# Pleasant Bay Home Improvement **Trade:** Windows / Siding / Gutters · **Phone:** (508) 237-5177 · **Website:** http://www.pleasantbaysiding.com/ · **Languages:** English **Rating: 3.6/5** (low confidence) — from 1 reviews across 9 sources. ## The honest read 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. **Strengths:** - Estimates that hold — a 2024 repeat customer said quotes were always adhered to - Permitting handled — same 2024 review credited them with all the permits - Own employees only — company states it does not use subcontractors - A+ BBB grade — profile lists 42 years under one owner since 1984 **Concerns:** - Expired HIC registration — state registry shows license 119269 expired - Unverified supervisor license — CSL #105134 appears only on their own site - Thin written history — one customer account on file, from 2024 **Where sources disagree:** - Porch lists the business as 'over 25 years in business' while its BBB profile and its own site say 1984 (42 years). ## Claims & citations Every claim below is backed by real evidence rows — uncited claims are dropped in code before publication. - Massachusetts home improvement contractor registration 119269 is registry-verified expired, with Charles Gallagher as the holder of record _(confidence: high)_ - [State License Registry](https://contractorhub.mass.gov/s/hic-contractor-search) — “MA hic license 119269 registry-verified expired — registry holder of record: CHARLES GALLAGHER” - BBB grades the business A+, though it is not a BBB-accredited business _(confidence: high)_ - [Better Business Bureau](https://www.bbb.org/us/ma/south-orleans/profile/siding-contractors/pleasant-bay-home-improvement-0021-111244) — “Better Business Bureau grade: A+” - [Better Business Bureau](https://www.bbb.org/us/ma/south-orleans/profile/siding-contractors/pleasant-bay-home-improvement-0021-111244) — “BBB profile for Pleasant Bay Home Improvement (PO Box 830, South Orleans, MA), rated A+ by BBB but NOT a BBB-accredited business, in busines…” - BBB lists a sole proprietorship owned by Charles Gallagher, in business since 1984, based at PO Box 830, South Orleans _(confidence: high)_ - [Better Business Bureau](https://www.bbb.org/us/ma/south-orleans/profile/siding-contractors/pleasant-bay-home-improvement-0021-111244) — “BBB profile for Pleasant Bay Home Improvement (PO Box 830, South Orleans, MA), rated A+ by BBB but NOT a BBB-accredited business, in busines…” - A November 2024 Google reviewer described using the company across multiple projects over several years, with estimates adhered to and permitting handled _(confidence: medium)_ - [Google Reviews](https://www.google.com/maps/reviews/data=!4m8!14m7!1m6!2m5!1sChZDSUhNMG9nS0VJQ0FnSUMzb28zY1hnEAE!2m1!1s0x0:0x50c5f62cac664453!3m1!1s2@1:CIHM0ogKEICAgIC3oo3cXg%7C%7C?hl=en) — “5★ We have been using Pleasant Bay Home Improvements for a number of years on multiple projects on our home. They are very professional. The…” - The company says it uses no subcontractors and that all work is done by its own employees _(confidence: medium)_ - [Official Website](http://www.pleasantbaysiding.com) — “Ownership (self-reported): Founded and run by Charles Gallagher since 1984; the company states it does not use subcontractors and all work i…” - The company's own site lists Construction Supervisor License #105134, a number not verified against any registry _(confidence: medium)_ - [Official Website](http://www.pleasantbaysiding.com) — “Self-reported license/registration number (NOT verified against any registry): Construction Supervisor License #105134” - Siding, roofing, window replacement, decks, carpentry and additions _(confidence: high)_ - [Official Website](http://www.pleasantbaysiding.com) — “A Cape Cod home improvement contractor based in South Orleans, MA, offering siding, roofing, window replacement, kitchen and bathroom remode…” - [Better Business Bureau](https://www.bbb.org/us/ma/south-orleans/profile/siding-contractors/pleasant-bay-home-improvement-0021-111244) — “Services offered (Better Business Bureau): siding, roofing, window replacement, deck design, carpentry, additions” - Stated service area covers Harwich, Dennis, Brewster, Chatham, Orleans, Wellfleet and Eastham _(confidence: medium)_ - [Official Website](http://www.pleasantbaysiding.com) — “Stated service area (self-reported): Harwich, Dennis, Brewster, Chatham, Orleans, Wellfleet, Eastham” - Google shows 4.5 stars from 4 ratings _(confidence: low)_ - [Google](https://www.google.com/maps/search/?api=1&query=Pleasant%20Bay%20Home%20Improvement&query_place_id=ChIJaWGgc6xr-4kRU0RmrCz2xVA) — “Google: 4.5★ from 4 ratings” - Founded in 1984 by Charles Gallagher after years apprenticing with a local contractor, per the company's own account _(confidence: medium)_ - [Official Website](http://www.pleasantbaysiding.com) — “Company history (self-reported): Founded in 1984 by Charles Gallagher, who opened the business after years apprenticing with a local contrac…” - [Official Website](http://www.pleasantbaysiding.com) — “Self-reported 42 years in business” - Specializes in Windows / Siding / Gutters _(confidence: high)_ - [Official Website](http://www.pleasantbaysiding.com) — “A Cape Cod home improvement contractor based in South Orleans, MA, offering siding, roofing, window replacement, kitchen and bathroom remode…” - [Better Business Bureau](https://www.bbb.org/us/ma/south-orleans/profile/siding-contractors/pleasant-bay-home-improvement-0021-111244) — “Services offered (Better Business Bureau): siding, roofing, window replacement, deck design, carpentry, additions” - Specializes in Roofing _(confidence: high)_ - [Official Website](http://www.pleasantbaysiding.com) — “A Cape Cod home improvement contractor based in South Orleans, MA, offering siding, roofing, window replacement, kitchen and bathroom remode…” - [Better Business Bureau](https://www.bbb.org/us/ma/south-orleans/profile/siding-contractors/pleasant-bay-home-improvement-0021-111244) — “Services offered (Better Business Bureau): siding, roofing, window replacement, deck design, carpentry, additions” - Also offers Carpentry _(confidence: medium)_ - [Official Website](http://www.pleasantbaysiding.com) — “A Cape Cod home improvement contractor based in South Orleans, MA, offering siding, roofing, window replacement, kitchen and bathroom remode…” - [Better Business Bureau](https://www.bbb.org/us/ma/south-orleans/profile/siding-contractors/pleasant-bay-home-improvement-0021-111244) — “Services offered (Better Business Bureau): siding, roofing, window replacement, deck design, carpentry, additions” - Also offers General Contractor / Remodeling _(confidence: medium)_ - [Official Website](http://www.pleasantbaysiding.com) — “A Cape Cod home improvement contractor based in South Orleans, MA, offering siding, roofing, window replacement, kitchen and bathroom remode…” - [Better Business Bureau](https://www.bbb.org/us/ma/south-orleans/profile/siding-contractors/pleasant-bay-home-improvement-0021-111244) — “Services offered (Better Business Bureau): siding, roofing, window replacement, deck design, carpentry, additions” - Also offers Bathroom Remodel _(confidence: medium)_ - [Official Website](http://www.pleasantbaysiding.com) — “A Cape Cod home improvement contractor based in South Orleans, MA, offering siding, roofing, window replacement, kitchen and bathroom remode…” - [Porch](https://pro.porch.com/south-orleans-ma/roofers/pleasant-bay-siding-and-home-improvement/pp) — “Services offered (Porch): Aluminum Siding Installation, Aluminum Siding Repair, Bathroom Design, Bathroom Remodeling, Bathroom Remodeling - …” - Also offers Kitchen Remodel _(confidence: low)_ - [Official Website](http://www.pleasantbaysiding.com) — “A Cape Cod home improvement contractor based in South Orleans, MA, offering siding, roofing, window replacement, kitchen and bathroom remode…” ## License Status: **expired** (#119269, hic) — verified against the official MA state registry on 2026-08-24, never self-reported. Re-check at the official registry: https://contractorhub.mass.gov/s/hic-contractor-search ## Sources - [Google](https://www.google.com/maps/search/?api=1&query=Pleasant%20Bay%20Home%20Improvement&query_place_id=ChIJaWGgc6xr-4kRU0RmrCz2xVA): 4.5★ from 4 ratings - [Google Reviews](https://www.google.com/maps/search/?api=1&query=Pleasant%20Bay%20Home%20Improvement&query_place_id=ChIJaWGgc6xr-4kRU0RmrCz2xVA): Listed on this source - [Better Business Bureau](https://www.bbb.org/us/ma/south-orleans/profile/siding-contractors/pleasant-bay-home-improvement-0021-111244): Listed on this source - [Yelp](https://www.yelp.com/biz/pleasant-bay-homes-harwich): Listed on this source - [Official Website](http://www.pleasantbaysiding.com): 42 yrs in business · Self-reported profile and service details - [Houzz](https://www.houzz.com/professionals/home-builders/pleasant-bay-homes-pfvwus-pf~378387360): Listed on this source - [Procore Construction Network](https://network.procore.com/p/pleasant-bay-homes-inc-harwich): Listed on this source - [Exa](https://pro.porch.com/pleasant-hill-ca/general-contractors/sandl-remodeling-and-design-inc/pp): 0 web mentions across the open web (each linked to its source) - [Porch](https://pro.porch.com/south-orleans-ma/roofers/pleasant-bay-siding-and-home-improvement/pp): Listed on this source ## Recent reviews - **5/5 · Google Reviews · David Van Ness · 2024-11-04**: We have been using Pleasant Bay Home Improvements for a number of years on multiple projects on our home. They are very professional. They provide an estimate which they have always adhered to, they’ve dealt with all the permitting and the quality of their work is excellent. The crew is pleasant and… --- Data freshness: last scanned 2026-08-22T05:07:09.800Z. Cite as: Pleasant Bay Home Improvement — Tavlee (https://tavlee.com/contractor/pleasant-bay-home-improvement) Source: https://tavlee.com/contractor/pleasant-bay-home-improvement