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Sag Harbor-based real estate agent Gioia DiPaolo’s career would be fascinating enough if her 11 years of selling real estate in the Hamptons was the only topic of conversation, but this renaissance woman who recently left the Corcoran Group to join Prudential Douglas Elliman, where she got her start in the business, had a storied career before she sold her first house.
A native of Philadelphia, Ms. DiPaolo initially enrolled at the University of Pennsylvania with a plan to study either art or law. When neither struck her fancy, she moved to Capitol Hill, where she quickly landed a job in a senator’s office. In the ensuing years, she’s been a real estate developer in Philadelphia with her former husband, run a fashion design company in Manhattan and become a devoted collector of art and photography.
Ms. DiPaolo discussed her career and the unique pleasures of her life in Sag Harbor over sandwiches and salads at The Dockside, overlooking the harbor that gives the village its name, one afternoon just before Christmas while she was in the midst of planning a trip to Paris over the holidays.
Q: Did you always work in real estate in Sag Harbor?
A: I’ve always been in the Sag Harbor office, but I always worked in other areas as well, even though my office was based here. From day one, very early in my career, I went over to the North Fork and sold several large vineyards. I sold Hargrave Vineyard, which was the first vineyard on the North Fork, to the Borgheses. It is now Castello di Borghese. I sold Gristina Vineyard, which was another early vineyard, and I sold a couple of other parcels that were put together to make those vineyards bigger. I like to go where the action is, if it’s exciting to me, and that was because I love the wine industry and I love wine. I’ve done business in Bridgehampton, as far as Amagansett, I had the exclusive listing on the old town hall building in Southampton where Saks Fifth Avenue is. I’m based here, but I’m really a Hamptons agent.
Q: How long have you been in the business?
A: This is going to be the 12th year. I started out with Prudential, so I have this big history with Prudential. I started when Dottie Herman first opened a little office in Sag Harbor. I’d been in the fashion business in Manhattan. I worked for her for eight months and went across the street to Cook Pony Farm, which was taken over by Corcoran and October 1 I went back to Prudential. It’s like coming home. I really respect Dottie Herman. She’s a fantastic human being and a fantastic businesswoman. It’s a huge company and it has global reach, but she’s a human being and she’s there. She’s personally invested in this company and she’s available. It’s fantastic to be part of a company where the principals are involved. I didn’t leave Corcoran because I was unhappy there. I loved Corcoran, but I have to say, for all of the three buyouts, none of the agents were happy to be bought out. They saw it as a hostile takeover when it wasn’t. None of the three firms were happy about that and I was one who was happy about it. I loved having the Manhattan connection. Most of our buyers are from Manhattan. I loved the sophistication in their graphics. I was the top producer in their office every year. It’s a great company.
Q: Was the switch really about working with Dottie again?
A: I was with her organization early on, and I saw her vision. Over the years, I saw that vision come to fruition. When she bought Douglas Elliman in the city, I thought that was the time. I was really close to going back again, but I didn’t make a move then. She loves this business and she started out as an agent. That’s really important.
Q: How did you get involved with the wineries?
A: I had just started in real estate and I loved the wine industry. I thought it was something that had a huge amount of potential. Before I got into real estate, the other industry that really appealed to me here was the wine industry. When I first started, I came across Hargrave Vineyard as a listing. I said, wow, I’m getting in my car and going from there. I got the listing in my office and brought in the buyer. It was very serendipitous. It was friends of mine from Philadelphia who weren’t even thinking about buying a vineyard or leaving Philadelphia. He grew up outside of Florence and I knew he would relate to it. I thought I would just introduce him to it. We talked for almost a year, but they fell in love [with] it. I find most real estate sales are very emotional like that. You walk in and I can usually tell when you walk in. It’s that feeling that takes your breath away and you know this is your house.
Q: What was the first property you sold?
A: It’s very poignant right now in this market, because the first property I sold was in foreclosure. At that time there were very few. It was one house back from the bay. I sold it in the first week or two after I joined the company. I showed them one house. They bought the house, and I thought, “This is easy.” This past 11 years has been like that. But things have definitely leveled off. Prices have come down. But if you bought something in 1999, you’ve still made money. Right now is the best climate to buy real estate in 10 years. There’s a huge amount of inventory—good inventory. Interest rates are low. If you’ve got good credit, there are loans being given.
Q: I guess finding buyers is the hard thing.
A: A lot of people are really wanting to be here and waiting. I don’t think everybody’s lost all their money yet.
Q: Have things started to pick up since the October uncertainty?
A: I would say, in the past month or so, the sellers who really want to sell and who need to sell have lowered prices, and the lowered prices have stimulated activity. I’ve never been able to establish any rhyme or reason to it. It’s not like a primary home market. It’s very unpredictable.
Q: So, you hadn’t done anything in real estate before you came here?
A: I do have a background in real estate. I’m from Philadelphia. When I was in Philadelphia, my husband was a real estate developer. He bought commercial real estate and I was involved in business with him. I think that was why I was very comfortable doing commercial transactions. I had relationships with tenants and leases and all of that. We were involved in the rehabilitation of a whole neighborhood.
Q: How did the fashion industry come into play?
A: That was my love. When I got divorced, I wanted to do something that was just my own. I had read an autobiography of Ruth Gordon, the actress. She said, “Do something you love to do and find a way to make money.” I didn’t have any training. I’d graduated from the University of Pennsylvania, pre-law. I though I was going to be an attorney. I just figured out how to do it. I created one collection and I showed it to the top stores in New York. I went into Saks Fifth Avenue, stores of that caliber. Then I had to learn how to run a business. It was a fun career, since it was my own little company. I designed, manufactured, did all my own public relations, did all the negotiations with the stores. Having that business and being accustomed to the work ethic, everything comes back to you. That work ethic carried over into my work as a real estate agent. I never really worked for anyone. I worked for myself. Real estate agents are contractors. Every agent really is running their own company. That really is the best training, taking full responsibility for your business.
Q: I’d heard that you worked for a senator?
A: That was my first job. I lived in Washington, D.C. I worked for Harrison Williams, who was a Democratic senator from New Jersey. He ended his career not on a great note. Even working there, I became very accustomed to working with power brokers and celebrities. Every single thing I’ve ever done has led me to real estate in the Hamptons. I don’t know if I could do real estate anywhere else.
Q: What did you do in Harrison Williams’ office?
A: At one point I was his appointments director. He had this show that he did on radio, and I’d transcribe that fireside chat. At different times I’d be the receptionist. Nobody ever saw the senator. Nobody ever talked to the senator. They talked to me.
Q: Were you still thinking of being a lawyer at that point?
A: No. When I was at Penn, I worked at a law firm to see if I really liked it and I decided it was probably the last thing I wanted to do.
I recently became a certified ecobroker. I think that is going to impact the world in general, but I think it’s going to impact this area, too. I think people that want to have huge houses want also to have a house that is healthy and I think that will be part of the green movement, as well as being more affordable to run. I think people are really starting to think about that.
Q: Are there many ecobrokers out here?
A: Prudential put together a course. They got an ecobroker to come and teach our agents in one huge conference room. There were 30 Prudential agents who all became ecobrokers at once. I have two listings, one they’ve just dug the foundation, but it’s going to be a LEED certified house. The other is going to be an EnergyStar house. I didn’t know what that was. I figured I’d better learn. Green is a term that’s thrown around lightly and it sometimes doesn’t mean anything. I’m very conscious about that. I think more and more people want that. The LEED house is in North Haven. The builder, Charles Rich development, his office is in Southampton, is starting a website that will show the development and the materials that are being used for people that are interested, which is a lot of people these days. There are a lot of ways to bring houses up to speed and people are going to be doing more of that. There’s solar, insulation, radiant heat.
Q: For a long time the Sag Harbor ARB had a big problem with solar. I don’t know if that’s still an issue.
A: Have you been following the solar “farm” in Bridgehampton? Those kinds of things are big issues here.
Q: You were involved with the Southampton Historical Museum?
A: It seems like everything I get involved in revolves around houses. I was a trustee for seven years. I did a lot of fund-raising for the renovation of the Halsey House on South Main Street. The cedar shingles were more like swiss cheese. It was a big job. The other organization I’m involved with is called Miracle House. It provides housing in Manhattan for people who have life threatening diseases. Miracle House provides housing for their family members and caregivers. They come to New York and they’re so lost. It’s so expensive. It always comes back to real estate.
Q: That’s just such a basic thing. Most everything revolves around people’s relationships to buildings. Do you deal with historical properties?
A: Oh, yeah. Sag Harbor, most of the village is in the historic district.
Q: There have been so many amazing renovations.
A: The thing about Sag Harbor is the people who come here seem to bring a lot of respect for village architecture. Very few people come here and just want to tear stuff down.
Q: I was just on the phone all morning with people who were upset that the Elaine Benson Gallery was torn down in Bridgehampton. I guess part of the problem there is they don’t have a historic district?
A: It’s not like Sag Harbor. We’ve got our Architectural Review Board and they’re not unreasonable, but they’re very thoughtful of maintaining that character. But I love the layers of architecture here. I don’t have a horrible aversion to the new layer. I mean the condos on West Water Street. It’s really going to be amazing construction and very upscale. It’s modern architecture, but it’s the new layer.
Q: I’d heard you were an artist?
A: I’m not an artist, but I love art and I collect art. I have paintings that I love. I like black and white photography. I have a lot of Pennsylvania Academy of Fine Arts artists from many different periods—from the 1800s to the 1960s. I love Jim Gingrich. He’s a local guy. I have four pieces of his. When I was at Cook Pony Farm we would show local artists and I would curate those shows. I’ve collected local artists. When I was at Penn, I also worked at the Philadelphia Art Museum. My major was American civilizations. With that major, I could have gone into law or art. I was torn between the art world and law. I worked part of the year for a law firm and part of the year for the museum. I decided I didn’t want either of those. In the museum world you’re in a small pond, but I love art.
Q: Do you have enough walls to put the paintings on?
A: I have a place in Del Ray Beach, Florida, so I have a lot of stuff there. I have this portrait painting of an ape. He looks so wise, so composed. At one time I had him hanging with a couple of family portraits. He has such an intelligence in his eyes. I have one portrait of a striped bass that Jim Gingrich caught in Montauk. He had the fish taken to Suki Zuki and made sushi out of it. But I got the portrait.
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