Why Choose CFH?

Care Free Homes, Inc. is a family-owned home improvement & construction company located in Fairhaven, Massachusetts.

An A+ member of the Better Business Bureau for over 25 years, we provide top-quality customer service, outstanding product warranties and guarantee all of our workmanship for a full 10 years. We are fully licensed and insured in Massachusetts and Rhode Island. Care Free Homes customers are served by the Pickup Family and our own team of qualified craftsmen.

The Care Free Homes, Inc. Family

Care Free Homes PresidentDana Pickup, Sr. was 23-years-old when he co-founded a small, home improvement company with his brother-in-law, Wayne Edwards. Since its founding in 1978, Care Free Homes, Inc. has evolved from a small roofing, siding, and window business to a full service, custom home improvement and construction company. It is now one of the largest, family-owned home improvement companies serving Cape Cod, Southeastern Massachusetts, and Rhode Island.  Although Wayne is no longer a partner, Dana and his two sons, Nathan and Dana Jr., now co-own the company and maintain the family commitment to quality craftsmanship and service.  Dana serves as president of Care Free Homes, Inc.  In his free time he can be found cheering for his seven grandchildren at various sporting events or enjoying an afternoon motorcycle ride with his wife, Joan.

Care Free Homes Vice PresidentNathan Pickup, Sr. graduated from Fairhaven High School before earning his bachelor’s degree from the United States Military Academy at West Point in 1997.  He was commissioned as an officer and served 5 years on active duty as an infantryman in the U.S. Army, deploying to both Bosnia and Afghanistan.  In 2002, Nathan returned home to work for the family business as a project manager and continued to serve as a company commander in the Massachusetts Army National Guard. Nate serves as Vice-President of Care Free Homes. He and his wife, Stephanie (CFH Marketing Manager), spend their Care Free time camping, reading, and raising their four children.

Care Free Homes Project ManagerDana Pickup, Jr., a graduate of Fairhaven High School, earned his bachelor’s degree from the University of Massachusetts at Dartmouth in 2004.  Upon graduation, Dana began working as a compliance specialist for Brown Brothers Harriman, one of the oldest, privately owned financial institutions in the country.  In 2006, he joined the family business and became the company’s project manager. He then returned to the University of Massachusetts at Dartmouth and graduated with his master’s degree in business administration.  As the Project Manager, he ensures projects are completed on time and that customers remain informed throughout the entire construction process. Dana volunteers much of his time to coaching his sons’ little league teams. He resides in Fairhaven, Massachusetts with his wife, Stephanie.

Care Free Homes Service ManagerBob Pickup spent most of his high school summers doing carpentry and small home improvement projects.  In the early 1980’s, he joined his older brother’s business and became the foreman of a roofing crew. By 1997, he was a highly skilled craftsman and became a project manager.   He excels in multiple areas of carpentry and is a certified installer of the Vinyl Siding Institute.  In addition to being an avid coin collector, Bob likes spending time with his wife, Colleen, their four children, and his grandsons.


Care Free Homes Office ManagerAndrea Caruso has been the mainstay of the Care Free Homes, Inc. office for the past 20 years. She attended Southeastern Massachusetts University (now the University of Massachusetts at Dartmouth) where she studied accounting.  With years of experience in corporate management and human resources, her knowledge of customers and company services are unbeatable.  Andrea’s superb skills as the office manager are essential to the day to day functions of Care Free Homes.  As an animal advocate, she has dedicated her life to rescuing unwanted or stray pets – making her house a Care Free home for dozens of unwanted and abandoned animals.

Care Free Homes MarketingStephanie Pickup studied writing and communications at the University of Massachusetts at Dartmouth. She is the marketing manager here at Care Free Homes and loves combining her passion for helping others with her love for home improvement. Stephanie is also the co-founder/author of Our Heroes’ Tree, a national initiative and e-book which honors the service and sacrifice of our nation’s military and their families.  Together with her husband, Nathan Pickup, she stays busy with four children, pet chickens, and their black lab, Bear. This Care Free mama enjoys reading, running, gardening, and volunteering in the community. 

Lisa Machado studied media and communications at Bridgewater State University. She is excited to start her career at Care Free Homes as our marketing assistant. Always with a smile on her face Lisa is passionate and puts herself into everything she does. Proud of her Azorean heritage she has spent some time volunteering with the Azorean Maritime Heritage Society, and speaks fluent Portuguese. In her spare time she loves spending time with close friends and family, binge watching her favorite shows on Netflix, and falling into the world of comics.


Just a few of the cities and towns we serve: AcushnetBarnstableBourne, Bridgewater, CentervilleCotuitCranston, DartmouthDennisFairhaven, Falmouth, Harwich,  Hyannis, Marion, Marstons MillsMattapoisett, Plymouth, Sandwich, SomersetYarmouthFall RiverNew Bedford, Newport, Onset, Providence, Portsmouth, TauntonWareham, Westport and Warwick as well as other towns on Cape Cod, Eastern Massachusetts and Rhode Island.