139 Watch Hill Road

A rare opportunity to own a stately mid-1800s center hall Colonial/Farmhouse estate set on over two picturesque acres. Offered for the first time in nearly fifty years, this timeless property is rich with history, character, and endless potential. A distinctive stone entry wall welcomes you, while a graceful circular driveway leads to a covered herringbone brick front porch. Inside, classic proportions and original period details create the perfect canvas for restoration and reimagination. The expansive kitchen, complete with a butler’s pantry and a separate room ideal for a future mudroom or laundry area (with basement access), flows seamlessly into a formal dining room with doors leading to a charming original flagstone patio. The patio connects to a screened porch overlooking the gardens—perfect for effortless indoor-outdoor living. A sun-filled living room with a wood-burning fireplace opens to a cozy den or office with a second fireplace, while an enclosed porch with slate flooring offers multiple access points and peaceful views of the sweeping grounds. Ideal for extended stays or multi-generational living, a private wing off the kitchen—featuring a sitting room, full bath, and additional room—can easily be transformed into guest quarters. Upstairs, the oversized primary ensuite offers a walk-in closet and an adjoining flexible space ideal for a home office, dressing room, or private retreat. A second ensuite bedroom with a cozy sitting area, along with two additional bedrooms connected by a Jack-and-Jill bath, provide ample accommodations for guests. The second floor features hardwood floors throughout. The grounds are truly special—an impressive corner lot with mature landscaping, stone walls, a tranquil stream, and a pool awaiting restoration or potential transformation into a unique water feature. A separate cottage, in need of full renovation, features a striking stone fireplace and offers incredible potential for a home office, studio, or guest house. Note lawn has been virtually enhanced. This is a once-in-a-generation offering for the discerning buyer seeking a historic estate to restore and make their own. Conveniently located just five minutes to the Cortlandt train station and under ten minutes to Croton-Harmon, both offering service to Grand Central in under an hour. Close to parks, Hudson River hiking trails, riverfront walks, Hudson National Golf Course, marinas, shops, and dining.