great mason (Freddy Tomori) who repaired my chimney and then Cheshire roofing reflashed the chimney and shingles around the chimney. All done at a very good price. My next roof will be put on by CHESHIRE ROOFING.

  Reply from the business

  Thank you Michael, we appreciate the kind words and 5 star rating.

• 5 out of 5Milan Boneta2 years ago

  I developed a leak at my roof vents. I called Steve and he responded quickly to meet and evaluate the issue. He provided a fair price and had his crew here the following day to make the repair. They were here when he said they would be, he …

  Google cut this review short. The full text is on their Google profile.

  Reply from the business

  Thank you very much for the positive review.

• 5 out of 5Susan Lofton2 years ago

  We live in Hamden CT having moved here from Wisconsin last year. Early on we realized we had a roof and a gutter leak. Based on Google reviews, we contacted Cheshire Roofing and met Steve who we quickly learned has encyclopedic knowledge …

  Google cut this review short. The full text is on their Google profile.

  Reply from the business

  Thank you, Susan, it was our pleasure.

• 5 out of 5Jennifer Downey2 years ago

  Fast, with reasonable prices

  Reply from the business

  Thank you Jennifer!

• 5 out of 5Zentek Farms3 years ago

  Steve and his crew did a great job on my new roof , from start to finish . Everything was clean after they finished as well. Thanks again Steve !

  Reply from the business

  Thank you, Joe, much appreciated!

Need a trusted roofing contractor in serving all of Connecticut? Cheshire Roofing, LLC has provided professional roofing and siding services throughout Connecticut for more than 24 years. Our experienced team offers roof inspections, roof repairs, roof replacements, siding installation, and storm-damage assessments for residential properties. As a GAF Certified roofing contractor with an A+ BBB rating, we are committed to quality workmanship, dependable service, and long-lasting results. Call Cheshire Roofing, LLC to schedule your free roof inspection today. Serving communities throughout Connecticut.Aug 1, 2026Call now

• Licensed

  “…We are fully licensed and insured and can provide…”

• States years in business

  “…WELCOME TO CHESHIRE ROOFING, LLC Over 22 years of experience serving Connecticut.…”

• Mentions the BBB

  “…your project.” Check us out on The Better Business Bureau, we are a company in great standing.…”

Their site also states: insured.