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Water was leaking through the roof into the house after a big storm when one recent customer called The Roof Boss. That customer reached Billy on the first call, and he came over the same day. The company says on its website that Billy spent most of his career with large roofing companies before branching out on his own, and it claims over 20 years of hands-on roofing experience. Its website names North Branford as its service area. On Google it shows 5 stars from 26 ratings. A recent customer with a hole in the roof said Bill from Roof Boss was the only one to call and check up on them while they waited on the insurance company. A recent customer said Billy and his team show up at 7am, stay until 6pm and clean up every night. A 2026 customer said that after three different roofing companies failed to complete a hail and wind damage claim, Billy got the claim paid and completed a new roof. A 2026 customer with ice dams causing dripping in the walls said Billy came out the next day, gave options for clearing the whole roof or just the problem spot, and did the work for a reasonable price. A 2025 customer said Billy and his team installed gutter guards, wrapped several windows and repaired windowsills, and that his team was on time.
Roof Boss is an excellent group of professionals. They did what they said they would do. I had a hole in my roof had to wait for the insurance company to cover the cost. Took way too long. Bill from Roof Boss was the only guy to call and check up on me. I can't say enough good things about the company. Very professional. Cleaned up. Just a great experience. Thank you Roof Boss!
I reached out after a big storm and water was leaking through the roof into the house. I reached Billy on my first call and he came over the same day to resolve the issue. His fast responsiveness saved us more damage from the leak. Will definitely be contacting again for any other roof needs. Highly recommend!
Amazing experience. Extremely professional. Billy and his team show up every morning at 7am ready to work and stay until 6pm. They are all hard working and friendly. They clean up every night and make sure that the home owner is happy with their work. Wold recommend them for all your roofing and siding needs!
Billy was awesome to work with. Very responsive and professional
I highly recommend The Roof Boss! Very professional and high quality work. They have done new construction roofing and storm repair for us. We are extremely happy with their work.
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1 change recorded — last scanned Oct 13, 2026.
Typical your area range for this kind of work, from regional averages — not a quote from THE ROOF BOSS. 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
Chimney leak sealed with a dam, lead barrier and copper flashing5.0
New roof through insurance for just the deductible5.0
Drone photos of the roof shown before replacing5.0
Insurance-deadline roof redone within two weeks5.0
143 years in business3.5
Flat roof replaced and the leaks stopped3.3
Complete roof replaced in 1.5 days3.9