Chelsea’s Own Sandra Maddeford: A Trailblazer in Business, Art, and Life

Born and raised in Chelsea, Sandra Maddeford has built a life defined by talent, determination, and a deep love for her community. An astute saleswoman and gifted artist, Sandra enjoyed a highly successful career in real estate, founding Maddeford Real Estate in 1979—an agency that became a well-known and respected fixture in the city.

Now 90, Sandra continues to inspire those around her as a resident of Florence & Chafetz Home Assisted Living, part of Chelsea Jewish Lifecare, where she is beloved by staff and fellow residents alike.

A graduate of Chelsea High School, Sandra’s love of painting began early in life. Over the years, her artwork has been featured in numerous competitions and proudly displayed in her home. And her paintings continue to inspire—brightening not only her apartment but also the lobby of the assisted living. “Visitors always comment on how visually striking her paintings are,” says Kristen Donnelly, Executive Director of the Estates on Admiral’s Hill. Donnelly also noted what a wonderful addition Sandra has been to the Chelsea Jewish Lifecare family. “Beyond her artistic talent, Sandra is warm, funny and an absolute joy to be around.”

Sandra shared 33 years of marriage with her late husband, Charles “Chuck” Maddeford. They raised three children—Kenny, Larry, and Jenni—and Sandra is the proud grandmother of six: Christopher, Matthew, David, Caleb, Robert, and Hannah.

Her career in sales began with Avon, followed by years selling World Book Encyclopedia. It wasn’t long before Sandra found her true calling: real estate. After earning her salesperson license, she began her career at Cavaretta Real Estate in Revere. Driven by ambition and vision, Sandra received her broker’s license and opened Maddeford Real Estate.

One of Sandra’s greatest joys in business was working alongside her son Ken. “Sandra truly loved what she did,” he recalls. “My mom is genuine, kind, and trustworthy. People are naturally drawn to her. She has a way of making everyone feel welcome—and always has a smile and a laugh to share.

Sandra’s daughter, Jenni Crow, remembers her mother’s determination vividly. “One day she was showing a house in Gerrish Hall and her key didn’t work,” recalls Jenni. “That didn’t deter her in the least. Sandra just climbed through a boarded up window so she could show it to perspective buyers!”

Sandra’s community involvement has been as impressive as her professional career. She was a longtime member of the Chelsea Chamber of Commerce, served as President of the Everett Art Association, and was an active member of Temple Emmanuel in Chelsea, proudly embracing her Jewish heritage.

Ask her family what makes Sandra so special, and the answer is simple: her joy. “Sandra loves people and never complains,” says Jenni. Ken agrees, adding, “My mom’s laugh is unforgettable—she’s always loved to laugh, and it’s completely infectious.”

Sandra’s family is grateful she now calls Florence & Chafetz her home. “There are always so many activities to keep the residents engaged,” Jenni shares. “We know she’s well cared for and has much to look forward to every day. The staff truly feels like her extended family.”

Reflecting on her life, Sandra is most proud of her family and her accomplishments as a business owner. Yet through every chapter, one thing has remained constant—her love for Chelsea. “I’ve always held Chelsea in the highest regard,” she says. “It’s a place near and dear to my heart.”