This Connecticut Country Estate Looks to Surpass Local Sales Record for a Second Time

When a secluded country estate in Connecticut’s historic Litchfield County sold in 2004 for $4.75 million, it marked the highest amount ever paid for a home in the tiny town of Roxbury, a bucolic and affluent area about 60 miles outside of Manhattan that’s long been a favorite getaway among media and entertainment industry movers and shakers. Marilyn Monroe and Arthur Miller, Gay Talese, William Styron, Stephen Sondheim, Frank McCourt, Dustin Hoffman, Graydon Carter, and Candace Bushnell have all at one time or another lived in the rolling hills around Roxbury.

The current owners of the estate, who added about ten acres to the now more than 20-acre property, have now listed the property for $6.5 million, which would once again establish a new local sales record. The current record for Roxbury, based on available data, stands at $5.54 million, a bar set in 2021.

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11 Raven Rock Roxbury Connecticut
The main house is complemented by a two-bedroom guest cottage and a one-bedroom staff apartment.

The rambling residence was custom built in the early 1990s for Joseph and Hilary Califano; she’s the late daughter of late CBS founder and chairman Bill Paley, and he’s a distinguished attorney and professor who served as a White House Domestic Affairs Advisor to Lyndon B. Johnson in the 1960s and as the U.S. Secretary of Health, Education, and Welfare during the Carter administration in the late 1970s.

In addition to the main house, with four bedrooms and five and a half baths in about 5,600 square feet, the expansive estate offers a 1,500-square-foot, two-bedroom, two-bath guest cottage, plus a one-bed, one-bath caretaker’s apartment above the three-car garage.

11 Raven Rock Roxbury Connecticut
The view from the main house encompasses the rolling hills of Litchfield County.

The main house offers elegantly proportioned public rooms with high ceilings and expansive millwork, a total of four fireplaces, and mullioned windows and French doors that frame serene views. Flanking the double-height foyer are a fireside living that spills out to a stone-floored sun porch and a formal dining room, while the more relaxed and cozy great room offers a gourmet kitchen with minty green cabinets, a casual dining space, and a stone fireplace between built-in bookshelves. Just outside the great room is an elevated deck for dining and relaxing with a long view over the property toward the Steep Rock Preserve in the neighboring town of Washington.

The home, squirreled privately at the end of a long, winding drive, is situated amid mature gardens and vast, emerald carpets of rolling lawns bordered by dense woodlands. There’s a tennis court to work up a lather and a blue stone-trimmed swimming pool situated below the house to cool off. And, for those who value seclusion, there’s not another home within sight.

The property is available with Rick Distel and Susan Vanech of Compass.

Click here for more photos of 11 Raven Rock Road.

11 Raven Rock Roxbury Connecticut
11 Raven Rock Roxbury Connecticut

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