With the summer season fast approaching and the village’s storefront vacancies still conspicuous, the Greenport Business Improvement District convened a meeting last week that local business leaders hope will prove to be a strategic inflection point for the village.
The BID’s plan, still in its early stages, is a partnership with a team of outside commercial brokers to help Greenport do what it has struggled to do on its own: systematically fill empty storefronts and reshape the broader economic future of the village.
“This is not going to be an overnight thing,” BID President Rich Vandenburgh told attendees at the outset. “This is going to be a concerted effort to try to change the narrative — that Greenport is open for business.”
A coordinated push
The BID’s primary mission, tackling vacancies, led to the selection of Helmsley Spear, a Manhattan-based firm with experience in large-scale urban revitalization efforts.
Their pitch, delivered by firm owner Kent Swig and his team, was presented as a coordinated redevelopment strategy. It will include market analysis, a new branding campaign and a sort of matchmaking operation between landlords, tenants and capital.
“Our goal here is very, very simple,” Swig said. “To work with the community, through the BID, to make Greenport a more livable, workable and financially better place for everybody.” He said the firm isn’t being compensated.
The firm, which is volunteering its time, according to Swig, plans to conduct a full diagnostic of the village’s commercial ecosystem. This will include meeting with local brokers, surveying landlords, cataloging vacancies and identifying what kinds of businesses are missing.
The objective is not just occupancy, according to broker Neil Ergezer.
“We wouldn’t bring another coffee shop, another T-shirt shop or another brewery,” he said. “We don’t want to cannibalize the existing businesses here.”
Instead, the focus is on categories that could stabilize the village year-round, including specialty retail, wellness and fitness, medical services, education-related uses and artist studios — all businesses that generate consistent foot traffic beyond peak tourist months.

Marketing a village, not just its vacancies
Central to the plan is a coordinated marketing push.
The firm outlined a strategy that includes public relations campaigns, targeted outreach to brokers across the tri-state area, direct tenant recruitment and, with some investment from the BID, a heavy emphasis on digital visibility, particularly search engine optimization and paid placement.
“If you’re halfway down on Google, you don’t exist,” Ergezer said, describing plans to ensure that Greenport-related searches, including festivals, events and commercial opportunities, surface prominently online.
The idea is to sell Greenport as a place to do business.
“We’re not going to be going out there saying, ‘Look at the vacancies,’” Swig said. “This is going to be a positive story about the area.”
The business community is particularly sensitive to the current perception of a village in decline. Some at the meeting noted that even a small number of dark storefronts can shape that perception.
“It only takes one customer pulling on a locked door” to undermine the notion that the Greenport business community is vibrant, said Rena Wilhelm, co-owner of The Weathered Barn, which is celebrating 15 years in the village.

The year-round problem
Filling space is a visible fix. Sustaining businesses through the winter months is a harder, less visible problem, one tied to workforce housing, staffing shortages and the basic economics of operating in a seasonal market.
Several attendees pushed the BID to address those issues in parallel, including calls for job fairs, centralized hiring resources and broader conversations about labor and retention.
Another challenge is rental rates. Village Mayor Kevin Stuessi was blunt about landlords whom he said won’t budge on price.
“Many landlords have very unrealistic expectations,” he said, describing deals that have fallen apart over relatively small monthly gaps.
David Sargoy, director of Helmsley Spear’s commercial real estate division, said the solution to stalled negotiations is often mathematical, and involves laying out the time-value cost of vacancy and the months of lost rent that can never be recovered.
“A lot of times, when we put it on paper and do an analysis, they look at it and go, ‘Oh, you know, you may be right.’ … You’ve got to get the emotion out of the equation.”
But even that approach has limits.
Complicating matters further is what Ergezer described as lingering “Covid-itis” — owners who purchased or refinanced properties at elevated pandemic-era prices. These owners are now reluctant to adjust expectations downward.
Next steps
The next phase of the initiative will focus on data gathering and plan development over the next 60 days.
Helmsley Spear will conduct individual meetings with local brokers, landlords — both with and without representation — and tenants to collect detailed input on vacancies, leasing challenges and desired business types.
Those findings will be compiled into a formal business and marketing plan that will include public relations, social media, SEO and targeted tenant outreach, to be presented to the BID for review and approval. All external messaging will be coordinated with the BID before release, according to the plan.
The firm will then begin identifying and recruiting prospective tenants, and work to match them with available spaces, including smaller or shared locations. In addition, it will engage directly with landlords to present financial analyses aimed at encouraging market-based lease and sale terms.
Helmsley Spear intends to educate prospective tenants on financing options, including SBA-backed loans, and assist in structuring deals.
The BID will designate a point of contact to coordinate communication. The firm will also work with village officials to identify priority sites, target specific uses for key vacancies, engage owners of difficult properties and provide ongoing updates throughout the process.
Call for ‘dramatic’ action
Meanwhile, former village mayor Dave Kapell, in a statement read at the April 23 Village Board meeting, argued that Greenport’s economic challenges are the direct result of policy decisions made by the current administration, pointing to what he described as an erosion of the village’s commercial tax base.
He cited a 2023 commercial development moratorium and subsequent rezoning of the business district as creating uncertainty and increased costs that have effectively stalled new investment downtown. As a result, Kapell said, vacancies have persisted, commercial values have declined, and more of the tax burden has shifted onto homeowners, worsening affordability and making it harder to attract and retain working families.
Kapell called for what he described as “dramatic” action, including the potential use of eminent domain to take control of long-vacant, high-profile properties such as the Arcade and portions of 110 Front St. and redevelop them with ground-floor retail and affordable housing above.
He argued that the village should take a more aggressive role in driving redevelopment and restoring investor confidence, warning that without decisive intervention, the current trajectory will lead to continued economic decline.



There’s the issue with highly restricted short term rentals. I cannot understand how having visitors/tourists come for an affordable weekend doesn’t help all local businesses. More foot traffic brings more business for everyone, from florists to fishermen.
Yet, to force two-week minimum rentals on those wishing to share their homes with weekend visitors seems to cut off the legs of these potential customers. They would happily browse the town, buying 2nd hand or custom items, munching fine chocolates, great bbq and fresh oysters, checking out artisanal vinegars, hot sauces and beer, enjoying custom cocktails, fine dining and family dining, attending local concerts, movies and museums and so much more, if they could afford to sleep over.
How many closed storefronts does it take for the town to recognize the need for affordable accommodations for our visitors?