Care Free Homes, Inc.

Care Free Homes has been putting roofs, siding and windows on homes in Fairhaven and the South Coast since the Blizzard of '78, when family members Wayne Edwards Sr. and Dana Pickup Sr. started the business door to door — the company says it's now run by a third generation of the Pickup family, with Nathan Pickup Sr., a West Point graduate and five-year Army veteran, and Dana Pickup Jr. as co-owners. Its Massachusetts home improvement contractor registration is active, and it has held a Better Business Bureau A+ rating and accreditation since 1993. The written record backs that up at scale: 210 reviews since 2021 across Google, Angi, Houzz and HomeAdvisor, running 4.9 stars on Google (225 ratings) and Houzz (31 ratings) and 4.7 on Porch and HomeAdvisor. Roofing, siding and window replacement are the jobs that come up over and over, with the same crew names recurring across separate projects — Paul, Zach and Sanchez on more than one roof, Bob Lima quoting decks and full exterior remodels, Dana Sr. and Dana Jr. coordinating scheduling. Several reviewers describe using the company for a third or fourth project on the same house, and in a 2025 review one customer described a crew tracking down squirrel damage that a solar-panel removal had left hidden under the roof deck. The company also runs an annual "New Year, New Roof" giveaway with GAF Roofing for local nonprofits — a 2021 local news story said it was already in its sixth year. The last six months brought 38 reviews with zero negative ones, and the pattern holds: crews show up on schedule, clean up daily, and stay in touch through the job — deck and addition work, including a custom handicap ramp, gets the same treatment as roofing and siding. The one real complaint on file is a 2023 review from someone who never became a customer, describing a rude message from a salesman after being slow to reply about an estimate. Care Free Homes is a strong call for a full exterior remodel — roof, siding, windows and gutters together — or for a homeowner who wants a contractor to keep coming back to for the next project; worth confirming upfront how quickly the sales team follows up if a quote request needs a second look.