What does a roof replacement cost in Greater Boston?
Typical Greater Boston range for this kind of work, from regional averages — not a quote from Care Free Homes, Inc.. Use it to sanity-check bids, then get the real number in writing.
A square is 100 sq ft of roof surface — bigger than the floor plan because of pitch and overhangs.
— customers credit specific installers and foremen by name
Daily cleanup — repeated praise for tidy sites and cleared debris
Repeat hires — homeowners return for third and fourth projects
Warranty follow-through — returned years later to fix damaged siding
Fast roof work — one full replacement finished in a single day
Verified registration — Massachusetts home improvement contractor registration is active
Estimate-stage contact — a 2023 reviewer described curt texts and no callback
Property care — a 2026 window job damaged a neighbour's mailbox, since resolved
Forty-one reviews have landed in the last six months, and not one of them is critical. That is the through-line for Care Free Homes, a Fairhaven company homeowners on the South Coast and Cape call when the outside of the house needs replacing — roofs, siding, windows and doors, gutters, decks and porches, with additions and new home construction on its Better Business Bureau service list.
The written history runs deep: 210 reviews since 2021 across eleven different sites. Google sits at 4.9 from 225 ratings, Houzz at 4.9 from 31, while Porch (4.7 from 405) and HomeAdvisor (4.7 from 121) land slightly lower. What actually repeats in the writing is more useful than the averages, though — customers name the people who did the work. Paul, Zach and Sanchez on roofs; Danny and Jayden on windows; Jay on a sliding-door replacement in Plymouth that turned out more complicated than anyone expected; Dana Sr. calling ahead about who would be on site which day. Cleanup comes up almost as often as craftsmanship, including one crew that swept for stray nails with a magnet after working around a solar-panel removal.
The other pattern worth noticing is people coming back. One homeowner wrote in 2026 about a third project with the company, another was signing up for a fourth, and a third had done three. A homeowner whose siding was damaged years after installation described the company returning to assess the cause, suggest a fix so it would not recur, and replace the panels.
The dissent is narrow and old, but real. In a March 2023 one-star review, a homeowner never got past the estimate: they described a curt message from a salesperson when they did not reply quickly enough, a second one on a follow-up quote, and a manager who never returned their call. On a 2026 window job, a reviewer mentioned a neighbor's mailbox being damaged, and said the company sorted it out. If you hire them, pin down early who your single point of contact is, since reviewers name a lot of different estimators and foremen.
Its Massachusetts home improvement contractor registration is active, and its BBB page carries an A+ with accreditation dating back to 1993. A 2021 TurnTo10 story described its annual "New Year, New Roof" giveaway, and a local nonprofit has written about being a finalist for it.
The right call for a whole-exterior job — a roof plus siding plus windows in one pass — rather than a one-off repair. Confirm the crew and the point of contact when you sign.
Heard around town
News & the web
New Bedford hospital greeter gifted new roofFeb 12, 2021
“For the past six years, Care Free Homes Inc., a local company that provides home improvement and construction services, has been hosting "New Year, New Roof."”
LifeStream Chosen as a Finalist in the New Roof Giveaway LifeStream, Inc.
“In honor of the 10th Anniversary of the New Roof Giveaway, Care Free Homes, in partnership with GAF Roofing, has made this year’s contest exclusively for local nonprofit organizations and we are honored to be one of three in the running for this amazing gift.”
I had several smaller jobs over the years, rebuilding steps, and vynil siding on my home installed. The price was reasonable, and work completed quickly and carefully. They honor their warranties, and do any covered repairs if needed. I am satisfied with their service !
The salesman arrived timely to provide a quote for the job. The contractor also arrived timely to take the measurements. When the products arrived the appointment was set up. The crew arrived when promised and the work began. Both members of the crew worked efficiently. The job to replace a slider and 2 rolling windows was completed in 2 days. The crew cleaned up after the job and left the property in good order. They did an excellent job. Will definitely call them again for future work.
Was wonderful working with Dana and the team on our deck project. Just a first-rate company and my best experience ever working with a contractor. The price was extremely reasonable, totally transparent process, quick response times, and incredibly high quality work. I will use Care Free Homes for all my future contracting needs, and can’t recommend them more highly!
Care Free Sided our house a number of years ago, and we were very satisfied. Subsequently one side of the house was damaged through no one's fault. Care Free came out to assess, and suggested how to remediate the issue so it wouldn't happen again. Once that was taken care of, they came out and replaced the damaged siding. The guys were professional, quick and it looks great.
General Contractor / RemodelingCarpentryasphalt shingle roofingcedar shingle sidingexterior door installationgutter installationdeck constructionporch constructionsunroom construction