Care Free Homes Co., Inc.

Dana 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.

Dana, Sr. co-founded Care Free Homes with his brother-in-law, Wayne Edwards. Since 1978, their small roofing, siding, and window business has evolved into a full service home improvement and construction company. Dana now co-owns Care Free Homes with two of his sons, Nathan and Dana Jr.. This Care Free guy enjoys making memories with his wife and family, camping, and motorcycle rides. 

Nate graduated from the United States Military Academy at West Point. He 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’s Care Free hobbies include family camping, hiking, reading, and boating.

Andrea has been the mainstay of our office for over 20 years. She studied accounting at Southeastern Massachusetts University and has years of experience in management and human resources. Andi has a huge heart for animals and has provided a Care Free home to dozens of rescued pets. She is happiest while hiking with her yellow Labrador Retriever, Belle, and relaxing at the beach.

Bob is a great friend of the Pickup family and has been a lifelong resident of the SouthCoast. He holds a degree in Business Management and has decades of experience in residential and commercial real estate. This Care Free guy has a talent for sketching and painting and is most Care Free with family, relaxing at the beach, or playing a round of golf.

Lisa studied media and communications at Bridgewater State University. She is proud of her Azorean heritage and enjoys volunteering with the Azorean Maritime Heritage Society. Always with a smile on her face, Lisa is most Care Free with close friends and family, binge watching her favorite shows on Netflix, and falling into the world of comics.

Stephanie studied writing and communications at the University of Massachusetts at Dartmouth. She loves to combine her passion for helping others with her love for home improvement. Co-founder of Our Heroes’ Tree, a national initiative that honors military families, this Care Free mama enjoys family, workouts, reading, gardening, and volunteering in the community. 

Bob spent most of his high school summers doing carpentry and small home improvement projects.  In the early 1980’s, he began his career here at Care Free Homes. He excels in multiple areas of carpentry in addition to being a certified installer of the Vinyl Siding Institute. Bob is an avid coin collector and is most Care Free spending time with his wife and their family.