A townhouse on Macdougal Street With a Secret, Shared Garden

The brick townhouse at 90 Macdougal Street has five bedrooms, four bathrooms, and polished, modern interiors. But the real appeal of the property, which just hit the market asking $8.5 million, is the secret block-long garden behind it, an expanse shared by the residents of the 21 houses surrounding it (one of whom is Anna Wintour).

The longtime owner opted to paint 90 MacDougal purple.
Photo: Zoe Whetherall

The Macdougal-Sullivan Gardens Historic District, which includes 11 rowhouses on Macdougal Street and another ten on Sullivan, is one of the few shared backyard gardens in the city (there’s also Turtle Bay Gardens and, in the East 60s, Jones Wood). The homes have small private backyards beyond which lies the much larger common garden in the middle. Houses there rarely go on the market — there’s also a covenant in bylaws that says current residents have first dibs when a property lists — and 90 Macdougal hasn’t traded hands since 1975, when it was bought by Gloria Naftali, the co-founder of Chelsea gallery Greene Naftali, who died in 2022. The home, painted in a pale lilac shade, is now listed with Leslie Garfield’s Matthew Pravda and Matthew Lesser, who noted that while it’s technically an estate, the home has central air and has been updated over the years. There’s an open parlor floor, a primary suite on the third with more bedrooms above, and a finished basement. French doors on the back of the house open to numerous balconies overlooking the bucolic backyard.

The garden rowhouses have long attracted artists of various sorts. The French composer Edgard Varese, Alexander Calder’s daughter Mary Rower, and Bob Dylan have all lived there. Dylan took up residence in 1969, after visiting the producer John Hammond Sr. (His son, John Hammond Jr., who grew up on the garden, is a blues musician.) The painter Pat Stier lives there now, as does Diego Delle Valle, the president and CEO of Tod’s, and his fashion entrepreneur son Emanuele Della Valle. Baz Luhrmann and Richard Gere are former residents, although Gere, apparently, wasn’t very popular. After he planted a tall privacy hedge along his section of the low common hedgerow, it was, according to the New York Times, “unceremoniously chopped down by the other residents.”

The houses were built in the 1840s and 50s for “the lesser gentry,” as Christopher Gray once put it in a “Streetscapes” column — the properly rich lived in grander houses around the corner on Bleecker. Still, the 20-foot-wide four-story homes were plenty gracious, and the owners respectable types until the area went downhill in the 1880s, at which point many of the homes were broken up into apartments and rooming houses. The communal garden was created in 1921, when a real-estate developer bought up many of the houses, sheared off the stoops, connected the backyards, and turned it into an apartment complex, with owners’ duplexes on the bottom floors and rental apartments above. In the 1960s there was a nursery school for all the young children who lived there, a group gardening day and potluck, trick-or-treating, and Christmas caroling.

Now, nearly all of the houses are single-family and houses trade in the low teens. The  freewheeling, bohemian days are no more, and a professional landscaper now tends to the garden’s trees and greenery. But the garden remains a communal space, uniting these neighbors, at least in theory. “There is still a basketball hoop and a playhouse,” says Lesser. “It’s a really special space.”

The home’s interiors are modern and polished.
Photo: Zoe Whetherall

A bulkhead on the roof lets light into the core of the four-story home.
Photo: Zoe Whetherall

French doors open to little balconies overlooking the gardens.
Photo: Zoe Whetherall

Each home has a small private backyard separated from the communal garden by a low hedgerow.
Photo: Zoe Whetherall

The home, asking $8.5 million, has central air.
Photo: Zoe Whetherall

The house has five bedrooms, four baths, and a finished basement.
Photo: Zoe Whetherall

City records show that it has been owned by Gloria Naftali since 1975. Naftali died in 2022.
Photo: Zoe Whetherall

Other residents of the garden enclave include Anna Wintour and the founder and CEO of Tod’s shoes.
Photo: Zoe Whetherall