If you've been eyeing a place in Greenport purely as a weekend rental play, you've probably heard the village just became the most flexible spot on the East End for exactly that. No minimum stay. Rent it Friday to Sunday if that's the market. So why can't you simply buy a condo there, list it on a booking platform, and never set foot in it yourself?
The answer sits inside the code the Village Board rewrote this past winter, and it's the kind of detail that never survives the trip from a portal listing to a closing table. Greenport did drop the stay-length rule it used to share with the rest of Southold Town. What it added in the same breath was an occupancy requirement that rules out the exact buyer who reads "no minimum stay" and hears "easy income property."
The Vote That Rewrote Chapter 103
On Dec. 4, 2025, the Greenport Village Board voted 4-1 to overhaul Chapter 103 of the village code, the section governing rental properties. The new law took effect Jan. 1, 2026. Owners had 60 days from that date to apply for a permit, with permits required to be in effect within 120 days of the new year.
Mayor Kevin Stuessi cast the lone dissenting vote. He said he would have preferred sticking with a two-week minimum to match Southold's rule, and described the law that passed as "very different than anything else on the entire East End." Trustee Julia Robins took the opposite view, calling the law flexible enough to adjust if it didn't work: "It's flexible, and if we need to change it in a year, we can change it."
The urgency behind the rewrite had a number attached to it. A Southold Town Planning Board survey found that in spring 2024, Greenport Village and the surrounding Greenport West area accounted for 293 short-term rentals, the highest concentration in the entire town, and a 34 percent jump from the year before. That's the backdrop against which the mayor had previously described Greenport's old rule as "the most liberal short-term rental code of the entire Eastern End."
The board also set the new fee schedule: $750 for an annual short-term rental permit and $250 for a two-year long-term rental permit. And in the same meeting, trustees voted to request state legislation authorizing the village to impose its own occupancy tax on transient lodging, capped at 4 percent of the per diem rate, a request that still needs Albany's sign-off before it becomes collectible.
Three Ways In, All of Them Require You to Actually Live There
Here's where the trade-off shows up. The new code creates three permit categories for short-term rentals, and every one of them anchors the rental to someone actually residing at the property.
A Hosted Short-Term Rental requires at least one bedroom in the unit to be reserved for the owner or a resident tenant, on site, during the guest's stay. An Owner-Occupied Short-Term Rental allows the whole unit to be rented, but only if the owner occupies the property for part of the year. A Resident Short-Term Rental applies to two-unit properties where one unit is occupied by an owner or a resident tenant under a minimum 12-month lease.
The law spells out why in its own language, stating its purpose as discouraging "the negative impacts from commercialization and investor-driven acquisition of dwelling units" and promoting "the principal use of dwelling units for residential housing purposes." That's not incidental phrasing. It's the mechanism. The village traded away the stay-length restriction that every other East End town still uses, and replaced it with a residency test that a fully absentee, buy-it-purely-to-rent-it property cannot pass under any of the three tiers.
Why the Stricter-Looking Town Next Door Is Actually the Simpler Buy
This is where the comparison gets useful for anyone weighing Greenport against the surrounding towns as a rental investment.
| Minimum Stay | Owner/Resident Occupancy Required | Annual Permit Cost | |
|---|---|---|---|
| Greenport Village | None, as of Jan. 1, 2026 | Yes, under all three permit tiers | $750 (short-term) |
| Southold Town | 14 nights | No | Roughly $300 per permit cycle |
Southold's rule sounds more restrictive on paper, since it forces a two-week minimum booking. But it doesn't ask who lives in the unit. A property bought purely for rental income, with the owner never present, can still get a permit in Southold as long as it clears the 14-night threshold and passes inspection. In Greenport, that same property, listed with no minimum stay and maximum weekend flexibility, has no permit category it fits into if nobody who holds an ownership or residency stake is ever there.
Riverhead, for reference, currently holds the line at a 30-day minimum stay, the strictest of the three.
What Enforcement Actually Looks Like Right Now
The occupancy rule only matters as much as the village can check it, and that's where Greenport's rollout gets more complicated. The village has been without a full-time code enforcement officer since its previous officer, Alex Bolanos, went on extended medical leave in fall 2024, was later terminated, and filed a lawsuit against the village that remains ongoing. To manage the new permit system, the board brought back a former employee, Kenneth Marulli, as a part-time code enforcement officer starting Dec. 8, 2025, tasked with processing applications and following up on violations alongside his other duties.
Southold Town, by contrast, has spent the past year building out an active enforcement pipeline. The town adopted a tracking program called Rentalscape in 2025 to cross-reference booking activity against permit records, and by mid-2025 the software had flagged more than 400 properties with bookings shorter than the 14-night minimum. In April 2026, the town attorney's office announced it was sending letters to flagged owners, giving them 30 days to either apply for a permit or pull their listing before facing fines.
Put the two side by side and the near-term picture is almost the reverse of what the codes themselves suggest. Greenport's rule is stricter in what it requires, but is currently enforced by one part-time hire managing brand-new paperwork. Southold's rule is more permissive on who can hold a permit, but is backed by software actively identifying violators today. Enforcement risk doesn't track neatly with which town has the tougher-sounding law.
What This Means If You're the One Signing the Application
If the plan is a Greenport property purchased strictly for rental yield, with no part of the year spent living there and no intention of leasing a unit to a long-term tenant, none of the three permit tiers currently accommodate that structure. The flexibility on stay length doesn't open a path around the occupancy requirement. Before writing an offer on anything marketed with rental income projections, it's worth confirming which permit tier, if any, the property and your intended use would actually qualify for.
It's also worth knowing that permits don't transfer with the sale. A new owner has 30 days after closing to apply for their own permit, and a seller's rental income history under the old code doesn't carry forward automatically under the new one. A listing that shows strong past short-term income may be describing a use the current code no longer allows for a buyer whose plans differ from the seller's.
Quick Answers
Does Greenport still require a minimum length of stay for rentals? No. As of Jan. 1, 2026, there's no minimum, but every short-term permit has to fall under one of three occupancy-based categories, so length of stay isn't the limiting factor anymore.
Can I buy a second home in Greenport and rent it out when I'm not using it? That's the intent behind the Owner-Occupied tier, which allows the full unit to be rented as long as the owner occupies it for part of the year. The specifics of what counts as sufficient occupancy are spelled out in the current version of Chapter 103, and confirming eligibility before purchase is worth the time.
Is Southold's 14-day minimum an easier rule to work with for a rental-only property? It doesn't tie the permit to owner or resident occupancy, which is a real difference. It comes with its own enforcement pressure, though, since the town has been actively using tracking software to identify properties booked under 14 nights.
Rules like these are exactly why a rental income projection on a listing sheet and the permit that property can actually carry are two different questions. If you're weighing a North Fork property against its rental potential, The Principi Team can walk through what a specific address qualifies for before you're past the point of backing out. Contact Us.
