Pleasant Bay Home Improvement

Charles Gallagher has been putting siding, windows and roofs on Cape Cod houses since 1984 — 42 years, by the company's own count — running Pleasant Bay Home Improvement out of South Orleans as a sole proprietorship. The company says the work stays in-house: its own employees, no subcontractors. The territory it claims runs across the lower and outer Cape — Harwich, Dennis, Brewster, Chatham, Orleans, Wellfleet and Eastham — and the job list follows the outside of the house: siding, roofing, window replacement, decks, gutters and carpentry, with kitchen and bathroom remodeling and additions alongside. A Porch listing for the same South Orleans address advertises aluminum siding installation and repair. On Google the company holds 4.5 stars across four ratings. A homeowner writing in November 2024 had used Pleasant Bay for a number of years across multiple projects on their house, and described estimates the company stuck to and permitting it handled for them; they praised the quality of the work. The Better Business Bureau grades the business A+. One thing to check yourself first: the Massachusetts registry lists home improvement contractor registration #119269 — the same number the company's site cites, with Gallagher as holder of record — as expired. The site also cites Construction Supervisor License #105134, and the company says it belongs to the Cape Cod Chamber of Commerce. For a Cape homeowner who wants an exterior crew with four decades in the same towns and employees rather than subs, Gallagher's shop is that kind of outfit. Before anything starts, ask him to show current registration and insurance, get the scope and price in writing, and confirm who pulls the permits on your job.