32 Old Route 199

Shepherd’s Knoll offers rare privacy and flexibility, which is less than two miles from the village. Set on four beautiful acres that include lawns, pastures, and lightly wooded areas, this distinctive property sits at the end of a long private drive.  It includes two spacious living units that could easily be converted back to a singlefamily home.

Unit One features four bedrooms, three bathrooms, and a finished lower level.
Unit Two offers two bedrooms and two bathrooms with a strong history as a shortterm rental.
Both spaces include woodburning fireplaces and a wood stove, creating a warm, inviting atmosphere.

Outdoor living shines here. expansive decks and porches overlook pastoral views, while the grounds include a charming studio cottage, a former sheep barn with storage, chicken coops, and established garden areas, ideal for creative use, light homesteading, or quiet retreat.

Located just minutes from Bard College, a campus that includes the Fisher Center, and Montgomery Place.

The property blends country seclusion with access to Hudson Valley cultural life.

Whether you need multigenerational flexibility, a home plus a guest setup, or a private sanctuary close to town, Shepherd’s Knoll offers a lifestyle that’s increasingly hard to find.