Pleasant Bay Home Improvement

Forty-two years in one trade, on one stretch of coast, under one owner. Charles Gallagher started Pleasant Bay Home Improvement in South Orleans in 1984 after apprenticing with a local contractor, and the company says he still runs it — a sole proprietorship, according to its BBB profile, working Harwich, Dennis, Brewster, Chatham, Orleans, Wellfleet and Eastham. The work is Cape exterior work first: siding, roofing, window replacement, decks and carpentry, with additions and kitchen and bath remodeling alongside. One unusual detail from the company's own account is worth asking about, because it shapes who actually shows up: it states it does not use subcontractors, and that every job is done by its own employees. The written history is thin — one customer account on file, from November 2024, but a useful one. That homeowner described using the company across multiple projects over a number of years and singled out the two things that go wrong most often on Cape jobs: the estimate held, and the permitting was handled for them. Google sits at 4.5 stars from 4 ratings. The BBB grades the business A+, though it is not a BBB-accredited business and its page carries no review rating. The thing to settle before signing anything: Massachusetts home improvement contractor registration 119269 is in the state registry under Charles Gallagher, and it comes back expired. The company's own site lists that same number, plus a Construction Supervisor License #105134 that we did not verify against a registry. Ask where both stand today — HIC registration is what backs a homeowner's access to the state's Guaranty Fund if a job goes sideways. A good fit if you want a long-established Orleans-area outfit doing its own siding and roofing work rather than handing it to a crew you have never met. Confirm the registration status and get current insurance certificates before the first delivery lands.