The Aiello Roofing Company

Old roof off, new roof on, grounds cleaned up, all in one day: that is how a recent customer described working with Chris Aiello and his father Kenny. The Aiello Roofing Company says it has served homeowners in Western Connecticut since the early 1980s, beginning with Kenny Aiello's own work, and that it is now led by Christopher Aiello alongside his brother Andrew. It lists New Milford, Sherman, Kent, Brookfield and New Fairfield among the towns it serves, and its BBB page shows an A+ grade. That same one-day job included swapping out an old skylight, and some interior skylight trim was damaged along the way; the customer said they came back within a couple of days and took care of it to their satisfaction. A recent customer texted Chris a photo of a broken downspout on a Saturday, got a reply Monday morning, and came home after work to find it fixed. A recent customer said Kenny repaired the roof after a contractor removed an old stove pipe, and was prompt again with an unrelated leak found a few days later. A recent customer had the roof replaced and a two-tiered deck replaced as well. A recent customer called the repairs after tree damage to the roof quick and well priced. A 2026 customer with an ice-dam leak said Chris sent a crew within hours. A 2025 customer said a leak turned out to be mostly the chimney, which Aiello Roofing came back and sealed, and the ceiling stayed dry through a long torrential rain. A 2025 customer said a hole a tree branch punched in the roof was repaired within an hour. A 2025 customer said Chris Aiello had done minor roof repairs and a large window replacement before handling a roof replacement. A 2024 customer had a complete roof and siding makeover. A 2023 customer from Sherman, CT said the new roof went on within 6 hours, and that three different people later stopped their cars to ask who did it. Connecticut lists its home improvement contractor registration, HIC.0641306, as active, held by The Aiello Roofing & Remodeling Company.