There are homes with history, and then there are homes that invite you to become part of it. Originally rooted in the Joseph Hollister II homestead, this c1740 property blends early American character with modern updates, creating a setting that feels both timeless & completely livable. Set along scenic Tryon Street, the home captures beautiful light from sunrise to sunset, with views that reflect the surrounding farmland and river landscape. Inside, the kitchen opens effortlessly to a welcoming family room, where wide board pine floors & exposed beams create warmth & style. Dining area, anchored by a fireplace & original beehive oven, sets the stage for gatherings both intimate & grand. Throughout the remainder of the home, preserved chestnut floors add rich texture & authenticity. With 3 fireplaces in total, each space carries its own sense of comfort & purpose, from the living room to additional flexible rooms ready to suit your needs. Upstairs offers a spacious primary suite w/vaulted ceilings, along w/3 additional bedrooms, each w/character & functionality. An incredible barn provides exceptional versatility, including a 2 car garage w/high ceiling, a 3rd bay, dining/entertaining area with barn doors open to bucolic views & expansive upper level space ideal for rec, work, or guests. Equally important, the home is supported by modern essentials including public water, public sewer, and natural gas. New Roof 3/2026 & Buderus boiler serves the home efficiently. Scroll down! There are many ways to begin the story of this home. One could start in 1740 with the Joseph Hollister II house, tracing its roots through centuries of settlement, families, and the quiet unfolding of South Glastonbury's history, speaking of lineage, architecture, and provenance, but that would be predictable, and there is nothing predictable about this home. Instead, turn the page. This is not simply a historic property, but a home that lives with a certain rhythm and mood, where old meets new in a way that feels entirely natural, a place that has been admired, gathered in, and lived in deeply for generations, truly iconic. Set along scenic Tryon Street in a highly coveted location, the setting tells its own story, with sunsets stretching across the river to the west and quiet mornings over farmland to the east, where walks to Hops on the Hill or the ferry become part of daily life, neighbors wave, horses graze, and the rhythm of the land carries on. Inside, the home feels both expansive and intimate, with a kitchen that anchors the first floor and connects seamlessly to an addition, opening to a warm family room with exposed beams and a sweeping dining area with a grand fireplace and original beehive oven. Wide board chestnut floors add rich texture throughout the original section and pine board in family room addition, while a formal living room and additional spaces offer flexibility for quiet moments, music, or a private office. Upstairs, the primary suite features vaulted ceilings, a generous walk in closet, and a well appointed bath, with three additional bedrooms that carry forward the home's character. The barn stands as its own experience, offering soaring ceilings, space for multiple vehicles, and above it a striking gathering room with barn doors and a long wooden table, perfect for farm to table dinners and celebrations, while a full loft above provides endless flexibility with an additional bedroom and private en suite. The grounds offer a level backyard with beautiful, ever changing views, and the home is supported by modern essentials including public water, public sewer, and natural gas, along with a Buderus boiler, a newer basement, and a recently installed roof. Thoughtfully preserved and carefully updated, this is a home ready for its next chapter, waiting for someone new to turn the page.