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Big Dawg Home Improvements works on roofs out of South Windsor, and its website says it is in its 6th year providing Connecticut property owners with roof replacements, roof repairs, gutter systems, vinyl siding and windows. Its Connecticut home improvement contractor registration, HIC.0658845, is active on the state registry, held by Big Dawg Home Improvements LLC. A recent Google customer said Big Dawg repaired their roof the next day. A recent customer wrote that the company installed a new roof in one day and never seemed to be trying to upsell. A recent siding customer said the worksite was left spotless at the end of every day and the final cost was exactly as quoted. After a tree fell in a recent customer's yard, that customer said Matthew and his team came in and cleaned everything up. A 2026 customer described an ice dam with water leaking into the house and said Matt came out the very next day, first thing. A 2025 customer wrote that Matthew did a full roof assessment with drone photos and submitted the paperwork to their insurance company directly. A 2025 reviewer said Big Dawg replaced the roof of Rockville United Methodist Church on Grove Street. A 2025 customer said the crew came out the same day to clean gutters that had trees growing in them, and finished in an hour. A 2024 customer said Matt replaced deteriorating boards and installed lead flashing around the chimney when the company replaced their roof. A 2023 customer said the team used a magnet multiple times to pick up nails during a roof replacement. On Reddit in 2024, a commenter recommended the South Windsor company.
“Big Dawg out of South Windsor. I just wrote a Google review under name: Rob Short answer is they are excellent. 5 stars all day long”
“https://bigdawghomeimprovements.com/ in South Windsor. Great company, great owner, great work. Highly recommend.”
“Matthew McKenna of Big Dawg Home Improvements led the project, which took about a week to build following a month and a half of design, permitting, and prep.”
“McKenna’s business specializes in roofing, siding, gutters and windows. While his business is located out of South Windsor, McKenna travels all over Connecticut servicing homes and businesses.”
Extremely responsive! Dawg was able to repair my roof the next day, which was very comforting. Highly recommend!
High quality work from great people
It was a pleasure working with Matthew on my home improvement project with my roof. We emphasize the importance of completing the work quickly and thoroughly and him and his team did an amazing job the next day. We couldn’t be happier with the results and we will use him for our future gutter project. His quote was exceptionally priced.
Matthew and his team provided truly outstanding service! A tree fell in my yard, and they came in, cleaned everything up, and did an amazing job. They were prompt, professional, reliable, and delivered the highest quality service. I highly recommend Big Dawg Home Improvements!!!
I couldn’t be happier with the decision to choose Big Dawg Home Improvement! They did an amazing job on our siding, and the entire process from start to finish was a breeze. Their work is truly impeccable, with a level of attention to detail that completely exceeded my expectations. Not only did they complete the job incredibly fast, but they also made sure the worksite was left spotless at the end of every day. There were no hidden fees or surprises—the final project cost was exactly as quoted. Shoutout to Matt, who was fantastic to work with. He kept me informed and updated throughout the entire project, which gave me total peace of mind. I highly recommend Big Dawg Home Improvement to anyone looking for a reliable, professional, and skilled contracting team!
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1 change recorded — last scanned Oct 29, 2026.
Typical your area range for this kind of work, from regional averages — not a quote from Big Dawg Home Improvements. Use it to sanity-check bids, then get the real number in writing.
A square is 100 sq ft of roof surface — bigger than the floor plan because of pitch and overhangs.
Estimated range
$9,000 – $18,600
Typical roofing project around $13,800
Leak response with James on site within 2 hours3.8
One-day roof replacements5.0
