The Sing Sing Gated Community… Our Residents Just Can’t Leave! 

If you’re like me and you love waterfront property, privacy, terrific security and and homeowners association that doesn’t admit just anybody, the Sing Sing Gated Community might just be for you. 

Nestled on the banks of the scenic Hudson River in downtown Ossining, New York-my hometown- the Sing Sing gated community occupies 130 acres of prime riverfront real estate just a stone’s throw from the Metro-North train station. A mere 30 miles from Grand Central, Sing Sing is “up the river” as they say from Gotham, a short ride on the Metro North Hudson line. Of course, it takes more than a train ride to get in.  

Sing Sing is one of the oldest gated communities in New York (and the USA) and was actually built by the original residents! The Homeowner association president is actually known as the “warden” which gives the HOA a quaint charm. Among the amenities, the “longest mile” was originated here and is a popular feature in similar gated communites in Texas. 

While not a co op, residency at the Sing Sing Gated community does require board approval. There is also a minimum down payment rule, which actually tends to vary with the credentials of the applicant. Some characterize the down payment as an arm and a leg, others dismiss it as highway robbery. Despite the unique standards, there are seldom any vacancies. 

Actually, when I was a kid I remember the lights flickering in our neighborhood briefly and then there would be a vacancy the next morning, but that was a long time ago and the details are sketchy. Unlike a co op where residents get a proprietary lease and condos, where you get a deed, residents of sing sing are issued a “sentence” which I am sure dates back to New York’s old dutch roots. 

Security is what any gated community offers, and the Sing Sing Gated Community really excels in this area. They pride themselves on having 24 hour doormen- 1700 of them actually- friendly security, numerous towers with additional concierge staff to help residents find things like lost contact lenses, chipped teeth and the like, and they even have a physician and clinic right on the premises! Not only that, the Sing Sing Gated Community is an “all inclusive” place, with 3 meals a day served 365 days a year. They also have a library, a ball field, and “old school” physical fitness offerings, such as group calisthenics, “balls and chains” and even throwback marble and mallets! 

The concierge staff, especially the ones in the towers, are very protective of their residents’ privacy. As a matter of fact, when I took some of these pictures, one of them yelled at me and threatened to stuff my camera somewhere painful, and all I could think of was what a swell guy he was for protecting his people’s privacy like that. I’ll bet the residents really love that guy. 

Like many exclusive neighborhoods, the Sing Sing Gated Community has had many famous residents: David “son of Sam” Berkowitz, Julius and Ethel Rosenberg, and Lucky Luciano. The community is very selective about who gets residency here, and none of the openings are on the MLS. So, if you’d like more information about how to become a resident at Sing Sing, send me an email or call your local parole officer. 

Next week: 

Want an island getaway? Why not Rikers? 

Related posts:

“The Sing Sing Triathalon: Dig, run, swim.”

Happy April 1st!