There is a certain symmetry to Debra Taylor’s Martha’s Vineyard story. She first came to the Island in the early 1990s as a technologist who saw a challenge: A real estate market that was still using paper listing sheets and that needed the kind of multiple listing service she had already pioneered in Boston. She moved here for two years to build LINK Martha’s Vineyard, then headed back to Boston, job accomplished.
But the Island wasn’t quite finished with her.
A long-distance swimmer, Debra had made herself a promise while living here: Someday she would return and help raise money for something the Vineyard did not have — a year-round swimming pool. That promise eventually became an audacious idea: to swim from Chappaquiddick to Nantucket.
Everyone told her there was one person she needed to talk to before attempting it — legendary Edgartown harbormaster Charlie Blair, the man who knows these waters as well as anyone. On July 24, 2000, Debra made the crossing in eight hours, with Charlie helping to navigate the way. Twenty-five years later, they have raised two Island sons, Taylor and Tristan, and Debra has made Martha’s Vineyard both her home and the center of a business built around understanding one of the Island’s perennial obsessions: real estate.
Q: You weren’t a real estate broker when you started LINK. What was your background?
A: I’m software and data. I’m strictly tech. I was an economics major at Northeastern [University] and took coding classes — all on mainframes back then. I wasn’t a coder or software engineer, but I found a guy in Brookline who wrote my first software program in DOS. This was pre-Windows, pre-internet, pre-everything.
I started LINK in Boston in 1987, just as the condominium market was emerging. Because we were there at the beginning, we could build the database specifically around condos rather than trying to fit them into a system designed for single-family houses.
Q: What exactly does a multiple listing service do?
A: An agent needs to know: What’s for sale? What has sold? When are the open houses? When an agent subscribes to LINK, their buyers have access to the listings that are available for sale. It creates a transparent and complete marketplace. Today you would call LINK a SaaS company — Software as a Service. Agents subscribe to it just as you would subscribe to any other service. But when we started, remember, this was before Zillow, before the internet. It was a completely different world.
Q: So how did you make the leap from Boston to Martha’s Vineyard?
A: I got a phone call from a realtor on the Vineyard who said, essentially, “We hear you have a successful business in Boston. We could use something like this here. Come down and talk to us.” I had never been to Martha’s Vineyard. I didn’t even understand that you had to get on a ferry! I came down and pitched LINK to a group of about 20 people in the real estate community. A few weeks later they called and said, “We love your idea, but we’ve come up with another solution.” Their solution was that the agents would meet once a week in the basement of the Catholic church and exchange paper listing sheets.
The minute I heard that, I thought, “I need to move down there and get this up and running!”
Q: So you actually moved to Martha’s Vineyard because you saw a business opportunity?
A: Completely. I had never been here in the summer. I moved here year-round, single, and spent two years getting LINK established. I worked with Eleanor Wilson, who was trying to create something similar here at the same time. We ended up combining forces, and she was every bit as much a part of that startup as I was. It took about two years to get everyone on board and get LINK really humming. Then I thought, “Okay, I’m out of here.”
Q: What was the pull that brought you back to the Island?
A: Swimming was a lifeline for me — physical health, mental health, well-being — and there was no year-round pool here. Years later, I was walking at Cape Pogue with a friend on a windy, wintry day. I looked across the Muskeget Channel and asked, “What’s out there?” He said, “Nantucket.” I asked, “Has anyone ever swum there?” That planted the seed. Honestly, that swim picked me. I decided to make the swim a fundraiser for a year-round Island pool. We had raised funds that were used for an Island-wide survey, and the residents told us what they wanted: a gym, childcare and a pool.
Q: And is this where Charlie Blair enters the story?
A: Everyone I spoke to said, “Talk to Charlie Blair. He knows the water better than anyone.” I tried to reach him for four or five months. He never returned a phone call. Finally, I flew down to the Vineyard, walked into his office and before I was even through the door he looked me up and down and said, “I know who you are. You’re that swimmer from Boston.” And the next thing out of his mouth was, “The swim is doable, and I’ll do the navigating.”
Q: What is your most lasting memory of that eight-hour swim from East Beach on Chappaquiddick to Nantucket on July 24, 2000?
A: The most salient memory of my swim was the start. As I waded in up to my waist off East Beach, my fear dissipated as the Muskegat Channel was beckoning and the unknown about to unfold. I relive that moment the most. There is nothing like a good adventure.
Q: And when did you and Charlie become a couple?
A: We started dating that September, got engaged in November and were married in February 2001. Then we had our first child, and right after that our second. Both boys were raised here and went through the Island schools.
Q: Your son Taylor is a familiar face at Bettini at the Harbor View Hotel, and Tristan is a dock builder with Steve Ewing. That’s a strong Island presence! What is it like being married to Charlie Blair for 25 years?
A: My girlfriends say I’m married to an action figure. The Vineyard action figure. Actually, I’m married to an adventure — all day long.
Q: Is there a thread between the woman who saw the need for a multiple listing service and the woman who looked across Nantucket Sound and decided to swim it?
A: Swimming to Nantucket was a challenge. There had never been an MLS in Boston or on the Vineyard. That was a challenge. I love the challenge.
Q: LINK is now simply part of doing business here. What does your relationship with Island real estate agents look like today?
A: It’s seamless. You wouldn’t think twice about going online to make a dinner reservation. LINK is just part of an agent’s workflow. My forte is analytics. I give market updates and really look at what the market is doing underneath the headlines. But we are also about customer service. Eleanor is very hands-on with phone calls, and she has a cult following among the agents.
Q: In September the Island was rocked by news of the $43 million sale of two adjoining waterfront properties in Katama — one of the largest residential real estate transactions in Vineyard history. What does a sale like that tell you about where this market is headed?
A: I expect the trend of trophy locations and compounds to continue, mirroring other vacation home markets such as Nantucket, Aspen, Rhode Island and Miami. As shocking as it may be, it’s the norm for prime resort locations. What drives pricing into the stratosphere is the infrequency that these properties come to market.
Q: One discouraging part of the Vineyard real estate story is the assumption that first-time buyers have essentially been priced out. Is that what the data shows?
A: That’s misunderstood. There are first-time home buyers here, including year-round Brazilians who own companies, work hard and save. It’s the American dream — but the first-time-buyer price here can be $1.5 million and up. We’re also seeing generational wealth, with parents buying property for their children’s future. So, there is a first-time-buyer market but the bar is simply very high.
Q: The Vineyard has such distinct seasons. What do the seasons look like from a real estate perspective?
A: In terms of actual transactions, the majority of closings happen in the spring and fall. But there’s roughly a three-month lag. People are looking during the summer and those transactions close in the fall. Then people are looking through the fall and winter and those transactions close in the spring.
Q: You spend your professional life looking at the Vineyard through numbers and data. What doesn’t the data tell us about living here?
A: Living in a beautiful place is an essential ingredient, and the Vineyard is a beautiful place. Anyone who lives here gets to experience the magic. Real estate gets talked about as transactions — summer homes, seasons, prices. But those of us who live here year-round are here because we want to live surrounded by beauty all year. There’s a magnetic draw to the fresh air, the beautiful water and nature. That doesn’t show up in the data.
Q: And after the pace of a Vineyard summer, what does fall mean to you personally?
A: It’s my favorite time of year. The best swimming is September through November. For me, I’m all about the fall.
Sissy Biggers is the Q&A columnist for The Vine.