A new development battle is under way that centers on whether the city’s Landmarks Preservation Commission is willing to expand the boundaries of the Upper East Side historic district to include almost 200 more buildings, a number of which could be demolished any day now to make way for new construction.

The Department of Buildings said it is reviewing a demolition permit for the Kean House, a historic structure originally built in 1880 at East 65th Street and Lexington Avenue, just yards outside the perimeter of the landmark boundaries which were established in 1981.

“There is so much urgency because Lexington is the main street of the Upper East Side, and has a sense of place that you don’t have on Park Avenue and on Third Avenue, which is now like a canyon of towers,” the executive director of the Friends of the Upper East Side Historic Districts, Seri Worden, said. Ms. Worden said more than 120 residents attended a local community board meeting Monday night, at which a resolution was drafted to pressure the Landmarks Commission to reconsider the boundaries of the protected historic district, which extends between East 59th and 79th streets and jigsaws out along the eastern edge of Central Park East to Lexington Avenue.

A spokeswoman for the Landmarks Commission, Elisabeth de Bourbon, said earlier this summer the commission staff had considered Kean House for individual landmarking designation, but decided it did no meet the criteria. Ms. de Bourbon did say the commission was “actively looking at the district,” but could not give an accurate timeframe for when its boundaries could change.

The questions surrounding the proposed expansion of the Upper East Side historic district and the fate of the Kean House are but the most recent examples of the arbitrary nature of landmarking, which, with the single flick of a pen, can set entire swaths of the city into amber. “It happens all the time. Boundary issues are always the hardest element of designation,” the executive director of the Historic Districts Council, Simeon Bankoff, said. He added that he was still smarting over the recent landmark designation of the NoHo District, which he says excluded a couple of small buildings on the edge.

Area residents have used Friends of the Upper East Side to successfully lobby against a number of development proposals, most recently developer Aby Rosen’s plan to build a residential tower above the Parke-Bernet Gallery at 980 Madison Ave., and the Whitney Museum’s plan for a new gallery on the Upper East Side two years ago.

Council Member Daniel Garodnick, whose district includes the Upper East Side, said the idea of expanding the historic district — which he supports — was only the latest in a string of landmarking boundary issues he has confronted.

Mr. Garodnick also supported local residents who asked that a strip of buildings along East 93rd Street be reconsidered during the Carnegie Hill historic district expansion in the 1990s. The Landmarks Commission did not include the buildings.

“The hardest cases are always those where you have to say no,” Ms. de Bourbon said.

According to a building permit, the developer Davis Development has plans for a 50,000-square-foot residential tower that would be somewhere between 16 and 18 stories tall at the site where the Kean House currently stands. The developer was unavailable for comment yesterday.

For preservationists aiming to save the Kean House — which was originally built as two brownstones in 1880 and then transformed in 1922 into a residence and artist’s studio for an artist and architect, J. Stewart Barney — there is little to be done once the buildings department issues its permits.

Local resident Marvin Berman said he was in favor of expanding the historical district and opposed to the demolition of the Kean House — a building he has lived next to for the last 40 years — but not for aesthetic reasons.

“I am not an architectural or aesthetic maven, but it is somewhat run down,” he said. “I think it mostly matters to people because they see it in a different light. They see the uniqueness, the irreplaceable factor, and that is all true. But aesthetically, it’s just another building.”