East Ender Jennifer Wilson has had somewhat of a ringside seat to the many changes in East Hampton over the decades, as a life-long resident, the daughter of shopkeepers and schoolteachers, and as a real estate salesperson with Saunders & Associates. Her parents, who met here in the 1960s, taught science and business in Sag Harbor, but also over the years sold real estate and, most notably, owned The Village Toy Shop, a local educational toy store “back in the days when East Hampton had mom-and-pop shops,” she says.
“When my parents had their store, in the summer months they were open from 10 to 10, because at 10 p.m. people were still walking around and shopping then. And that doesn’t happen anymore,” she says. “When I’d come home from college, I’d go into town when it was all mom-and-pop shops, and go to buy one thing in town and it would take two hours, because I knew everybody — the store owners, people walking around … it was nice.”
She praises Jerry Larsen, the village mayor, for developing creative ways to reactivate the village with sidewalk dining and other ways of bringing people back to the streets, but Wilson remains concerned about the cost of housing for local residents and the ability to uphold multigenerational home legacies. She and her husband raised two daughters here and are cognizant of the challenges they’ll face finding affordable homes to buy when they’re ready.
That’s but one reason Wilson, from the Springs district, is running for the East Hampton Democratic Committee to support changes for a more affordable future for residents.
“I’m doing this because I feel like we definitely need a change, and we need people to be so creative in making decisions that are going to help people like my kids and others with housing,” she says, voicing concern over the increasingly unapproachable local housing market.
“It’s really, very hard for that generation to stay here, and find affordable housing. Our towns out here have to get creative because it’s a huge problem, and it’s something that I really care about,” she says.
We asked about her East Hampton lifestyle, then and now.
Southforker: What are some of the significant changes you’ve seen in how people approach buying or selling?
Jennifer Wilson: I’d say 99% of all buyers are actively on Zillow, they’re starting their searches there before they’re even coming out to the market and they know the comps. They know everything — all the information is out there, so the real estate agent has to be very educated to keep up. I’ll reach out to brokers to find out where things are trading and for how much, just so I can be as knowledgeable as possible because the online estimates aren’t always accurate. Now every platform like homes.com or Zillow is incorporating AI into their searches. So I’m interested to see how that’s going to play out.
SF: What kinds of buying trends are you seeing the area?
JW: It’s a mix and I think it depends on where in East Hampton. What I have seen over the last 18 to 24 months and going into 2026 is that super high-end luxury market has really gone through the roof. Sales are off the charts and the prices are off the charts in areas where there’s a lot of generational wealth shift right now where a lot of money is being handed down in families. So I really see that at play. But there is the other side of the market where I have $2 million listings. I have a listing that’s close to $1 million and I have a team looking for opportunities at every level.
SF: Are there trends or specific lifestyle amenities people are looking for?
JW: In any size or price house, I think there’s a lot of attention to wellness. People want to come home and have a sanctuary … perhaps a meditation room or additional features, like a little spa or cold plunges or things like that, especially at the high end, those are really being incorporated. There’s also high desire for a seamless kind of indoor/outdoor lifestyle where really extending your living space into the outdoors.
SF: What do you like doing in your spare time?
JW: My husband and I have a Golden Retriever named Rocco and we love taking him for walks on bay beaches. We have a boat and that is a really nice way for us to just escape, so we are boating all summer as soon as it goes in the water and all fall.
SF: Any favorite local spots?
JW: We love Flaggy Hole Beach — you can see all the boats and sunsets from there. And we love food, so we eat out a lot. One of my favorite places right now, especially in the winter, is Tutto Café in East Hampton village right in the middle of the village, so you always see people you know.
