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 20 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, unlike many companies, by our own team of qualified craftsmen.

The Care Free Homes, Inc. Family

dana pickup fairhaven maDana Pickup, Sr. was 23-years-old when he co-founded a small, home improvement from the living room of his home.  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 home improvement companies serving Cape Cod, Southeastern Massachusetts, and Rhode Island.  Dana’s three sons, Nathan, Russell, and Dana John, are partners in the company and maintain the family commitment to quality, craftsmanship and service.  Dana still serves as president of Care Free Homes, Inc.  In his free time, Dana can be found cheering for his seven grandchildren at various sporting events or enjoying an afternoon motorcycle ride with his wife of 39 years, Joan.


Nathan Pickup, Sr. graduated from Fairhaven High School before earning his bachelor’s degree from the United States Military Academy nathan pickup fairhaven maat 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. Nathan serves as Vice-President of Construction Services and Care Free Homes, Inc.  He donates much of his time to coaching CYO basketball for his three daughters and T-ball for his son.  He and his wife, Stephanie, have been married for 15 years and reside in Fairhaven, Massachusetts.


Russell Pickup is celebrating his 18th year at Care Free Homes.  Fresh out of high school, he began his career russell pickup fairhaven maas a carpenter on a framing crew building custom homes, decks, and porches.  After gaining much knowledge as a carpenter, he became a skilled craftsman and led his own framing crew.  He continued to progress and began using his hands-on experience to provide customers with expert advice for their home improvement projects. Russell is the Care Free Homes sales manager and has a devoted client list that continues to grow with every appointment.  Russell is most “care free” when cruising in his Jeep with Bandit, his beloved Australian Cattle dog.


Dana Pickup, Jr., a graduate of Fairhaven High School, earned his bachelor’s degree from the University of Massachusetts at Dartmouth dana pickup jr fairhaven main 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 Projects 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’ soccer and T-ball teams. He resides in Fairhaven, Massachusetts with his wife, Stephanie, and their three children.


Bob Pickup fairhaven maBob 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, and their four children.  The couple resides in Fairhaven, Massachusetts.


Andrea Caruso has been the mainstay of the Care Free Homes, Inc. office for the past 17 years. She attended Andrea Caruso fairhaven maSoutheastern 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 the Care Free Homes Company.  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.


stephanie pickup fairhaven maStephanie Pickup studied writing and communications at the University of Massachusetts at Dartmouth.  She is a published author and journalist whose work has been featured in local and national publications. 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.  As the Care Free Homes marketing manager, she works beside her husband, Nathan, and is helping map the future for the Care Free Homes Company. She volunteers as a 5K road race coach for the East Fairhaven Elementary School’s Sole Sister Program where she trains with her daughters and promotes physical and emotional wellness for young girls.


Erin Conner fairhaven maErin Conner is the newest member of the Care Free Homes, Inc. team.  Over a period of 5 years, she earned a Bachelor of Science in Marketing from the University of Massachusetts at Dartmouth (Class of 2010) while simultaneously working as customer service and marketing coordinator for a laboratory supply company.  As a student, she volunteered in the Lower Ninth Ward of New Orleans to rebuild homes destroyed by Hurricane Katrina.  She is most care free while cooking and spending time with her husband, Kyle, and their dog, Chloe.




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.