Drive down Main Street in Wainscott past Bill and Lisa's farmstand and you'll pass a stretch of open field that looks like it hasn't changed in three hundred years. Grass runs to a treeline, the land dips toward Wainscott Pond, and somewhere past that, the dunes and the ocean. Most people who live here assume that view is locked in now that the town owns it. It isn't, not entirely, and the fight over exactly how locked in it should be has been running in East Hampton Town Hall for almost two years.
The property is 66 Main Street, known to town records and preservationists alike as the John Osborn Homestead. In December 2024, East Hampton Town closed on the 30-acre parcel for $56 million using Community Preservation Fund money, the largest CPF purchase in the town's history. The seller was Ronald Lauder, a neighboring property owner who had bought the land himself for $66 million and agreed to resell it to the town well below market value specifically so it could be preserved. That gap between what Lauder paid and what the town paid is the whole story in miniature: a lot of people wanted this land protected, and they were willing to leave money on the table to make it happen.
What $56 million actually bought
The town's own paperwork lists four purposes for the acquisition: open space, agriculture, historic preservation, and water quality improvement. Three of those point toward keeping the land exactly as it is. The second one doesn't. Agriculture was written into the deal from day one, which means the meadow residents drive past today was never legally promised to stay a meadow forever. That tension between "we bought this to preserve it" and "one of the four stated uses is farming it" is what has kept Wainscott's civic meetings full for the better part of two years.
For most of the twentieth century, the Osborn family did farm this land. Potatoes went in through the 1980s, then strawberries until 1994. After that the fields sat fallow, and what residents now call a meadow is really thirty years of unfarmed grassland reclaiming itself. That distinction matters to the people arguing against reintroducing agriculture: this wouldn't be restoring a working farm so much as introducing an entirely new use to land that has functioned as open space for longer than most current residents have lived in Wainscott.
Two buildings got protected. The land underneath them didn't.
In March 2025, the Town Board unanimously landmarked two structures on the property: the 1904 Louisa Edwards Osborn house and the 17th-century Osborn barn. A third building on the site, a small structure known locally as the playhouse, was left out. So was the land itself. Landmark status in East Hampton applies to buildings, not acreage, which means the meadow, the pond frontage, and the viewshed that everyone actually cares about have no historic protection at all. They're covered only by whatever the management plan says, and management plans can be revised.
Esperanza Leon, president of the Wainscott Heritage Project, has made this argument at nearly every hearing since. "The John Osborn Homestead is not merely a collection of old buildings," she told the Town Board, pushing for the entire 30-acre parcel, not just the structures, to receive historic designation. Her group's position is that protecting the house and barn while leaving the surrounding fields open to future development or intensive farming preserves a shell while losing the actual story.
The fight nobody expected: whether to farm it
The most contested piece of the management plan turned out to be agriculture, and the opposition has been close to unanimous. The Wainscott Citizens Advisory Committee, through chairman Hersey Egginton, formally asked the board to strike active farming from the plan entirely, arguing it would harm both the water quality of Wainscott Pond and the open sightline from Main Street. Jaine Mehring, the Wainscott Heritage Project's vice president, has focused specifically on what farm chemicals and irrigation could do to a pond that a Stony Brook University study, led by researcher Christopher Gobler, found to be nearly the most impaired water body in New York State, behind only one site in Central Park.
There's a physical mechanism at the center of this that's easy to miss if you just skim the headlines. Any working farm on that field would likely need deer fencing to survive, and deer fencing is exactly the kind of visual obstruction that undermines the open vista the whole preservation effort was built around. Councilman Ian Calder-Piedmonte, who is himself a farmer and served as the board's liaison on the draft plan, initially wanted language requiring organic practices struck from the document. The community pushed back hard enough that fencing became one of the flashpoints in the final vote. In late April 2026, the board adopted the management plan as written in a 3-to-2 split, with Calder-Piedmonte, David Lys, and Tom Flight in the majority and Supervisor Kathee Burke-Gonzalez and Councilwoman Cate Rogers dissenting. Agriculture stayed in the plan as a permitted use. It wasn't banned, and it wasn't guaranteed either, since the town has not yet named a licensee to farm or otherwise occupy any part of the property.
Grass or asphalt, and a few other things still unresolved
Farming wasn't the only open question. The draft plan also floated a walking loop through the property, along with parking, water quality remediation work, and even the possibility of duck hunting on the pond side. The one that generated the most unexpected friction was the surface of the proposed path. Residents and even members of the town's own Architectural Review Board pushed back on the idea of paving it. Chip Rae, the ARB's chairman, called an asphalt trail through the meadow "a disaster" waiting to happen to the site's character. As of this spring, the board itself was still debating grass versus pavement, a detail that sounds small until you remember it will determine what the first quarter mile of that view looks like to everyone walking Main Street.
None of this is finished business. Burke-Gonzalez has been explicit that the management plan isn't locked in perpetuity. It can be amended through future public hearings and board votes, which means residents who want the meadow left alone, or who want stricter limits on farming, still have a real avenue to make that case.
You can walk it yourself
The property isn't sealed off while all of this gets sorted out. In the spring of 2025, the East Hampton Trails Preservation Society led a guided walk of the homestead grounds, meeting at Beach Lane by the ocean with Esperanza Leon and Hilary Osborn Malecki, a descendant of the family that farmed this land since the 1600s, on hand to talk through its history. Malecki has described clouds of dragonflies over the pond and meadow birds moving through the grassland, the kind of detail that only someone who grew up on the land would think to mention. That's worth seeing now, while the field still looks the way it has for the last three decades, because the version of this property that exists five years from now depends on decisions the town board hasn't fully made.
If there's one thing worth carrying away from all of this, it's that "preserved" doesn't mean "unchangeable." The town spent a record-setting $56 million to buy this land, and the fine print of how it gets used is still being argued out meeting by meeting. Anyone who cares where that argument lands has a reason to show up at the next Wainscott Citizens Advisory Committee meeting rather than assume the field will simply stay the way it looks from the car window.
For those of you who love this stretch of Main Street enough to want to understand exactly what's happening to it, or who are weighing what it means to put down roots in a hamlet where residents still turn out in force to fight for a viewshed, David Tenenbaum has spent years working the ground between Bridgehampton and East Hampton and is always glad to talk through what's actually happening in Wainscott, meadow politics included. If you'd rather see the neighborhood in person than read about it, reach out anytime to schedule a showing.
