A rare village offering on one of Millbrook's prettiest streets, this beautifully updated three-story Victorian blends timeless character with thoughtful modern upgrades, along with the added benefit of a separate carriage house. The main residence features five bedrooms and three bathrooms across three spacious light-filled levels, with hardwood floors throughout and classic architectural details that reflect the home's historic roots. The welcoming living room is anchored by a cozy wood stove, creating a warm gathering space, while mini-split air conditioning systems provide efficient year-round comfort. A mudroom entry adds everyday practicality, perfect for village living. Outside, a large stone front porch with its inviting swing offers a welcoming place for morning coffee or evening unwinding. The fenced yard with mature landscaping offers privacy and space to entertain or garden, complemented by a stone-walled patio just off the dining area. Adding exceptional flexibility and value, the property also includes a separate two-bedroom, one-and-a-half-bath carriage house with vaulted coffered ceilings and charming loft spaces, offering wonderful possibilities for extended family, guests, an office, or potential rental income. The property also offers a small artist's studio with a full bathroom. With dedicated parking for up to six cars and an unbeatable location just moments from the heart of the Village of Millbrook and its shops, restaurants, library, tennis courts and more, this home offers the best of village living in one of the Hudson Valley's most sought-after communities. Classic Victorian charm, modern comfort, and a coveted steps-to-village location; this is truly a special Millbrook opportunity.