For years, Greenport has stood out among East End communities for its laissez-faire policies on short-term rentals, but that latitude may be coming to an end. At a sometimes-heated public hearing Thursday night, residents, property owners and village officials wrestled with a 33-page proposal to tighten restrictions on rentals in the village.

Mayor Kevin Stuessi reminded residents that every other East End town and village already imposes stricter rules — many requiring rentals of two weeks or 30 days.

“Greenport currently has the most liberal short-term rental code of the entire Eastern End,” Stuessi said. “We do need to make corrections to it.”

While every local municipality has struggled with the consequences of short-term rentals popularized by websites like Airbnb and VRBO, Greenport has shouldered an especially heavy burden, according to a report released last year by the Southold Town Planning Board. Data and maps provided in the survey illustrate Stuessi’s assertions.

In the spring of 2024, Greenport Village and Greenport West accounted for the highest number of short-term rentals in Southold Town, with 293 rentals — part of an increase of 34% over figures from the previous spring.

Greenport officials contend that unchecked growth of Airbnb-style stays is driving up rents, hollowing out neighborhoods and threatening the village’s year-round character. Yet last summer, when they proposed limiting all rentals to 30-day minimums, officials were met with intense pushback in public meetings.

Riverhead currently requires a 30-day minimum stay for rentals and Southold, which requires a 14-day minimum stay, recently renewed a moratorium on new hotel construction.

What the proposed legislation would mean

The proposed legislation would overhaul Chapter 103 of the village code and require every rental property to carry a valid permit by January 2026, whether long-term or short-term. Rentals under 30 days would be limited to single-family homes and certain two-family properties. Apartments in larger multifamily buildings, accessory cottages and employee housing would not qualify.

Even in eligible properties, village officials want strict oversight. Short-term rental permits would fall into three categories: hosted, owner-occupied and resident-occupied. In each case, an owner or resident must be living on-site during guest stays. That provision is designed to block absentee ownership and investor-driven conversions of housing into commercial lodging.

The proposal would require new paperwork and compliance for property owners. Applications would require floor plans, insurance coverage, waste-management plans and safety certifications. Rentals would be capped at two people per bedroom, no more than eight total occupants. Parking, noise and trash rules would be tightened, and all online listings would have to display a village-issued registration number.

Violators could face fines ranging from $500 to $5,000, loss of permits and a three-year ban on renting. The village proposed code update also reserves the right to seek court-issued search warrants for suspected illegal rentals. In framing the law, village officials said the goal is not to eliminate short-term rentals but to protect Greenport’s identity as a “living, working community” while still welcoming visitors.

Code enforcement

Resident Karen Rivara spoke in favor of the new code but urged enforcement above all else. She described a revolving-door atmosphere on her block of Carpenter St., where she said cars jam the street and units are turned over in 48 hours.

The village currently has no full-time code inspector and has struggled in recent years to attract new hires because it can’t afford to pay competitive civil service salaries.

Some questioned whether new rules would help at all without increased enforcement.

“You’re going to have to have a whole [code enforcement] division just for short-term rentals,” warned resident John Winkler, who accused the village of failing to enforce existing laws. Winkler, who has rented rooms in the village for more than a decade, said changing the rules now without grandfathering in existing operators would invite lawsuits.

“I lost bookings because I was doing the right thing,” he said. “You didn’t enforce the old code, and now you’re punishing people who followed it.”

Winkler said law-abiding, owner-occupied renters like himself would be unfairly punished under code proposed to weed out illegal rentals.

“I followed all the requirements that you put forward for 10 years … now you change it,” he said. “I think that anybody who’s been doing it should be grandfathered. That’s what usually happens when you have a business.”

For John Kramer, who owns what he said is Greenport’s only legal three-family short-term rental, the new rules would be devastating.

“The wedding industry is going to feel it. The yacht clubs are going to feel it. The florists, the caterers, the restaurants — they’re all going to hurt,” Kramer said, estimating his guests alone spent more than $40,000 locally this year.

But Planning Board chair Patricia Hammes countered that unchecked short-term rentals were ruining neighborhoods. “I didn’t buy my house to live next to a hotel,” she said. “It’s destroying the fabric of our community.”

Hammes echoed Stuessi’s assertion that even under the proposed code, Greenport would still allow more flexibility than neighboring East End communities.

Dinny Gordon, head of the village’s new Housing Committee, tried to widen the lens. Citing census and rental-tracking data, Gordon said more than 90 percent of Greenport’s short-term listings are whole houses, often investor-owned. Nearly a third of the village’s 1,442 housing units were vacant in 2023, with 59 percent reserved for seasonal or recreational use and “therefore unavailable for permanent residents.”

“Twenty eight [rental] parcels are owned by one company,” she said. Almost half of Greenport households just below the median income, she added, now pay more than 30 percent of their income on housing.

Seeking middle ground

Trustee Julia Robins said the board needs to strike a careful balance.

“My neighbors are involved in this, and it’s not a problem when people rent part of their house,” she said. But she agreed with calls to create an appeals process for the new parking requirements, which several residents argued would unfairly burden older homes with no off-street capacity.

Deputy Mayor Patrick Brennan acknowledged the divide.

“I don’t necessarily agree with everything I’ve heard, but these comments are critical to us trying to get this right,” he said.

For now, the board extended the hearing another week. Stuessi said the aim was not to kill Greenport’s visitor economy but to rein in abuses and create a code that can stand up to legal scrutiny. He defended the 33 pages of proposed revisions.

“We are proposing something very liberal,” he said. “But it requires a lot of language.”

The public hearing on Greenport’s proposed rental code updates will continue on Thursday at the board’s 6 p.m. regular session.