Sign up for our Newsletter

Thomas McCloskey of Douglas Elliman Real Estate at one of his property listings. (Credit: Rachel Siford)

The North Fork has become a favorite spot for second-home buyers and the perfect escape for those needing a break from city life. To the surprise of many, it’s also the home of second careers for aspiring real estate agents who take lessons from their past to transform their lives.

We recently spoke with a trio of local real estate agents to talk about how they found their second career here on the North Fork. 

Thomas McCloskey

Douglas Elliman Real Estate

Tom McCloskey was a commodity trader on Wall Street from 1986 to 2012. After the market became computerized and he was left without a job, he decided to venture out to the North Fork.

When he made the transition to real estate, he was just a few months shy of turning 50.

“I was thinking about things I was interested in doing, and I had always been interested in real estate,” he said. “A lot of the same skills are utilized, as far as the market analysis.”

A big part of his job when representing a seller is getting the house priced correctly and positioning it in the market in comparison to other homes in the area. When he is representing buyers, he aims at getting them the best deal possible, analyzing the market and advising them on resale value, using many of the skills he acquired from his days on Wall Street.

He chose to join the team at Douglas Elliman because of their training program.

“The most difficult thing was just starting a real estate practice, for any walk of life,” he said. “It takes a while to build up a network of people and a following.”

His favorite time of year is September, because that’s when he gets back in touch with all his clients.

“What I enjoy about it is the fact that I get to work with people in a day and age when most people are looking into a computer screen 90 percent of the time,” Mr. McCloskey said. “I get to help them achieve their goals.”

When asked if he missed his city days, he quickly replied, “No.”

“It was a completely different type of career on Wall Street,” Mr. McCloskey said. “I like this better in the long run.”

He attributes his success as an agent to the strong sense of community and collaboration within his company and the area as a whole.

“What I like about the North Fork is that it’s a friendly culture out here,” Mr. McCloskey said. “When you leave Manhattan, with the hustle and bustle, and the pushing and the shoving, you decompress.”

Jill Dunbar

Douglas Elliman Real Estate

Jill Dunbar said she’s always found jobs where she listens to people and matches them to their dreams.

She owned the Three Lives & Company bookstore in the West Village from 1978 to 2001. Although bookselling and real estate may not seem to go together, she still uses all her skills from her former career.

“Clearly, showing a $20 book is not the same as showing a $500,000 house, but in terms of the process there is a skill there that I definitely use from my past,” she said.

Ms. Dunbar embarked on her real estate career after about 25 years running the bookstore. She was 55 at the time. She had also worked in an art gallery in the 1970s, making real estate her third career.

“It’s perfect because being an independent bookseller, you’re sort of on your own even though you have a shop that you go to every day, but you’re your own boss,” she said. “In this case, so is real estate.”

She had a house in Greenport as a weekend getaway, and when she sold the shop, she moved out east permanently.

“After taking a couple of years off to play some golf and do a lot of beach walking, I started in real estate,” she said.

A friend who was running the Century 21 office in Greenport encouraged her to go into the field and she got her license in 2004.

Although she’s still a voracious reader, she doesn’t miss her former careers. Running a retail shop in Manhattan was very intense, she added.

“All the skills you learn, especially the people skills, work in any area you end up in,” Ms. Dunbar said. “I like people. I like to listen. Everything I learned in my carriage trade still works in this business.”

Ms. Dunbar just turned 70, and said has no plans to retire.

“Fitting the hand in the glove and making the deal is the biggest and best thing about this job,” she said.

Rosa Ross

Daniel Gale Sotheby’s International Realty

Rosa Ross has been a professional cook all her life. She owned Scrimshaw restaurant in Greenport for 12 years, taught cooking, wrote cookbooks and has been doing private chef events. 

Ms. Ross, 81, decided just last year to change her path and join the team at Daniel Gale Sotheby’s International Realty.

She first got her license in 2008, but let it lapse while she was still busy with the restaurant. It wasn’t until early 2018 that she joined Daniel Gale and renewed her license to make it her new full-time passion.

“Everything has gone on the internet, so that was a big learning curve for me,” she said.

While she has been continuing her education through Daniel Gale, she still participates in the food industry with private chef jobs and pop-ups.

Inspired by the beautiful, pristine kitchens she shows potential buyers, she has been working at starting a blog called Kitchen Matches. It will incorporate helpful tips for home buyers, like how to stock a pantry and seasonal recipes.

“I’m trying to connect the two things,” Ms. Ross said. 

Scrimshaw closed in December 2016 and she took the test to renew her license in 2017.

Ms. Ross has been relieved since leaving the restaurant industry, because of the high stress of running a business and managing the food.

“In 12 years, I think I took two weekends off,” she said. “I was the first person in the restaurant and the last person to leave every night.”

She hopes she can grow her real estate business in the future.

“I find this new venture challenging, but in a very good way,” Ms. Ross said. “We are never too old to grow and learn.”