Set on the north side of the Dorset Green, 86 and 78 Church Street present a rare village compound in the heart of Dorset. Fully renovated with exceptional attention to detail, this refined micro-estate blends timeless New England character with sophisticated modern living. Encompassing the main residence, guest cottage, gardens, and garage, the property is both gracious in scale and intimate in feel, the quintessential “new old house” imagined to perfection. Beautifully proportioned rooms are filled with warmth and elegance. The chef's kitchen features a walk-in pantry with prep sink and dishwasher, plus a dedicated coffee station and refrigerated drawers. The living room opens to a covered porch overlooking the Green, while the screened porch with a stone fireplace connects seamlessly to the dining room, deck, and patio for effortless indoor-outdoor living. A library hallway leads to a bright laundry room and stunning powder room. The billiards room and den offer richly layered finishes and a more intimate atmosphere. Original beams, remarkable millwork, wide-plank pine floors, two staircases, and generous hallways and landings create an effortless sense of flow throughout. The main residence includes two private primary suites, three additional guest bedrooms, marble baths, and beautifully curated gathering spaces. Outside, mature gardens, stone walls, a water feature, fire pit, and outdoor entertaining areas create a secluded retreat. A separate gym, spa, or hobby space opens directly to a tranquil zen garden. The charming three-bedroom guest cottage, complete with its own screened porch, offers ideal accommodations for guests or potential rental income. A singular offering where historic Dorset charm meets elevated village living on one of Southern Vermont's most iconic addresses.