A rare offering in sought-after Upper Grandview, this distinctive property brings together a beautifully restored Dutch Colonial with origins believed to date to the mid-1800s, a turnkey one-bedroom cottage, and nearly two private acres overlooking the Hudson River. Evolved and expanded over generations, the main residence reflects the character of an earlier Hudson Valley home alongside its circa-1920 architectural identity. Two separate residences offer exceptional flexibility for extended family, guests, a private home office, or additional living space. Thoughtfully restored with careful attention to its historic character, the main residence features beautifully refinished original wood floors, preserved period details, abundant natural light, and Hudson River views from many rooms, with more expansive vistas as the leaves fall. At the heart of the home is a striking new designer kitchen with custom cabinetry, Carrara marble countertops, premium appliances, and a built-in dining banquette. An elegant living room with fireplace opens to a sun-filled enclosed porch, where walls of windows frame views toward the river. Upstairs, the primary bedroom opens to a private balcony with seasonal Hudson views and enjoys direct access to a beautifully tiled bath. A versatile room currently used as a dressing room can also serve as a nursery, home office, or additional bedroom. Two additional bedrooms and a second tiled bath complete the level. The walk-out lower level offers a fifth bedroom or den, full bath, mudroom, and laundry area, with direct access to the outdoors. Set apart from the main residence, the fully renovated one-bedroom cottage has a character all its own, with a modern kitchen, open living and dining space, full bath, private laundry, patio, and seasonal river views. Nearly two acres of open lawn and mature trees surround the two residences, creating a private country setting with glimpses of the Hudson throughout the landscape. Just minutes from Nyack and Piermont, with their restaurants, cafes, galleries, parks, marinas, and farmers markets,and within easy reach of New York City. This property offers an increasingly rare combination: two residences, meaningful acreage, Hudson River views, historic character, and remarkable privacy.