This 10-Acre Farmhouse Estate Offers Charm in Chester

Listed on the market for $1.25 million, this Orange County farmhouse estate has three structures, rolling hills, and a panoramic backdrop.

In the Orange County enclave of Chester, preserved land and a forest surround this 10-acre farmhouse estate. Listed by Ellis Sotheby’s International Realty, the property is on the market for $1.25 million in the lower Hudson Valley town. The 1900s estate, known as Woodside, is located at 282 Laroe Road and consists of three structures, an inground swimming pool, and a picturesque backdrop of Sugar Loaf Mountain.

The property’s structures include a 6,600-sq-ft, six-bedroom, four-bath colonial farmhouse, an 8,000-sq-ft red barn with a five-bay garage, and a post-and-steel building previously used as a hunting lodge.


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Many of the home’s features display 19th- and 20th-century details, including hardwood floors in the front and parlor rooms, vaulted and beamed wood ceilings, walls of windows, a contemporary circa 1960s addition, and two fireplaces that punctuate the living room and recreation room on the first and second levels. Along with its structures, the property also includes an inground swimming pool, pool shed, and dressing room.

Woodside is co-listed by Jacob P. Matthews and Jody Atkinson of Nyack-based Ellis Sotheby’s International Realty, who described the property as a “legacy property for the ages,” adding “Woodside is one of the most inspiring real estate offerings to come to market in recent times. It is well-suited for entertaining guests and connecting with nature, given its abundant indoor and outdoor spaces and amenities.”

Not only does the farmhouse estate have a view of Sugar Loaf from the backyard, but the 10-acre property has been carved out of a 320-acre purchase by the Orange County Land Trust to facilitate the protection of the neighboring mountain and its surrounding undeveloped acreage. The purchase was heralded as one of the largest land preservation projects executed in the region.

According to Jim Delaune, Orange County Land Trust executive director, the Land Trust intends to preserve the remaining 310 acres of land and provide first-ever public access up the mountainside and a future trail system connecting Sugar Loaf Mountain to Goosepond Mountain State Park, a 1,700-acre park in Orange County operated by the Palisades Interstate Park Commission.

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Central to the hamlets and villages of Sugar Loaf, Monroe, and Warwick, Woodside is in a prime location for access to orchards, vineyards, Sugar Loaf Performing Arts Center, Legoland, Woodbury Common Outlets, Goshen Historic Track, and the U.S. Military Academy at West Point.

Woodside is located at 282 Laroe Road in Chester.

Related: 2 Red Hook Homes on the Market for Under $900,000

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