Tea Lane Associates began 50 years ago with force and chutzpah. With Eleanor D. Pearlson and Julia Green Sturges at the helm it was a potent combination.

The two women were as unalike as they were committed to each other. Their dynamic made for a powerful team, with cool-headed Julia being the only person who could reign in the fiery Eleanor.

The couple moved to the Vineyard in 1967 planning to open a real estate business. They purchased a large tract of land off Tea Lane in Chilmark with a vision to turn it into a subdivision. The plan, which they thought innocuous, turned out to be anything but.

“It was a 30-year struggle,” Eleanor Pearlson said in a 2006 interview with Marjory Potts. The old guard of Chilmark rose up in protest about their plan.

Eleanor’s niece, Leslie D. Pearlson, said in addition to the concept of a cohousing-type of development being unwelcome, the women themselves were a source of controversy.

Firm recently celebrated their 50-year milestone at Chilmark Tavern. — Jeanna Shepard

“They were also such outliers for being two women, two ladies,” she said. “They were given a lot of flak by the old timers in Chilmark who were like, who are these two ladies? They were just so unwelcome.”

But the Tea Lane women refused to back down. Out of the struggle, Waskosim’s Rock Reservation was established, and Tea Lane Associates slowly grew into a successful Island real estate business working in rentals and home ownership. The firm recently celebrated its 50th anniversary with a party at the Chilmark Tavern.

Tea Lane Associates is now run by two of Eleanor’s nieces, Abby Rabinovitz and Ms. Pearlson. Ms. Sturges died in 2003 at 98 and Eleanor Pearlson died at 89 in 2010. Tea Lane is a family business, by blood and by choice.

“It’s not just about family, it’s about understanding good people who really become family,” Ms. Pearlson said. “We’ve been so lucky with the team that we have, that they really are family, and that’s how we do feel. That’s the other part of family-owned, you can choose your family.”

Both cousins have early and dear memories of their Aunt Eleanor.

Growing up in New York, Ms. Rabinovitz remembers Aunt Eleanor coming to visit, bringing with her a book of old Union songs. They’d gather around the piano and sing together, belting out “I Once was a Union Maid.”

Leslie Pearlson points to her Aunt Eleanor, the founder of the firm. — Jeanna Shepard

“That’s my beloved aunt from when I was a little kid,” she said.

Ms. Pearlson remembers her aunt as larger than life. As a child she would visit Eleanor’s Chilmark cottage, first with family, then with friends.

“Eleanor was just always that crazy fabulous aunt you wanted to visit at any age . . . she was just so herself and so different,” she said.

Neither of the cousins were particularly drawn to real estate at first.

Ms. Rabinovitz was a flautist and composer, on the faculty of the New England Conservatory. Ms. Pearlson was a teacher. Ms. Rabinovitz came to Tea Lane first. She’d completed her first album, Flute Stories, and wanted to do a second.

“Gigs were slow, and Eleanor said, ‘come down, do some real estate and get some money for your second album,’” Ms. Rabinovitz recalled. So she did. It was about 20 years ago and the start of a completely different path.

Julia Sturges and Eleanor Pearlson.

“I did complete my second album, but I ended up staying,” she said.

Ms. Rabinovitz is now the majority owner of Tea Lane Associates. She co-owns the business with Ms. Pearlson who came to the firm a few years after her.

Ms. Pearlson had been teaching at a magnet school in New Jersey, but was ready for a new assignment. Eleanor, once again, provided the solution. She invited Ms. Pearlson to come to the Vineyard. The move to the Island was a wonderful one, Ms. Pearlson said, but it took a while to reconcile the vacations of her youth with a full time real estate gig.

“I didn’t realize my life would change so dramatically, that actually it would now become work . . . . I couldn’t just associate buying brie and crackers and sitting on the beach,” she said.

While working with Eleanor, Ms. Rabinovitz and Ms. Pearlson ushered Tea Lane Associates into the world of computers and digitized records, a change that Eleanor resisted. When the cousins began in the business, listings were kept on pink index cards and rentals were never locked. Eleanor would sometimes only show clients one house and could close a sale with a directive. “Eleanor really came from a time where she could just look at someone and say, ‘oh, you should just buy this, this is for you, you’re crazy if you don’t buy this,’ and that was enough,” said Ms. Pearlson.

And while now they have keys for every rental, show more than one house to clients and base rental decisions on more than just gut feeling, the transition into the digital age wasn’t seamless.

“There was a real tension for quite a while,” said Ms. Pearlson. “We definitely were ignoring her wishes to not go in the electronic direction, in the branding direction.”

Real estate on the Vineyard, especially the rental business, comes with its own set of struggles. From accidently showing the wrong house, to developing the skill to find a hidden key, to directing clients to hidden homes (sometimes with the help of streamers tied around trees) it’s not always a graceful endeavour.

Ms. Pearlson added that sometimes it seems like they live out of their cars.

“You should always have a change of clothes, a bottle of wine, a bottle opener, granola bars, a brush, a bathing suit and flip flops in your car, at all times,” she said.

A box of Chilmark Chocolates can also help soothe over ruffled feathers, be it a harried client or a speeding ticket.

Though there are now computers on the desks and locks on the rental doors, Eleanor’s way of doing things is still alive and well in the Tea Lane Associates offices.

“I watched and with Eleanor, she was drawn to so many different, wonderful people,” said Ms. Rabinovitz. “The people who bought from us, the people who rented from us, but also the people who worked with us in the day-to-day way. For her, it was really about people . . . we tried to keep that part of her.”