The Hudson Valley has attracted New York City’s elite since the Gilded Age, offering up large and luxurious retreats amid breathtaking natural beauty. It remains a hotbed of luxury real estate, with an ever-growing number of expansive retreats tempting affluent city dwellers. In September, the Sears family’s sprawling 106-acre estate listed for $6 million. Now, a spread more than double that size (and price) has hit the market for $14.5 million. Michael Stassi and Jeb Hart hold the listing.

Known as Deep Acres, the secluded compound stretches out over 293 acres in Kinderhook, New York, making it one-third as big as Central Park. Offering unobstructed views of the Catskills, the property comprises six separate parcels, which are anchored by a Greek Revival manor of 4,900 square feet, a two-story cottage, a swimming pool, and a renovated barn.

The main home dates back to 1858, but don’t let that deter you: The 19th-century abode has been thoughtfully modernized for 21st-century buyers, with four bedrooms and five full baths making it perfect for large families.

The foyer acts as an elegant starting point, with a breakfast room on one side and a Mahogany-paneled library on the other. Further in, the living room is decked out with Douglas Fir flooring, sage green walls, and a wood-burning fireplace. Nearby, the chandelier-lit dining room seats up to 10 guests beside buttery yellow walls and French doors that unfurl to a covered porch with sweeping meadow and mountain vistas. Elsewhere on the main level, the sleek chef’s kitchen is equipped with a stainless-steel gas range, a Sub-Zero fridge, and a center island for prep.

A grand staircase and elevator connect all levels. The second floor is home to the charming primary, three guest bedrooms, and an office, while the third floor is dedicated to a studio. Back downstairs, the lower level is outfitted with a gym, a sauna, a second pantry, a laundry room, and a cedar walk-in storage closet.

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Heading outside, trimmed hedges and manicured gardens frame a long, rectangular swimming pool. The yard sports a timber-framed barn with a changing room for swimmers and a garden room for green thumbs. The grounds also feature a “head house” garden complex and glass conservatory imported from England, a nearly 3,000-square-foot guest house with three beds and two-and-a-half baths, and a heated three-car garage with a second-floor office apartment. Plenty of space for wealthy New Yorkers, then.

Click here for more photos of the Kinderhook property.