Real Realty

Gioia DiPaolo Knows That Fortune Favors The Bull

DiPaolo showcasing her exclusive at 330 Main Street in Sag Harbor Village. Independent/Ty Wenzel

Andy Warhol once said, “They always say time changes things, but you actually have to change them yourself.” Gioia DiPaolo understands the twists and turns of Hamptons luxury real estate so much so that she changed agencies a few times to make sure she was not missing the best path. It was also during these pivots that DiPaolo understood the best way forward had always been at Douglas Elliman.

We were one of those fans of yours that were captivated when you posted on Instagram the Elliman logo with the caption “CHANGE” after leaving for Sotheby’s in 2017. You’ve certainly tested the waters elsewhere, such as joining Corcoran in Sag Harbor as well. Yet you gravitate back to Elliman.

I have so many long-term relationships with Elliman people — some of us worked together at Corcoran, so it’s like a family. Elliman seems to support the entrepreneurial spirit; they appreciate innovation in their agents. Howard Lorber is a great leader.

You worked with Dottie Herman ages ago, back when Elliman first opened in Sag Harbor. What was it like to work with the legend?

Dottie is brilliant and street smart, funny, tireless; fearless, unconventional. I learned so much from her early in my real estate career.

You’ve brokered some amazing deals, such as the Castello di Borghese Vineyard in Cutchogue and the Saks Fifth Avenue building in Southampton. What do you offer these titans that others may not?

Thinking outside the box and always believing anything is possible.

Were you ever a regional director of some kind or always a broker?

I was the manager of the Sag Harbor Office for five years, which required me to become a broker. I was asked to take a regional position at one time but turned it down. I love listing and selling real estate. Managing was rewarding in its own way though — it brought out a nurturing side I didn’t know I had. I really enjoyed mentoring and assisting agents develop their careers.

Are you local?

I am not a local, but I’ve never felt like an outsider here. I bought a weekend home here after I sold my house in Bucks County. I was living in Manhattan and working in the fashion industry at the time.

Why are you a signature specialist in Sag Harbor real estate in particular?

I feel at home in Sag Harbor. I’ve made best friends for life here. I love the historic architecture, the way you get to know everyone in a small town. Walking down Main Street to the water is very special.

What is the biggest mistake sellers make in your opinion?

Not pricing a house properly is probably the biggest mistake sellers make. Find an agent you trust and have them show you the comps and the competition.

Do you have any particular advice for buyers?

Don’t think you’re being smart by only seeing a house with the listing agent.

Is there something about the East End that inspires you?

I love the farmland and open spaces that still exist.

Are there any up-and-coming neighborhoods we should know about?

I’ve always loved the North Fork, the farms and vineyards. Greenport is amazing! It’s a hip maritime village still somewhat lost in time while offering an incredible restaurant scene. Real estate there is very affordable.

What do you do for fun when you’re not working?

I need a lot of alone time and a few great friends. I like to eat beautiful food and drink nice wine with interesting people who are smart and fun. I love spending time in Italy and I enjoy visiting family and friends in LA. Every year I go someplace I’ve never been before.

To reach DiPaolo or inquire about her properties, call 631.903.2937 or email