Taking its name from one of the most photographed buildings in New York City, the Flatiron district is named for the iconic Flatiron building, which sits on the wedge-shaped intersection of Fifth Avenue and Broadway. In the last two decades or so, the neighborhood has turned itself inside out. Once a renowned center of commerce and fashion, the area is thriving again—but in a new way.

The Flatiron district’s nebulous boundaries include the historical landmark districts of Madison Square Park and Ladies’ Mile, roughly between 7th Avenue and Park Avenue from 14th to 30th Streets.

Flatiron History

In the early 19th century, what is now known as the Flatiron district was mostly open farmland, owned by farmers Isaac Varian, Casper Samler, and John Horn. Nearby, the Madison Cottage—a popular tavern and roadhouse at the time, earned the New York Herald’s description as “One of the most agreeable spots for an afternoon lounge in the suburbs of the city.”

The area might have stayed pasture and field for a few more years, had it not been for the Commissioner’s Plan of 1811, which divided the city into its now famous rectangular grid of streets from 14th Street on up.

The plan included Broadway, which ran in a conspicuous diagonal across the grid, causing odd triangular lots where the thoroughfare cut across the street grid. These irregular bits were made into parks, and have come to be known as Times Square, Herald Square, Union Square and Madison Square. The famous Flatiron building itself sits on a projection of land between Broadway and Fifth Avenue, and looks out over Madison Square Park. Originally set aside as the ‘Grand Parade,” which was to be used for markets and parks, the area at Fifth and Broadway was reduced in size over time, and named for the then President of the United States, James Madison.

In 1836, the Common Council voted to establish the area as a public space, and within a decade numerous houses were built along the north and east sides of Madison Square Park and in the surrounding blocks. The majority of the new residences, sold from parcels of land from the Varian and Samler estates, were built in brick or brownstone, in the Italianate style that prevailed at the time. Ornamentation was relatively sparse, and most were four or five stories tall.

The Civil War Era

By 1860, Madison Square had garnered the reputation as the city’s social center, with wealthy families such as the Haights, Stokes, Schieffelins, Wolfes, and Barlows taking up residence in the neighborhood. These families helped shape the character of the neighborhood, and supported the churches in the area, including the Church of the Transfiguration at One East 29th Street, Trinity Chapel (now the Serbian Orthodox Cathedral of Saint Sava) at 15 W. 25th Street, and the Marble Collegiate Church on Fifth Avenue and 29th Street, all of which are designated New York City Landmarks.

During the Civil War, Madison Park served as a campground for Union soldiers, and the park fell into a state of disrepair. In 1870 however, the city’s Common Council (a forerunner of today’s City Council) voted to finance the renovation of the park. Shortly thereafter—from 1874 to 1876—the park served as an exhibition ground for the arm and torch of the Statue of Liberty in an effort to raise money for the pedestal and construction of one of New York’s most famous modern landmarks.

The prestigious Fifth Avenue Hotel, constructed between 1856 and 1858 at Broadway and 23rd Street signaled the move uptown of many city hotels, and turned the pre-Flatiron area into a new hotel district. Soon the neighborhood was home to many hotels, including the Albermarle House, the Hoffman House, Worth House, St. James Hotel and Victoria Hotel, all built between 1860 and 1870.

Apartment living became fashionable for the wealthy—notably among well-to-do bachelors—in the 1880s. While many of the buildings in the neighborhood were originally designed as single-family homes, the trend produced some apartment buildings that were aimed at this demographic.

More Changes

As the city pushed northward, Madison Square benefited from its central location. The neighborhood’s most famous venue in a growing list of theaters was Madison Square Garden, which was originally the New York and Harlem Railroad depot, located at Madison Avenue and 26th Street. P.T. Barnum, with financing from the Vanderbilts, moved his famous circus to the “Great Hippodrome” in Madison Square Park in 1874. The building was condemned in 1880 and the second Madison Square Garden—this one built by Stanford White—opened in 1890.

In the 1870’s, the Flatiron district gained a reputation for its collection of clubs that catered to men’s organizations. The area saw an influx of mercantile and business interests, and the high-speed elevator made taller and taller buildings possible. By 1900, as business poured into the district, banks began opening up in the area, and the now-famous buildings ringing Madison Square Park were competing for the prize of tallest building in the world. At the time of its completion, the Met Life Clock Tower on the park’s eastern border held the prize.

The Flatiron and Ladies’ Mile

Although not the tallest building in the area, when it was completed in 1902 the Flatiron building was from its inception one of the most noteworthy. Upon its completion, the Flatiron was reviewed in Architectural Record as “quite the most notorious thing in New York and attract[ing] more attention than all the other buildings now going up together.”

Very few buildings have been erected in the area since the Depression—partially because of the efforts of architectural preservationists—and the minimal alterations to storefronts and office buildings leave the area in its early 20th century visage and commercial character.

The area known as Ladies’ Mile gained its Historical Landmark status in 1989. While the landmark boundaries extend a little further into the neighborhood, Ladies’ Mile is chiefly known as the strip of Fifth Avenue south of 23rd Street to 14th Street and back up Broadway and Sixth Avenue to about 21st and 23rd Street, respectively.

Ladies’ Mile was the primary promenade for women who had “nothing to wear”—but plenty of time to shop. The many society balls, events, and parties that took place in the area around the turn of the 20th century required a multitude of accessories, silks, shoes, jewelry and various accouterments to complement a lady’s evening ensemble. This was an era when the same outfit was not to be seen twice in public, and the appetite for new styles was voracious.

The mercantile industry rose to meet the demand, and many of the new buildings that were erected during this time were sure to include a storefront with adequate window space to display the new styles and fashions.

The Ladies’ Mile was not just for ladies and shopping, however. The area was dense with concert halls, theaters, galleries, wholesalers, interior decorators, and the offices of publishers and architects. In fact, it was here that New York first became a world player in the arenas of fashion, publishing, and design.

A Residential Riot

Like many parts of the city, the Flatiron district has seen its share of ups and downs. In the Depression Era, Madison Square Park was occupied by squatters and those displaced by economic catastrophe, and in the bad old days of the 1970s and ‘80s, Madison Square Park had become one of those dark, winding spaces that housed more danger than delight. Most residents chose to walk around it, rather than through it—but as with almost any other Manhattan neighborhood you can name, that all changed with the real estate boom and the subsequent renovation of the park and new developments in the area.

Bordered by the two parks at Madison Square and Union Square, the Flatiron district has recently become a residential Mecca, with large numbers of commercial spaces converting to condo lofts. Leonard Steinberg of Prudential Douglas Elliman reports that the Flatiron district offers residents a vast array of options and entertainment.

“If Flatiron is known for one thing, it is known for its exceptional quality loft space—and some truly spectacular architecture,” says Steinberg.

The rush to convert formerly commercial spaces to multimillion-dollar luxury apartments has engulfed some of the district’s most notable landmarks. The Toy Building on the west side of Madison Square Park has announced that it will soon be going condo. Ian Schraeger of Studio 54 and Paramount Hotel fame is putting up new residential spaces in the clock tower, and many more loft spaces in the neighborhood are being converted into residential units. In short, the area is booming.

The cost of real estate in the area is, as always, dependent upon the specific location, amenities, and size of the space in question. There are two different kinds of apartment in the area, according to Steinberg: the regular and the loft, and many different classes of apartment are available. For condos, you can expect to pay from $1,000 to $3,000 per square-foot for a fabulous prewar loft space. According to Steinberg, co-ops around the Flatiron building start from about $750 to $800 per square-foot, going up to about $1,500 per square-foot. Most of the more recent conversions, the more glamorous buildings, are all condos, so the co-op market prices are a little lower.

Rental studios start at around $1,200 to $1,300 per month. One-bedroom apartments can run about $2,300, and a two-bedroom apartment in a luxury building may go for as much as $7,000 to $8,000 per month.

Faces of the Flatiron

What kinds of people will you find making their home in this richly storied area? “A mixed bag,” says Steinberg, “and all age groups. You’ll find a mix of Wall Street types and artists, much the same as you would find in the Village. There are all kinds of people moving here, partially because of the area’s central location.”

Indeed, a spokesman for the Madison Square Park Conservancy notes that there are many programs for children in the park, as well as art exhibitions and outdoor concerts. The summer is a prime time for park users, and residents sun themselves on a break from work and on weekends.

What draws people to want to live in the Flatiron District? Steinberg sums it up: “With a multitude of shopping, restaurant, and park options, they are ideally situated in Manhattan. Union Square and Madison Square Parks sandwich the Flatiron district. Having two parks is extremely rare, and there is an abundance of markets, food stores, and entertainment. It is an incredibly convenient location for people to live whether their interests or work take them uptown or downtown.”

Denton Tarver is a freelance writer living in New York City.