Built in 1789 for one of America’s first secret agents, the Spy Hill is now a private Estate situated in the heart of Hudson Valley — just an hour outside of New York City.

With a rich historical link back Enoch Crosby from the American Revolution, the Spy Hill Estate will intrigue both history and architecture enthusiasts.

Sitting on four acres overlooking the Middle Branch Reservoir in the southern Putnam County Town of Southeast. Amid its picturesque landscape of rolling hills sits the faithfully restored estate of Enoch Crosby, still retaining some of its old world charm.

While it’s classic Colonial shell still remains, the interior has been furnished with custom pieces and modern fixtures. The 3,000 square foot main house offers 3 bedrooms, 3 full baths, a library, and an outdoor stone veranda that leads to a 40-foot heated in-ground pool and spa.

The property also boasts a 19th-century barn that spans a spacious 3000 sq feet, housing a workshop, yoga studio, and greenhouse. A separate two-storey guest cottage also features various amenities such as an art studio and a custom kitchen, providing great hospitality.

It’s finished off with a white picket fence surrounding a landscaped and lit backyard, along with an impeccably manicured lawn that complements the picturesque Upstate setting.

Currently under Good Property Company, the Spy Hill Estate is offered for sale at US$1.625M. View this estate on its namesake website here.

Enoch Crosby — one of the America’s first intelligence agents

150 years before the emergence of CIA, Crosby was one of the country’s double agent, pretending to be a British spy while maintaining a cover as an itinerant cobbler and peddler. Tasked to infiltrate the Loyalists, not even his family knew he was working for America’s colonial cause. In fact, Crosby asked the Committee of Safety to promise to clear his name if he was ever killed in mission, and also received a special pass if he was captured by American forces.

Crosby’s was largely successful with his efforts. He roamed the Hudson Valley and upstate New York, where his accomodation and the now turned Spy Hill Estate lies. From Westchester County to Lake Champlain, Crosby infiltrated several Loyalist groups and returning with valuable information that contributed to the capture of many.

In 1821, James Fenimore Cooper published The Spy, a book that chronicles the exploits of a fictional character named Harvey Birch who takes after remarkable resemblance with Crosby. While there was never a confirmation, Cooper must have heard much tales from his neighbour John Jay, the first Chief Justice of the Supreme Court.