Jackson Street Sky House: A Williamsburg Duplex with Two Private Roof Decks

Set within a boutique condominium on one of Williamsburg's quietest tree-lined blocks, this rare penthouse duplex delivers something few rentals can: two separate private roof decks, both already furnished and ready to enjoy from day one. One is a lounge-like retreat strung with string lights, furnished with a plush wicker sectional and coffee table; the other opens onto sweeping skyline views toward Manhattan, furnished with an outdoor dining table and chairs for entertaining. Move-in ready outdoor space like this is genuinely rare to find in Williamsburg.

The main level unfolds as a true loft, anchored by soaring ceilings, floor-to-ceiling windows, and rich wide-plank teak floors that run throughout. The open living and dining area leads to a Juliette balcony, while the well-appointed kitchen — quartz-style counters, stainless appliances, and a peninsula built for entertaining — anchors the space. A generously proportioned bedroom, full bath, deep closets, and an in-unit washer/dryer complete this floor, with central heat and air keeping the whole home comfortable year-round.

Upstairs, a private mezzanine level offers a second bedroom and a flexible office — ideal as a guest room, work-from-home setup, or den — bookended by those two furnished roof decks. It's a rare amount of separation and outdoor space for a Williamsburg rental, with room to spread out, host, or simply disappear for a while.

Jackson Street sits in the heart of Williamsburg's Graham Avenue corridor, near Mesa Coyoacan, The Meat Hook, and CTown Supermarket, with McCarren Park and the L train at Graham Avenue both close at hand.