Upper portion of the Flatiron Building in New York in...

Upper portion of the Flatiron Building in New York in summer, against a blue sky, 2018. Credit: Getty Images/Koldertsov ALEX

The only constant in New York is change, as Sam Roberts makes clear in the lively thumbnail histories he attaches to more than two dozen exemplary structures in his book "A History of New York in 27 Buildings" (though three are not actually buildings).

The 18th century Federal Hall in which George Washington took the first presidential oath was razed and replaced by a custom house, which was later turned into a branch of the Treasury, then housed government agencies ranging from the Interstate Commerce Commission to the Coast Guard before being declared a national historic site. The Domino sugar refinery was revamped as office and apartment spaces, after briefly displaying an 80-foot-long sugar sculpture by Kara Walker. A.T. Stewart’s glamorous Marble Palace, model for every department store that followed, was converted into a warehouse, then headquartered a newspaper, then municipal offices. Pier A once jutted into a harbor clogged with freighters and ocean liners, deteriorated for decades while commercial shipping declined, and is now topped by a fancy restaurant suitable for a waterfront devoted to leisure and recreation.

Even buildings that continue to fulfill their original function have seen change, Roberts reminds us. The Apollo Theater, built as a burlesque house in 1914, became a showcase for African-American performers as Harlem became the most famous black neighborhood in America; today, the theater continues to celebrate African-American artists and host its famous weekly Amateur Night while the area around it sees an influx of gentrifying white residents. No longer do 100 long-distance trains depart each day from Grand Central Station now that transcontinental travel is largely by plane, but its majestic public spaces continue to welcome a daily influx of  several hundred thousand commuters—a term that was coined, Roberts notes, “after the New York Central popularized the practice of commuting the cost of single rides for  monthly passengers.”

Those sorts of fun facts abound in “A History of New York in 27 Buildings.” (A personal favorite: the brownstone at 123 Lexington Ave. where Chester A. Arthur was sworn in as president in 1881 is now the enormous Indian spice and grocery store Kalustyan’s.) Yet the book’s casual, anecdotal tone masks considerable intellectual rigor. Emulating the approach he took in ”A History of New York in 101 Objects,” the author chose monuments he deemed “emblematic of a transformational economic, social, political, or cultural event or era.” This broad mandate allows Roberts, former urban affairs correspondent for The New York Times and host of the podcast “Only in New York,” to consider everything from the city’s water-supply infrastructure (the High Bridge on the Harlem River) and subway system (the Stanford White-designed Powerhouse) to the ever-vexed relation of the other boroughs to Manhattan (Brooklyn’s Bossert Hotel).

Roberts chronicles the histories of his chosen monuments in loosely chronological order. He begins with the 17th century Bowne House, whose owner permitted Quakers to worship there in an early demonstration of the city’s tradition of religious tolerance. He ends with 60 Hudson Street, Western Union’s 1930 flagship building, where pneumatic tubes “are now packed with bundled copper wire and fiber optic and coaxial cables” to serve the new digital economy. Public housing, the banking industry, Broadway, and the art market are among the other aspects of New York life he characterizes through individual edifices, each one thoughtfully chosen and vividly depicted.

The book is necessarily highly selective and also includes the Flatiron Building, the Lyceum Theatre, City Hall, among others. Still, it seems odd not to have anything constructed after 1936. (Hunter College Gymnasium in the Bronx, makeshift site of the first session of the United Nations Security Council in 1946, was built after 60 Hudson Street, but Roberts covers it three chapters earlier.) Surely the Brooklyn Heights Promenade, an exemplary urban pushback against the post-World War II mania for highway building, deserves a spot as a monument to New Yorkers’ love of walking. Also, given the current ferocious debate over whether it should be closed while the Brooklyn Queens Expressway it was built to cover is repaired, the Promenade demonstrates the complex issues raised by each shift in the city’s ever-evolving landscape. One of the recent super-skinny high-rises designed for super-rich foreign tenants could serve as a painful object lesson in New York’s inability to deal with its affordable housing crisis.

Each reader is likely to think of a meaningful structure that should have been included, and that’s just what Roberts wants. His declared goal is “to stimulate debate”; he invites readers to submit their own lists. Meanwhile, his own list provides much food for thought and an enjoyable portrait of New York as embodied in 27 key landmarks of its built environment.

A HISTORY OF NEW YORK IN 27 BUILDINGS, by Sam Roberts, Bloomsbury, 304 pp, $28,

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