New York’s urban landscape is constantly changing, with thousands of new buildings popping up throughout the city at a speedy pace. But in order to make space for those shiny new projects, old structures must sometimes come down—and sometimes, historically significant buildings are lost in the pursuit of the new.

The Landmarks Preservation Commission is tasked with determining which New York City buildings (and, in rarer cases, outdoor areas) are worthy of protection, and civic groups like the Historic Districts Council, New York Landmarks Conservancy, and Greenwich Village Society for Historic Preservation also keep tabs on structures that are endangered.

Those groups have succeeded in preserving iconic NYC buildings like 550 Madison Avenue, the Philip Johnson-designed Postmodern tower, which became a landmark this year. But historically significant structures can still face the wrecking ball—like the the stately rowhomes along Brooklyn’s Admiral’s Row, which were torn down in 2016

Earlier this year, Curbed columnist Nathan Kensinger took a look at 10 buildings across the city that were slated for demolition, including the South Street Seaport’s New Market Building—which will likely be gone by year’s end—and the old Essex Street Market, which will be replaced with senior housing after its vendors relocate to a new market.

And the buildings on this list face an uncertain future—and, in a few cases, almost certain destruction. Each stands as a clear reminder of some aspect of the city’s past, but also as an obstacle to builders of its future. Enjoy them while you can; they may not be around much longer.

1. Union Carbide Building

Earlier this year, JP Morgan Chase and the de Blasio administration announced the first major project to come out of the Midtown East rezoning: a 70-story skyscraper that will rise at 270 Park Avenue, intended to be the banking giant’s new HQ.

But in order to construct the new building, the existing structure—a 52-story tower designed by Gordon Bunshaft and Natalie de Blois of Skidmore, Owings & Merrill—will need to be demolished. The news sparked an outcry among architecture buffs, including Curbed critic Alexandra Lange, who said it is “the worst form of shortsighted to throw this building away.”

“It’s a 53-story building that they’re demolishing to build a 70-story building. That makes no sense,” says Simeon Bankoff, the executive director of the Historic Districts Council. “As an urbanist, as someone who cares about New York City, and cares about cities, it just strikes me as some sort of monument to conspicuous consumption that’s unsustainable.”

Unlike other midcentury buildings in the Midtown East rezoning area (such as Lever House or the Citicorp Tower), the Union Carbide tower is not a landmark, and the Landmarks Preservation Commission has no plans to change that.

2. S.W. Bowne Grain Storehouse

This 19th-century warehouse on the banks of Gowanus Canal has faced an uncertain fate for several years. It was purchased by the Chetrit Group (under the business name of CF Smith LLC and Red Hook Developers Holdings LLC) in 2007, but little has been done to the site since then. As Curbed columnist Nathan Kensinger reported in 2017, “the entire campus is currently being left wide open to the elements.”

It suffered another blow earlier this summer, when a two-alarm fire—which the FDNY ultimately deemed suspicious—tore through the site. In the months since, little information has come to light from either the FDNY or the owners; a spokesperson for City Council member Carlos Menchaca says his office is awaiting an update from the fire department, and hope to move forward with any necessary actions.

A group of neighborhood residents, called the Gowanus Landmarking Coalition, is pushing for the LPC to designate the Bowne storehouse (along with other area buildings—we’ll get to those in a bit); previous efforts by other groups, however, have failed.

3. St. Denis Hotel

The 160-year-old building at the corner of Broadway and East 11th Street may not be long for this world: The former St. Denis Hotel is slated for demolition and is likely to be replaced with a 12-story office building. Scaffolding has already gone up, and demolition plans are on file with the Department of Buildings (though not approved as of press time.)

But activists are determined to keep that from happening: The Greenwich Village Society for Historic Preservation has been leading the charge to save the St. Denis, holding rallies and generally raising awareness of the building’s history. (It was designed by James Renwick, who’s also responsible for the Gothic Grace Church across the street.)

That may be helping, as City Council member Carlina Rivera has asked the LPC to once again consider the building for landmark status, “due to the neighborhood’s vocal support for the building and the history behind both its architecture and the former residents who passed through its doors,” according to a spokesperson.

The LPC had previously decided not to consider the building because it has been “significantly altered,” according to an agency spokesperson.

4. 99 Ryerson Street

Poet and noted Brooklynite Walt Whitman only lived at the home at 99 Ryerson Street for a short period, but preservationists contend that it was an important one—he reportedly finished Leaves of Grass while staying at the home. Despite this, it’s not a New York City landmark, and there are fears that it will eventually meet the wrecking ball, especially as development at the nearby Brooklyn Navy Yard ramps up.

“That section of Wallabout is getting more gentrified and you see more and more people being interested in living there,” says Bankoff. “It is a really attractive development site. And without the protections of landmarking, truly it will be gone.”

The LPC declined to landmark the building in 2017, but this summer, activists renewed the push to protect it.

5. Gowanus industrial buildings

Separately from the S.W. Bowne Grain Storehouse, the Gowanus Landmarking Coalition is seeking to protect more than two dozen industrial buildings in the Brooklyn neighborhood. The collective, which includes HDC as well as several community groups, believes that the coming rezoning of the neighborhood will put these buildings—some of which date back to the 19th century—at risk.

“Our concern is that a firestorm of rezoning is coming,” Bankoff said at the time. “And if we don’t act—if the city does not act—before the rezoning to preserve some of these older structures, there won’t be anything left. All we will have is a bunch of postcards.”

The endangered structures included in the list of proposed landmarks include the Gowanus Station building on Butler Street, which may be demolished to facilitate cleanup of the toxic canal, and a former stable on Carroll Street that’s currently home to the bar Lavender Lake.

6. Tin Pan Alley

A stretch of low-rise buildings along West 28th Street was once home to some of the most influential songwriters and music publishers of the early 20th century. Songs like “Take Me Out to the Ball Game,” “God Bless America,” and “Sweet Georgia Brown” were composed there, and some of the Great American Songbook writers (including Irving Berlin and George Gershwin) worked out of these buildings.

Despite this, they don’t have landmark protection—and with development encroaching throughout Midtown and the area thats come to be known as Nomad, these buildings could potentially be threatened. “They’re not small buildings, but they are small for what the city seems to want to do in that area,” Bankoff says. “The city has been slowly looking to eradicate commercial enterprise in Manhattan—in terms of the Garment Center, in terms of the flower market—[and] people are going to start looking for highest and best use, in the sense of being the most profitable use. A series of four or five story buildings is not going to be good enough.”

Preservationists have been seeking landmark protections for Tin Pan Alley for more than a decade, with the most recent effort—a “Save Tin Pan Alley” day rally—happening last October.

7. 206 Bowery and 22 East Broadway

Two Federal-style houses, both dating back to the early 19th century, remain mostly intact on the Lower East Side, but their days could be numbered. Despite a concerted effort by preservationists to protect the buildings —as well as the support of the local community board—the LPC is no longer considering the structures for landmark status.

Thanks to a change in the Landmarks law, because they had been stalled in the designation process for several years—the LPC’s first hearing on them was back in 2010—they were taken out of consideration last year. The buildings “are not among the agency’s current priorities, but this does not preclude their consideration by the Commission at a future date,” an LPC spokesperson said.

While there is no immediate threat to either building at this time, their lack of protection makes them more vulnerable to encroaching development. (A former flophouse on one side of 206 Bowery already went condo.)