Beguiling Westchester Compound with Apple Orchard Has Questlove Connection

Imagine: it’s May, a sweet spring afternoon in the Northeast. Bright blue sky, a breeze like a soft kiss, sun shining, birds twittering, and the scent of flowers everywhere. You’re having friends over for an early supper. You decide to serve the meal in your apple orchard. Drifting apple blossoms cascade as you and your guests enjoy a glass of wine on your rustic table and benches, under twinkling lights.

Then of course, you drop a few names. “Of course in our guest house,” you murmur, “Questlove live-streamed at-home DJ sessions during the pandemic, for social distancing dance parties.”

A beautifully pruned apple orchard, complete with rustic table and benches, is but one attraction (alongside name-dropping of famous musicians) of this charming compound set on almost seven acres in Pound Ridge, one of the many peaceful country towns in New York’s Westchester County that reeks of money and prestige. About 50 miles outside Midtown Manhattan, it’s just north of Stamford, Conn, so perfect for anyone who works in that city center. The name “Pound Ridge” comes from the local Native Americans. They built an enclosure of saplings, and then drove deer and other game into the pound until they needed it for food.

Asking $3.95 million, the gated compound, owned by a couple of life coaches, consists of two houses plus a swimming pool. It’s repped by Caroline Shepherd at Houlihan Lawrence.

The vintage main house manages to be stately yet incredibly homey. The front porch is perfect for relaxing while enjoying the scenery, although the rest of the property includes many other inviting patios and seating areas. Both the living room and the sunny yellow-painted kitchen include fireplaces. glossy oak floorboards, and tall windows that frame bucolic views. There are charming built-ins throughout the house, including the bedrooms.

Currently housing a gym and a home office, the second residence also has a complete kitchen that makes it perfect for parties and/or extended stays of family and friends and/or renting to Roots front-men. The guest cottage’s showplace is, however, the barn-timbered great room with its huge fieldstone fireplace, wide-plank floors and mullioned windows.

If nearly seven acres isn’t enough room to roam, the compound is quite close to a 4,315-acre park, with hiking, fishing, horse-back riding and even cross country skiing. Truly the best of all worlds, especially when you crack open a bottle of last year’s cider for your guests.