Second Acts: Jennifer DaSilva

From law practice to politics, to mediation, to Island real estate.


For most people, taking a work break means not working. But for Jennifer DaSilva, it means coming up with her next line of work. That’s how she went from corporate attorney to Martha’s Vineyard real estate agent. Of course, not that simply or directly.

Jennifer was born in Toronto to a South American family, raised in Queens and Long Island — at a young age she’d already been touched by three countries and two continents. She went to Duke, and on to Columbia Law School, clerked for a federal judge in Washington. D.C., married a finance exec, and practiced law for 17 years in New York and New Jersey, first in mergers and acquisitions, and then in her dream job as chief counsel to a $2 billion global division of Schering-Plough/Merck.

So far, no work breaks, and not a hint about real estate, other than vacations at the home she and her husband built next to her in-laws in Edgartown.

Meanwhile, another dream job came along, this time for her husband in the corporate world. The family relocated to Dover, which put them closer to the Vineyard for those vacation getaways. With two young daughters at home, an ailing mother, and a husband traveling internationally, this was surely the time for a work break. Instead, she got involved in the local school system — so involved that she ran for and became the first Black elected official in Dover, as chair of the school board/committee.

That was the end of any idea of taking a break, and the beginning of yet another career. Jennifer had met an ambitious young mother, also home with children and also with a traveling husband, and the two shared an interest in mediation. So they started a family and divorce mediation firm.

Many clients and mediations later, it was really time for a work break. What better place than the Vineyard?

“Every time I came to Martha’s Vineyard during the summer or the holidays, our builder, who had become a friend, and I would talk about local real estate,” she laughs. “These were the days when people didn’t have security cameras, so if a house was being built, we’d just walk through and talk about it …” The talk never ended; it became an obsession. One day her builder asked if she’d seen a development in Oak Bluffs called the Preserve — two- to four-acre lots on a beautiful 51-acre parcel. “We should do something here,” he said. Jennifer, who had zero experience in real estate (other than walking through half-built homes), said “Sure.” They formed a company — the builder, Jennifer, and her husband — bought two more lots, built the first houses from the ground up at the Preserve, put them on the market, and served on the board of the homeowners association: “I started to think, Maybe I should get my real estate license.”

Once again, the work break was over.

A year later, Jennifer joined Ocean Park Realty. “I loved it from day one. I improved my skills … I had nowhere to go but up.” With a daughter still in high school in Dover, Jennifer was only selling part-time, but that didn’t stop her from making a lot of deals. She often found herself across the table from the best agents on the Island, like Wendy Harman, owner of Point B Realty. One day Wendy asked to meet. “I went to her house for breakfast, and she said, ‘I’ll just get straight to the point. Of the 300-plus licensed agents on the Island. I’m No. 1, and you’re No. 2. What does it take for you to come over with me?’” Jennifer says, “I was shocked but thrilled that she would think so highly of me.” The catch was, she’d have to spend most of her time on the Island. “My younger daughter was now graduating high school, and the older one was in college, so I said I’d do it.” That was February 2020. New career, new job. What could go wrong?

In March 2020, COVID hit, and the world shut down. Not just on the Vineyard, but everywhere. People stayed home; grocery stores, restaurants, movie theaters were empty; offices were ghost towns. Even the Island ferries weren’t full. Of course, no one bought or sold real estate. For days, weeks, even with summer coming.

Then everything changed again. In May 2020, people started escaping big cities for more isolated venues — suburbs, rural communities, or even better, an island.

“Everybody wanted a house on the Vineyard,” Jennifer recalls. “People from Boston, Manhattan, Washington, D.C., everywhere.” But selling was different. “We either sold virtually, or I went with masks and gloves.” Sellers would turn lights on, open closet doors and drawers so no one had to touch anything. “Some buyers I never met without a mask until last summer in 2022.” Instead of dying, real estate boomed. Jennifer commuted from Dover during the off-season, spent summers on the Island, and her husband joined the ranks of the new hybrid workers with a home office.

Even as COVID receded, the real estate boom never let up. This June, they sold their house in Dover, and now call the Vineyard home.

It’s been an unexpected, circuitous journey from law practice to politics, to mediation, to Island real estate. Is there something about the Vineyard that makes it OK — secure and safe — to take that kind of leap?

“Yes,100 percent,” Jennifer says. “Most people here, especially in real estate, it’s their second, third, or fourth career. I work with someone who used to be a chef.” In contrast, “in my former life, most people like me went straight from college to law school, to work for a judge or the big law firm, much more of a path.” Her life here is off the path, literally. “Like yesterday, I got my lunch and sat at the beach. It’s just such a calming place to live and to work.” She laughs at herself, “I’m the only person, when I pull up with the other Realtors to an open house, who clicks my door and locks it.” That’s just who Jennifer is. She’s driven, and always working. She says her husband can shut it off and play golf for five hours, but not Jennifer. Not yet, anyway. Maybe never. She does make time for tennis matches, and serves on the boards of the Cottagers Inc. and the Boys and Girls Club.

For some people, a second act means searching until they find what fulfills them. For others, it’s all about the search itself, the energy, the pursuit, the next thing. That’s Jennifer. And it seems she’s found the perfect place to do it.



  1. Cheers to you Jennifer…your journey has been amazing to say the least! (and is inspirational for sure😉)
    The MV community is blessed to have you leading in a field that suits you so well! A “win-win!”

  2. What a wonderful story of ambition, reinvention , innovation and entrepreneurial zeal. Congrats and best wishes for continued success

  3. It’s great to see you pivot so beautifully, especially in areas that you have such passion for doing. Love the role modeling you provide to other women as well!

  4. When somebody asks me about buying real estate on the Vineyard I just give them Jennifer’s name and number. And they always thank me later.

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