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10 Most Charming Spots in the Greenwich Village Historic District

This year marks the 60th anniversary of the Landmarks Law, which for the first time allowed buildings, neighborhoods, and sites to be preserved through landmark designation in New York City.

Designated on April 29, 1969, the Greenwich Village Historic District is one of our city's oldest and largest historic districts. At over 2,200 buildings and 100 blocks, it covers much (but not all) of Greenwich Village between University Place and Washington Street, 13th Street and West 4th Street/St. Luke's Place. Its continuing preservation and oversight remains at the core of Village Preservation's mission, along with that of the 15 other historic districts, over 100 individual landmarks, and eight interior landmarks designated in our neighborhoods since — you can view an interactive timeline of all of these designations here.

The Greenwich Village Historic District is undeniably charming — so much so that it’s virtually impossible to come up with a top-10 list of its most alluring architectural gems. But with no insult to sites not included, here is one run at 10 of the most charming sites you’ll find in this extraordinarily quaint historic quarter.

ByVillage Preservation logoVillage Preservation
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6 Washington Square North
6 Washington Square North icon

6 Washington Square North

San Francisco has its painted ladies on Alamo Square, and New York has these lyrical red brick houses on Washington Square. Built in 1832 to house New York’s wealthiest families, they were immortalized in Henry James’ “Washington Square” and Edith Wharton’s “The Age Innocence.” “The Row” as it is often called is considered the finest collection of Greek Revival houses in New York, nearly all of which maintain their original iron fences in front and stone Greek Revival entryways and stoops. Though the houses appear remarkably intact today, all is not as they seem. Numbers 7 through 13 were actually demolished behind their facades (which were also altered) in 1939 when they were combined and turned into an apartment building. None are still houses, as most are owned and occupied by NYU.
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64 Washington Mews
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64 Washington Mews

This charming back alley is lined with quaint structures. While popular lore says these were built as stables for the fine homes they bordered, on Washington Square North and 8th Street, not all is what it seems here. While some of these structures were indeed built as stables, others were actually automobile garages, and some were built as apartments from the beginning, merely mimicking the “stable” look of their neighbors. Washington Mews is gated at both ends, though the gates are generally left open to allow public access. Nearly all of its buildings are owned or occupied by NYU.
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MacDougal Alley
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MacDougal Alley

MacDougal Alley, on the other hand, is almost always locked at its western end, and the eastern end is permanently blocked by the mass of the large white-brick apartment building at 2 Fifth Avenue. Some of its buildings are in fact residences, while others are extensions of the New York Studio School on 8th Street or the NYU-occupied houses on Washington Square.
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Jefferson Market Library (formerly Courthouse)
Jefferson Market Library (formerly Courthouse) icon

Jefferson Market Library (formerly Courthouse)

The Jefferson Market Library, constructed in 1874-77, was “one of the ten most beautiful buildings in America,” according to a poll of architects conducted in 1885. The Ruskinian Gothic structure, originally a courthouse, is considered one of the finest examples of High Victorian architecture in America. It was designed by Frederick Clarke Withers and Calvert Vaux. When built, the courthouse was part of a complex of buildings that included a prison and a market, which occupied the remainder of the trapezoidal block upon which it is located. The building’s quirky, eccentric design has long been beloved by Villagers. So much so that they rallied mightily in the 1950s and ’60s to save the building from demolition and have it repurposed as a library, one of the signature preservation victories in New York after the tragic loss of the original Penn Station.
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Women's House of Detention
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Women's House of Detention

The Women’s House of Detention, built in 1929, was an Art Deco behemoth intended to embody a more enlightened approach to incarceration. It soon became known for its horrible conditions, the abuse suffered by detainees, and the loud and sometimes vulgar interactions between prisoners and passersby or visitors on the street outside (the jail had operable windows). In 1973 the “House of D,” as it was sometimes called, was demolished to make way for the bucolic and pastoral Jefferson Market Garden, a stunningly green oasis footsteps from the hubbub of Sixth Avenue. Its verdant plantings are maintained by a volunteer community group, and while fenced off, the grounds are regularly open to the public for its enjoyment.
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12 Gay Street
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12 Gay Street

Tiny one block long Gay Street attracts as many visitors for its delightfully intimate scale and architecture as it does for its curiosity-inducing name. Laid out in the early 19th century, the diminutive crooked street features federal-style houses on its west side built in the 1820s and Greek Revival-style houses on its east side built in the 1830s. But it’s not just these quaint early 19th century houses which make the street so beloved, the converted factories at its northern end, and the setback wedding cake top of One Christopher Street which hovers over the bend in the street when viewed from the south, all add to the street’s picturesque and romantic feel. While located just feet from the Stonewall Inn, the birthplace of the modern LGBT rights movement, the street’s name is merely a serendipitous coincidence.
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Grove Court
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Grove Court

Perhaps the most photographed site in Greenwich Village and its historic district is the delightfully surprising Grove Court. Like many streets in the Village, Grove Street east of Hudson Street bends, thus leaving a gap between the houses at numbers 10 and 12, with an unusually deep opening behind them. Filling that space is Grove Court, a collection of tiny houses behind a private gate and triangular courtyard. Built in 1852-54 as workingmen’s cottages on the rear yards of the 1820s Grove Street houses, these are now among the most sought-after residences in New York – at least for those who are willing to live in less than 1,000 square feet.
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39-41 Commerce Street
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39-41 Commerce Street

The twin houses at 39 and 41 Commerce Street are, like many sites on the list, the subject of considerable lore, not all of it true. Originally built in 1831-32 by milkman Peter Huyler, the houses are often reputed to have been built for sisters who refused to speak to one another, and insisted upon a wide yard separating their homes. In fact, in the early 1830s when this area was first being developed, a yard or open space around houses was neither uncommon nor necessarily indicative of a family dispute. What is unusual is that unlike many of the other open spaces in the Village, the yard here was never built upon, for reasons not entirely clear.
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75 1/2 Bedford Street
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75 1/2 Bedford Street

75 ½ Bedford Street was built on what was one of those courtyards or alleyways between houses that were once commonplace in this area, but have almost entirely disappeared. The houses to 75 ½’s north and south were built in 1799 and 1836, respectively. By 1873, when this neighborhood was transforming from a genteel middle-class suburb to a teeming immigrant district, the land between the two houses had been sold to Horatio Gomez, who erected the nine-and-a-half-foot wide house we see on the site today. The steeped Dutch gabled roof dates to this era, while the casement windows, associated with artists’ studios, date to a 1920s renovation when the neighborhood was transforming again to attract writers and painters.
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75 1/2 Bedford Street
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75 1/2 Bedford Street

One of the first occupants of the reborn house was none other than Pulitzer Prize-winning Village poet Edna St. Vincent Millay, who lived here from 1923-24, just after she published her famous poem “My candle burns at both ends.” The house is known as the narrowest in the Village and thought by some to be the narrowest in New York City, though there is some dispute about that claim.
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Northern Dispensary
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Northern Dispensary

One of the charming quirks about Greenwich Village is its meandering, eccentric street pattern. The confusing and often seemingly erratic pattern emanates from the continued existence of streets laid out prior to the Manhattan Street grid based upon family farms and relationship to the Hudson River waterfront and the imposition of standard gridded streets on top of them in some locations. The renaming or numbering of old streets to try to reconcile the two further adds to the confusion, by for instance resulting in West Fourth Street at some points running north of West 12th Street. But perhaps no idiosyncrasy of the Greenwich Village street pattern is more charming than the peculiar fluke of Waverly Place intersecting with itself.
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Northern Dispensary
Northern Dispensary icon

Northern Dispensary

Adding to the curious appeal of this quirky corner is this building. The triangular (trapezoidal, actually) Northern Dispensary, erected in 1827, is one of Greenwich Village’s strangest mysteries. The building has been empty for more than 30 years but has a colorful past. Built on land donated by the city with the stipulation that it only serves the indigent poor who could not afford medical care, it was known as the “Northern Dispensary” because it was then at the northern edge of New York. One of its most famous patients was a down-on-his-luck Edgar Allan Poe, who came in 1837 complaining of a winter cold. From the 1960s through the 1980s it was a dental clinic, but it shut its doors when it refused to treat patients with AIDS. The Archdiocese of New York then purchased the property and sought to locate a hospice for people with AIDS in the building, but that plan was scuttled. In the late 1990s, the building was sold to William Gottlieb, who died a year later. His family is yet to develop or occupy the historic structure.
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3-17 St. Lukes Place
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3-17 St. Lukes Place

The southernmost street in the Greenwich Village Historic District is no doubt also one of its most picturesque. The one block of Leroy Street between Seventh Avenue South and Hudson Streets not only has a special name, but a special character, complete with a gentle bend in the street, a lyrical arrangement of Italianate houses built as an ensemble between 1851 and 1854, and a shaded park across the street. The 15 brick houses with prominent brownstone trim, decorative ironwork fences, and grand stoops have sheltered some prominent residents over the years. The revolutionary Max Eastman lived at no. 11 in 1920, while Theodore Dreiser began writing “An American Tragedy” while living at no. 16 in 1923. “Gentleman” James “J.J.” Walker (for whom the park across the street, a cemetery in the 19th century, is now named) lived at no. 6 in 1926 when he was elected Mayor. The celebrated poet Marianne Moore lived at no. 14 in the 1920s, while the artist Paul Cadmus scandalized the art world in 1934 while living at no. 5 with his homoerotic painting “The Fleet’s In.”
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