The president and CEO of Carl M. Freeman Cos. has not only led several property development initiatives, but she’s also helped to cultivate a growing arts and culture outlet in Freeman Stage productions.

It’s not often that you see a Delawarean in the glossy pages of a fashion magazine. But flip through Elle’s March issue and you’ll spot a fetching photo of Michelle DiFebo Freeman. Wearing a stylish blouse with white cuffs and collar over low-cut lace, she looks as chic as any model. Yet it wasn’t her looks that landed her in the high-profile magazine. She’s among the 10 women that Elle dubs an “influencer” in the Washington, D.C., area.
Freeman, who splits her time between Montgomery County, Md., and North Bethany, is president and CEO of Carl M. Freeman Cos., which develops and manages commercial and residential properties. Local projects include Bayside, the Village of Bear Trap Dunes and Sea Colony. She also chairs the Carl M. Freeman Foundation and the Joshua M. Freeman Foundation, a tribute to her husband, who died in a helicopter crash in 2006.
Freeman and sister Lisa DiFebo Osias grew up in Wilmington, but they spent summers at the family beach house in Bethany. They both liked the beach so much, they moved there. Osias became a restaurateur. Freeman, who’d worked for years at Crabber’s Cove and the Rusty Rudder, helped. But her heart was in another profession.
“I’ve always loved houses and been in love with the land,” she says. “My sister’s passion is food and mine is real estate.” After getting her real estate license, she started working at Sea Colony, where she caught the eye of the “boss’s son,” Josh Freeman. “It was a big scandal,” says Freeman, who was a single mother.
Her husband became the company president in 1995. (Carl Freeman died in a car accident in 1998.) Upon Josh’s death at just 42, Freeman, who had three children, took over his duties. Within a year, she launched the Joshua M. Freeman Foundation and a series of cultural programs on a small stage, seeking to cultivate the “art desert” that existed in Sussex County.
More than 65 percent of Freeman Stage performances are free to the public, and students 18 and under receive free admission, except for national acts. While headliners—Lyle Lovett, Sheryl Crow, Pat Benatar—bring recognition to the venue, they also fund outreach programs. The foundation, for instance, often holds events in Georgetown in the off-season.
Freeman also has a business to run. Bayside, which broke ground in 2000, is about halfway to its goal of 1,500 homes. She’s watched the real estate market plummet, but each year since 2008, Bayside sales have improved. “Our fingers are crossed,” she says.
Since 2000, more full-time residents have moved into the community. “There’s so much more to do,” she says of Bethany and Fenwick. “It used to be like a ghost town.” Health care and education have improved. And, thanks to Freeman, cultural opportunities have increased. If she has her way, they will continue to grow. “It’s been an incredible journey,” she says.

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