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Home of the iconic 1902 Flatiron Building (the one that looks like a big sliver of skyscraper pie), at the intersection of Fifth Avenue and Broadway, this district pulses with a cool, very urban energy.  It was the first center of the pre-2000 NYC Internet start-up era — Silicon Alley – and retains that creative edge as the tech revolution has spread throughout the city. The Ladies’ Mile Historic District, a 28-block landmark area, was once the prime department store shopping destination for proper ladies at the end of the 19th century. Those fine old cast-iron and beaux arts buildings are now repurposed into new retail hubs – especially home and design stores. On 23rd Street new local and organic restaurants are opening by the day; Eataly (say it; get it?) is food purveyor heaven. The lovely Madison Square Park has both large and small dog parks. Union Square’s fabulous farmers’ market is one of the top attractions in a city full of them.

What's There

A special sense of cozy community, centered in Madison Square Park.

The Vibe

Unpretentious, solid New York.


Meeting somebody special under the ornate 1909 sidewalk clock outside 200 Fifth Avenue. Very retro Hollywood.

What's Not There

A noisy night life.

Boundaries14th St to 23rd StLexington Ave to 6th Ave Population Density 136,697
Flatiron Listings