Historic House Listings

Sold. Owned by Charlie Chaplin descendants. Highlands Hobbit House in New York. $338,000

November 11, 2023

This is such a unique house! It is owned by the descendants of Charlie Chaplin. The Highlands Hobbit House was built in 1923. It is located on 1.80 acres in Fort Montgomery, New York. The home features a stone wood burning fireplace, exposed beams, hardwood floors and beautiful wood doors. The home is situated in the Hudson Valley and not far from Bear Mountain State Park. Three bedrooms, two bathrooms and 1,238 square feet. $338,000

Contact Deborah Waters with Howard Hanna Rand Realty: 845-674-7552

From the Zillow listing:


Whether used as a weekend retreat, investment rental, or full-time home, the Highlands Hobbit House in the Hill, owned by descendants of Charlie Chaplin, is truly one of a kind. Imagine waking up each morning to the breathtaking, rolling hills of the Hudson Valley. Picture yourself nestled in the treetops, basking in the warm glow of the evening sun, as you gaze out onto ships sailing under the Bear Mountain Bridge across the majestic Hudson River. The architecture of this home is a blend of organic shapes and natural materials which helps it blend into the hillside. The orientation maximizes privacy while also taking advantage of the scenic views. The cozy and inviting inside, including the two-level, stone wood-burning fireplace, double-staircase, and loft, make it feel like a true retreat from the outside world. The possibilities on how to use or renovate this almost two acre property on a private road next to the Black Bear Ranch, are only limited by your imagination. The Highlands Hobbit House in the Hill is a work of art appreciated by the discerning eye. 15 minute drive to multiple train stations; 5 minutes from Bear Mountain State Park and numerous hiking trails; 8 minute drive to the gates of West Point.



Let them know you saw it on Old House Life!