Set on a quiet dead-end street in the heart of Shaftsbury Village, this 1948 Cape offers classic character, a flexible floor plan, two detached garages, and an exceptionally large 1.65-acre double lot. Inside, gorgeous hardwood floors run through much of the home and warm wood-paneled spaces add to its vintage Vermont appeal. The first floor offers a bright kitchen with new appliances and lighting, dining room, spacious living room, dedicated office, bedroom with built-in shelving and laundry hookups, and a half bath. Upstairs are two generously sized bedrooms, a full bath, and additional closet space. Original details remain, including solid wood doors with glass knobs, while newer vinyl replacement windows and vinyl siding add practical updates. Outside is where this property really sets itself apart. The expansive double lot provides an unusual amount of land for a village setting, with potential for future subdivision subject to municipal/state approvals. Two separate garages offer tremendous versatility for vehicles, storage, hobbies, or workshop space. The garage finished to match the house can accommodate approximately 2-3 vehicles in tandem and features power, insulation, an automatic opener, and pull-down stairs to overhead storage. The larger brown garage provides another vehicle bay plus heat, electricity, a utility half bath with urinal, and an expansive second-floor workshop. An elevator/lift also connects the garage levels; functionality has not been verified. All of this is tucked into an established neighborhood where you can enjoy the convenience of village living without sacrificing elbow room. Walk to the elementary school, playgrounds, Town Offices and Post Office, or head out for a stroll along the sidewalk loop around Cleveland Avenue. With 1.65 acres, three bedrooms, two garages, abundant workshop and storage space, and a peaceful location, 81 Holliday Drive offers a combination that is increasingly hard to find in Southern Vermont.