Tucked at the end of a private, town-maintained road at the base of Red Mountain, this exceptional property offers privacy and flexibility: two fully independent residences, beautiful grounds and a peaceful setting just minutes from the heart of Arlington and an easy drive to Manchester. Surrounded by gardens, orchards, terraces, and forest, this is a true Vermont retreat. The 2,676-square-foot main residence is warm, light-filled, and thoughtfully designed. River-reclaimed heart pine floors, new Andersen windows, a wood-burning fireplace, and screened porches add character throughout. The main level offers a living room, kitchen and dining area, laundry and walk-in pantry, powder room, library/office, and primary suite with French doors to the rear patio. Upstairs are two bedrooms plus a flexible fourth room ideal for an office or nursery. A walk-in attic offers additional potential. Just steps away, the 1,152-square-foot guest house is a substantial second residence with a dramatic great room, cast-iron wood stove, charming kitchen, bedroom, full bath, laundry, and loft. Ideal for extended family, guests, caretaker, home office, or potential rental income. Both have a dry basement for storage and attached two-car garages. Mechanical systems are impeccably maintained, including hot air heat, central air, and whole-house generators. Outside, approximately five cleared acres feature orchards, gardens, lush landscaping, a deck, stone terraces, and an architecturally designed fire pit. Beyond the homes, the property extends across approximately 125 acres with trails, a private stream, and Battenkill River frontage. 121 acres are enrolled in Vermont's Current Use program, providing meaningful tax savings. A natural spring serving as one of the town's water sources also provides water to the property at no cost. Private, versatile, and remarkably well cared for, this is a rare opportunity to own two complete residences in an extraordinary Southern Vermont setting.