What We Love

  • “Just right” size living space: main floor living, separate guest space in the house, and separate guest house/office building. Cozy, comfortable for two and expandable for children and visitors
  • The spectacular view that changes every hour in every season, always awe-inspiring
  • Quiet and privacy, accessible to everything available in a large city, from cultural to recreational to medical
  • Running businesses and communicating around the world surrounded by beauty either from the house or studio
  • South Woodstock’s warm, interesting community and respect for privacy — community when you want it, isolation when you don’t

Matching a sophisticated sensibility with a spectacular pastoral site at a height of land with panoramic views from Mt. Ascutney to Mt. Washington, High Riding’s 75.5 acres comprise one of the most beautiful land parcels in Woodstock and includes two separate residences along with two garages and a stable.

Architect Harvey Stevenson’s (NYC Mayor Fiorello LaGuardia’s “chief architect”) 1962 modern design at 99 Darling Road embraces the striking layered views of meadow, near hillsides, and distant mountains. The 2,365-square-foot interior blends Japanese-style simplicity with Vermont provenance, such as curved walls of a honey-colored butternut veneer, curly maple on the stairs, and birds-eye maple on the kitchen cabinets. The large main level master bedroom is paired with two additional bedrooms on the garden level, which opens to a covered patio. A detached two-car garage is conveniently accessible from 99.

The “Studio” at 97 Darling Road, a 2,384-square-foot separate building, has a 2-bay garage, 3 offices (or living) areas on the first level accessing a stone patio, and a completely equipped two-bedroom guest apartment above with lovely North light and near and long-range views. A private deck leads down to the stone patio.

The landscape combines birch and maple glades with mature specimen trees of many varieties in a park-like setting, naturalistic plantings, perennial gardens and dramatic stone steps leading down to a spring, stream and sky-fed swimming pond. High on the ridge are over 800 sugar maples, which are tapped for maple syrup. Around the property are apple trees, well maintained pastures, forest, private riding and hiking trails and a three-stall stable. High Riding is in the heart of horse country and surrounded by quiet dirt roads, trails and is 2.4 miles to GMHA. Nearby is skiing, golf, biking, hiking, fishing and gold panning.

The total tranquility, serenity and privacy are rare so close to civilization: easy access to the South Woodstock hamlet and Woodstock village. There is an excellent local health center and the world-class Dartmouth Hitchcock Medical Center in Hanover. 24 miles from Lebanon Airport, NH; 95 miles from Burlington, VT and 105 miles Manchester, NH. High quality scheduled bus service to Boston airport from W. Lebanon via Dartmouth Coach, complete with internet.

Property Details


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