O'Brien Home Services

O'Brien Home Services is a Holden, Massachusetts roofing contractor that's been run by Kenneth O'Brien since 1988 — its Massachusetts home improvement contractor registration is active and held in Ken's own name, and BBB has accredited the business with an A+ rating since 2012. People call for full reroofs, storm-damage repair, gutters, siding and skylights, and Ken is described as on site running the job himself rather than sending a crew alone. The reviews describe repeat business more than one-off jobs: one customer has used the company on three different properties across Massachusetts and New Hampshire, and another had Ken reroof their family home 15 years ago and came back for the same work recently. When a tree came down on one customer's house, Ken's crew had it tarped within 24 hours and went on to repair the broken rafters, replace the roof and install new gutters. Another customer called about snow and ice dams and had a crew on the roof within two hours. The one account worth weighing against that record is a 2022 Reddit post: a homeowner who hired the company for a full roof, rafter tails, soffits and gutters said the price was fair and the work went fast, but it took a while to get onto the schedule, and they kept finding nails and pieces of aluminum gutter in the yard for close to a year afterward. For a reroof or storm-damage call, the reviews point to a company where the owner personally runs the job start to finish. Given the one cleanup complaint, it's worth asking upfront how the crew handles job-site cleanup and confirming a start date before signing.