Overlook Drive

Hillsdale, NY 12529

Situated in Hillsdale, this extraordinary 150-acre hilltop offers an opportunity to create a private or legacy estate. Rising to over 1,300 feet, the parcel provides for sweeping panoramic views of the Berkshires, Taconic Range, and Catskill Mountains. Established logging roads and trails wind through the landscape past historic stone walls, dramatic rock outcroppings, seasonal streams and waterfalls. Combined with the varied topography, these features lend an air of serenity and seclusion. The property is currently enrolled in a forestry program that affords property tax reductions and opportunities for periodic timber revenue. Two distinct building envelopes, each encompassing three to four acres, are excluded from the program, allowing for immediate development while preserving the tax benefits. For those seeking broader vision, the acreage also presents the potential for subdivision, presenting a unique investment opportunity with far-reaching views in a highly desirable region. Ideally positioned at the crossroads of the Hudson Valley and the Berkshires, this exceptional offering combines privacy and natural beauty with access to renowned cultural institutions, fine dining, and year-round outdoor pursuits.

Listing courtesy of Rouse + Co Real Estate LLC matt@rouseco.com


Based on information submitted to the MLS GRID as of 2026-04-19 06:29 AM EDT. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.