Why Madonna Left The Upper West Side For A Roach Motel

Jack Isquith
4 min readMar 16, 2017
Madonna Comes To New York

Madonna came to New York from Detroit in 1978. For the first two weeks here, she stayed in a spare bedroom at 270 Riverside Drive, Apt. 3B, with Josh Braun her bandmate in the short-lived rock band Spinal Root Gang. Nowadays 270 Riverside is a pretty posh address on the Upper West Side. Last August, after the building went through a major renovation, neighbouring apartment 3C went for $4,073,000. But hey, this is now — 2017, and Madonna’s time was most certainly then — 1978.

The Lobby at 270 Riverside Drive — Circa 2017.

With its turn-of-the-century details, ornate lobby and river views, it’s hard to fathom that in 1978, 270 Riverside Drive was thought of as a ramshackle old building in a dicey neighborhood. The Upper West Side and Riverside Drive between 99th and 100th street was not prime real estate in the late 70’s. Still, it wasn’t as scary as the West 80’s, — now that was the rough stuff. In fact, the New York Times actually crowned West 84th street between Amsterdam and Columbus, as one of the two worst blocks in the city, and described it famously as a “gathering place of drunks, narcotics addicts, and sexual perverts.”

Today, things have improved considerably. With two of the city’s best sushi restaurants within 5 minutes of you, the best indie bookstore in the neighborhood (Book Culture) thriving on Columbus and 82nd St, and a slew of great Thai, Indian, and Italian resturants on Amsterdam and Columbus, life isn’t half bad here. You can still find rentals on this block too, but if you want a nice 1st floor 3 bedroom, be ready to spend $5k a month.

West 80’s in the Late 70's.

Madonna’s first real apartment was a fourth-floor walk-up at 232 East Fourth Street in “Alphabet City”/The East Village. The building sits between Avenue A and Avenue B, almost as far east as you can go in this part of Manhattan. Back in the late 70’s this was a no-mans land of drugs, punk rock, and street crime. It was what Madonna could afford back then.

After a renovation, the building’s address was changed to 230 East Fourth Street. Here’s a recent peek:

230 East 4th Street, Unassuming on the outside….

In Life With My Sister Madonna, her brother Christopher Ciccone described the 1978 East Village tenement flat as ‘”two small rooms, no furniture except a big white futon and a perpetually hissing radiator.”

“Madonna claims she existed during this hard time on popcorn, donuts, and yogurt, with forays into dumpsters for whatever she could scrounge,” writes Mary Cross in Madonna: A Biography. “Her father came to visit but was so upset by her living conditions — ‘a roach motel’ he called it — that he pleaded with her to come home”.

No Way THIS Chair Will Fit In THAT Apartment.

Today, the East Village and Alphabet City are probably the most desirable neighborhoods for young New Yorkers east of Brooklyn. The neighborhood boasts a collection of some of the best, and loudest, restaurants and bars in New York City, catering to anyone looking for a quitessential “downtown” New York night out.

And while 232 East 4th street is still a building tied to lower-income housing, this neighborhood is no longer affordable for any struggling artist or wannabee Pop Diva. In fact, even if you go further east, you won’t find a bargain. A recent penthouse sale at The Atles House, located at 325 East 4th street, between Avenues B and C, went for $2,295,759. You might think the sponsor seller would be happy with that number, but at -8% off “asking”, that price was likely kind of… borderline.

Special Bonus: Madonna Doesn’t Think Kevin Costner Is All That Neat:

Neat Mullet, Kevin.



Jack Isquith

NYC enthusiast. music fanatic. residential real estate sales. Harkov Lewis Team at Brown Harris Stevens. jisquith@bhsusa.com