Step into a piece of Hudson Valley history reimagined for a modern lifestyle. This stunning 1865 village colonial offers the perfect synergy of historic charm and contemporary utility, situated on nearly an acre of private, level, professionally landscaped, and wooded grounds in the heart of Pine Plains. The Main Residence: The primary home features the hallmark elegance of the 19th century--original moldings, wide-plank wood floors, built-ins, period beadboard, handrails, and balusters, and a signature yellow front door--paired with modern updates including a sun-drenched, eat-in gourmet kitchen with cast concrete countertops, premium appliances, and a midcentury wood-burning fireplace, all overlooking the private yard with its bluestone patio and walkways. Downstairs, there is a gracious front parlor and dining room with an adjacent butler's pantry and 1/2 bath, while upstairs there are 3 bedrooms and a full bath with a double vanity. The freshly renovated attached one-bedroom, one-bath apartment with a butcher block kitchenette and its own covered porch with a separate entrance adds exceptional value. Whether used as a guest wing, a rental to derive income, or a private suite for extended family, this secondary space provides flexibility rarely found in village properties. The Carriage House: 1,705 sq. ft. A truly unique, soaring studio/workshop/gallery complex with skylights and industrial finishes--an ideal studio space for a professional maker or a grand-scale home office, heated for year-round use. Recent structural and utility upgrades include an extension with new thermally insulated windows, insulation, and lighting. The Garden & Patio: Truly a gem for the avid gardener, this property is regarded as one of the nicest private gardens within the village of Pine Plains, featuring thoughtfully chosen, established perennials throughout; a beautiful kitchen garden off the deck; mature trumpet vines and wisteria providing privacy on the bluestone patio; several flowering fruit trees including apple and pear trees that bear fruit; and a circular garden feature in the yard centered on a beautiful Japanese maple tree that puts on a show every fall. A grove of tall trees surrounds the east side of the property for privacy and shade in the summertime. Two outbuildings provide plenty of storage for garden tools and supplies. Leave the car in the gravel drive as you are steps from Pine Plains village favorites including Stissing House and Champêtere restaurants and a short bike ride away from the Stissing Lake recreational area and Stissing Mountain hiking trails with the best of northern Dutchess, Columbia, Litchfield and Berkshire counties within easy reach. 2 hour + drive from NYC to this enchanted village compound.