Hamptons Confidential: Gioia DiPaolo


Welcome to our new feature in which we interview local personalities: agents, architects, interior designers, builders, anyone who plays a part in the world of Hamptons real estate. Want to get in on the fun? Drop us a line!

Gioia DiPaolo has been a top agent in the Hamptons for more than 20 years–these days she works out of Douglas Elliman’s Sag Harbor office. Before that, though, Gioia was a fashion designer and manufacturer, supplying stores such as Neiman Marcus, Saks Fifth Avenue, Bloomingdales, and Macy’s. So how did a girl from South Jersey wind up selling Hamptons real estate?

So you’re originally from New Jersey?

I spent my formative years on a small farm in South Jersey surrounded by extended family and nature. Very happy times, very rich sense of community.

Where do you live now?

I live in Greenport. I love starting and ending the day on the water as I commute by ferry to Sag Harbor.

How did you end up in the Hamptons?

I was living in Manhattan, owned a weekend house here, and over time just eased in to full time living.

What did you do before you were an agent?

I designed and manufactured accessories and cocktail dresses in Manhattan under my own label.

Gioia’s listing at Vitali Cilli Ave, Sag Harbor, asking $10.5 million

What do you like to do in your spare time?

I like to have meaningful discourse with original thinkers preferably over amazing food and wine. I also like a lot of alone time.

If you weren’t an agent, what would be your dream job?

I’d be a Jungian Psychoanalyst helping people get in touch with their true selves.

What are some of the best things about being an agent in the Hamptons?

I meet a lot of interesting people. I’ve made lifelong friendships through my work in real estate here.

What are some of the drawbacks of being an agent? 

Most professions have office hours. Not so in real estate. People expect to be able to reach you 24/7 anytime of day or night.

For the most part I don’t really mind that as I am totally connected to the business of real estate.

What’s the best advice you ever got, personally or professionally?

Never step out of the house not looking your best.

What do you think of the Hamptons real estate market right now?

With high inventory levels, low interest rates and softening prices, there is a lot of interest from buyers. I expect to see great payoffs in in the third and fourth quarters.