Family Owned ~ 508-997-1111 ~ Serving Southeastern MA & RI

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, Care Free Homes provides top-quality workmanship, reliable customer service, and outstanding product warranties. Care Free Homes is fully licensed and insured in both Massachusetts and Rhode Island and is an award-winning company with an extensive list of industry credentials. Care Free Homes customers are served by the Pickup Family and their own team of qualified craftsmen.

Stephanie Pickup

Stephanie Pickup

Marketing Manager

Stephanie studied writing and communications at the University of Massachusetts at Dartmouth. She likes to combine her passion for helping others with her love of home improvement. Stephanie is also the co-founder of Our Heroes’ Tree, a national initiative that honors our nation’s military families. This Care Free mama enjoys family time, reading, running, gardening, and volunteering in the community. 

Nathan Pickup, Sr.

Nathan Pickup, Sr.

Co-Owner, Vice President

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.

Dana Pickup, Jr.

Dana Pickup, Jr.

Co-Owner, Project Manager

Dana Jr. earned a bachelor’s degree in finance from the University of Massachusetts at Dartmouth. Upon graduation, Dana began working as a compliance specialist for Brown Brothers Harriman, one of the nation’s oldest, privately owned financial institutions. He has a master’s degree in business administration from UMASS Dartmouth. Dana is most Care Free while coaching, camping, painting with Bob Ross, and spending time with his wife and family.

Dana Pickup, Sr.

Dana Pickup, Sr.

Co-Owner, President

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. 

Andrea Caruso

Andrea Caruso

Office Manager

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 is most Care Free while rescuing animals, hiking with her yellow Labrador retriever, and relaxing at the beach.

Bob Pickup

Bob Pickup

Service Manager

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.

Tony Martin

Tony Martin

Crew Foreman

Tony is a Care Free classic – he’s been with us for over 30 years! He graduated from New Bedford Vocational School and immediately began his career in the trades. This talented carpenter is most Care Free while boating and relaxing by the ocean with his favorite cocktail. 

Neil Sullivan

Neil Sullivan

Crew Foreman

Neil graduated from Greater New Bedford Regional Vocational Technical High School and has been swinging a hammer ever since! He specializes in carpentry and has been with us for over 15 years. Neil is most Care Free while paddling a canoe and enjoying a day of freshwater fishing with his wife.

Jeff Prevost

Jeff Prevost

Crew Foreman

Jeff is a graduate of the Greater New Bedford Regional Vocational High School and has been with us for 8 years. Customers love his slightly shy demeanor and excellent craftsmanship. Jeff is most Care Free while freshwater fishing and spending time outdoors.  

Lisa Machado

Lisa Machado

Marketing Assistant

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.

Just a few of the cities and towns we serve: 

Acushnet,  Barnstable,  Bourne,  Bridgewater,  Centerville,  Cotuit,  Cranston,  Dartmouth,  Dennis,  Fairhaven,  Falmouth,  Harwich,  Hyannis,  Marion,  Marstons Mills,  Mattapoisett,  Plymouth,  Sandwich,  Somerset,  Yarmouth,  Fall River,   New Bedford,  Newport,  Onset,  Providence,  Portsmouth,  Taunton,  Wareham,  Westport and  Warwick as well as other towns on  Cape Cod, Eastern Massachusetts and Rhode Island.