Originally dubbed Chateau de Montgomery by owner Janet Livingston Montgomery, this 434-acre bluff-top estate overlooking South Tivoli Bay was included by Andrew Jackson Downing in his influential taste-making book, Treatise on the Theory and Practice of Landscape Gardening of 1841. Acquiring the working farm in the early 1800s, Montgomery built a federal-style house at the terminus of a half mile-long deciduous allée. In the mid-1800s, architect Alexander Jackson Davis added classical revival exteriors to the Federal core, incorporating vistas of the Hudson River and Catskill Mountains. Other surviving Davis features include the classical coach house, a Gothic Revival farmhouse, and the Swiss Cottage.
Bequeathed to Montgomery’s youngest brother, Edward Livingston, Downing was consulted in the late 1840s on the layout of the gardens and the forest walks to the Saw Kill waterfalls. Livington’s son-in-law, Thomas Barton, began an arboretum in the 1840s, planning it with German landscape gardener Hans Jacob Ehlers. Coralie Livingston Barton designed the ornamental flower gardens. During the 1920s and 1930s, owner Violetta White Delafield terraced the western slopes, creating a series of garden rooms for roses, herbs, and perennials, and added the Wild Garden, a hedged ellipse, and the aquatic garden.
Montgomery Place was designated a National Historic Landmark in 1975. Delafield descendants conveyed title to Sleepy Hollow Restorations (now Historic Hudson Valley) in 1986; the estate opened to the public in 1988.