Presenting Canoe Hill, a remarkable 63-acre estate and vineyard in the heart of Millbrook, New York. This extraordinary property stands as a testament to architectural evolution, where a storied mid-1700s colonial core has been thoughtfully expanded to create a remarkable 12,650 SF main residence that seamlessly marries Colonial, Georgian and Greek Revival influences. Two significant expansions, designed by renowned architect Jimmy Crisp, create a magnificent home around the original core and seamlessly introduce contemporary luxury without compromising the home's historic integrity. Canoe Hill is approached through a gated entry and winding half-mile private drive through established vineyard rows and majestic trees. The rolling landscape presents a tapestry of meticulously maintained formal gardens, productive vegetable plots, heritage fruit trees, and pristine spring-fed ponds—creating an environment of pastoral perfection and offering unparalleled privacy and natural splendor. Entered through a gracious foyer with a dramatic curved staircase and double-height ceiling, the center corridor leads you through the heart of the historic part of home into an expansive family wing featuring an immense chef's kitchen with dining area and stone fireplace. The adjacent family room is highlighted by vaulted ceilings, original beams and a stone fireplace. Upstairs are five thoughtfully appointed bedrooms, including a palatial primary suite featuring a fireplace and dressing room, plus two en-suite bedrooms, one with fireplace. Two additional bedrooms on the third floor share a full bath. The finished basement reveals a professional wine cellar with tasting rooms, a children's playroom, laundry and abundant storage. The West Wing presents entertaining at its finest, featuring a 12-seat dining room, a sun-drenched morning room, and a spectacular formal living room with 22-foot ceilings, a stone fireplace and private veranda with an additional outdoor fireplace. The East Wing is the latest expansion and includes a library also serving as a second dining room and an office suite. The crown jewel of this wing is the remarkable Tartan House, accessed through a doorway concealed by a Tartan painting — an entertainer's paradise featuring a grand Tartan gathering room with full bar, billiards and stone fireplace, complemented by two distinct Tartan bedroom suites above, and below, a glamourous, tiered 12-seat movie theater that indulges the senses and is an entertainer's showpiece. The outdoor amenities rival the finest resort destination and feature a fully landscaped pool area enhanced by two covered pergolas - one housing a complete outdoor kitchen with pizza oven, while the adjacent boasts a full bar for seamless entertaining. Other exterior features include a sculptured rose garden entertaining area, walking trails, a golf hole and gorgeous six spring-fed ponds that keep the grounds lush and vineyard irrigated. The standalone guest house presents a private retreat with generous living spaces with terrace, a full kitchen, a bedroom suite and additional full bathroom and pantry. A professionally equipped gymnasium and three-car garage complete this impressive structure. At the heart of this exceptional compound lies Elysabeth Vineyards, a fully operational boutique winery and bottling facility offering, high-quality wines produced from estate grapes. Varietals include Cabernet Sauvignon, Pinot Noir, Cab Franc, Merlot, Chardonnay, Reisling and Gewürztraminer. Current production is 600+ cases annually. The winery includes a turnkey 2,700 SF residence complete with a private tasting room, terrace and catering kitchen offering both commercial potential and intimate entertaining possibilities for the discerning oenophile. Canoe Hill represents a unique opportunity to own a piece of Hudson Valley history while enjoying the finest contemporary amenities and endless possibilities. This is a Co-Listing with The Corcoran Group.