Coming in at just 63 feet long, Edgar Street at Trinity Place is the shortest street in the city, according to data from PropertyShark (though Michelle and James Nevius, authors of Inside the Apple: A Streetwise History of New York City, claim that Edgar Street is a few feet longer than Mill Lane). It was named for shipping magnate William Edgar. Technically, Edgar Street is actually two streets, thanks to a traffic meridian that divides it, compensating somewhat for its shortness in wideness. 

By a few feet, Mill Lane would seem to get the trophy for shortest street in Manhattan, though PropertyShark data says otherwise. Address-less, this blip of a street was named Mill Lane in 1664, previously having been known as Elliot's Alley. 

So much has happened on one of Manhattan's smallest streets that the Landmarks Preservation Commission gave Weehawken Street its own historic district. Indeed, the street has been host to much maritime history, as well as, according to ScoutingNY, more than its fair share of urine. The street runs parallel to West Street between Christopher and West 10th, and it was once part of the Newgate State Prison (1796-97) and a product market in the mid-1800s.

This tiny addition to the Manhattan street grid only has three buildings on it! According to Forgotten NY, York Street is "the only street in Manhattan named for its original British namesake": the Duke of York. It’s also home to a 32-unit condo building, pictured here.

Jones Street may be miniature, but this one-block long road has been the filming site of multiple movies thanks to its quintessential West Village charm. (It also, more famously, was featured on the cover of Bob Dylan's 1963 album The Freewheelin' Bob Dylan.) The road predates 1789, and its namesake, Doctor Gardner Jones, was related to the namesake of Great Jones Street.

One of the oldest streets in New York is Minetta Street, a small block with a slight curve located in Greenwich Village. (It intersects with the slightly busier, and rather small, Minetta Lane.) Named after the Minetta Brook that used to run through the neighborhood, the street was once considered dangerous because of the saloons frequently inhabited by gangs. The street was also the set of the Al Pacino film, Serpico.

Chinatown has many alleys and side streets, and one of the littlest is Mosco Street, a street lined by small businesses on each side. Mosco Street was originally called Cross Street of the Five Points neighborhood during the 19th century and was known as one of the most dangerous slums in the city.

What's cuter than a miniature street? One that comes with miniature doors to match. Dennet Place is a one-block street in Carroll Gardens made up of houses, nicknamed "Hobbit Houses," with doors that are "roughly four-foot tall" at the ground level. The enclave is home to "a tight-knit collection of Italian-American families," according to the Times.

More super expensive quaintness and painfully adorable converted carriage houses can be found on this itty-bitty Brooklyn Heights side street. Grace Court Alley was originally home to the horse stables of the Remsen Family, who lived nearby; today, its converted homes sell for millions of dollars.

Yep, it’s another Brooklyn Heights side-alley that’s lined with pricey carriage houses, including, quite possibly, Brooklyn's most charming home. The dead-end street looks like something out of a movie; there are no sidewalks and no traffic, so you’ll often find neighborhood kids playing in the street. 

Built in 1922, Pomander Walk, one of Manhattan's best-kept secrets, stretches between 94th and 95th Streets, and features 16 of the most charming homes in New York. Locals know it as "The Walk," and residents are known to house-swap. Pomander Walk's creator originally planned to raze the houses and build a hotel, but he died before that plan could happen.

St. Charles Place and its neighboring St. Francis Place are adorably anomalous additions to Central Brooklyn's grid. Lined with townhouses, these two one-block-long streets are just off bustling Franklin Avenue in Crown Heights, but they are remarkably quiet and feel secluded.

This one-way, tree-lined side street is right off of Metropolitan Avenue in Williamsburg, but it’s not exactly on the radar of the typical Williamsburg crowds. "It's like a sanctuary," one resident told the Times, “and it feels like everything else in Williamsburg is evolving except here. You either don't get it or completely fall in love with it."

At just one block long, Beak Street is one of Manhattan's shortest named streets. The street ends where Inwood Hill Park begins.

Once a quiet little cul-de-sac, Tulfan Terrace in Riverdale has seen big changes since the development of new condos nearby. Single-family houses that date back decades face a high-rise residential building, which replaced some of the street’s old homes. (The development wasn’t without controversy, either.) But despite that, the street is still plenty charming—and at barely a block long, plenty small.