It might be the most quietly iconic living room in American music history.
The year is 1965. Bob Dylan sits cross-legged on the floor in velvet. Behind him, his manager’s wife, Sally Grossman, reclines in a fire-red gown. Records and books are scattered around them — the casual clutter of counterculture. Daniel Kramer’s photograph became the cover of Bringing It All Back Home, and a shrine to the moment when folk cracked open into something stranger.
That same living room — and the estate it sits within — is now for sale for $4.9m in Woodstock, New York.
Credit: William Pitt Sotheby’s International Realty
Credit: William Pitt Sotheby’s International Realty
Credit: William Pitt Sotheby’s International Realty
Credit: William Pitt Sotheby’s International Realty
Credit: William Pitt Sotheby’s International Realty
Credit: William Pitt Sotheby’s International Realty
Credit: William Pitt Sotheby’s International Realty
Credit: William Pitt Sotheby’s International Realty
Credit: William Pitt Sotheby’s International Realty
Credit: William Pitt Sotheby’s International Realty
Credit: William Pitt Sotheby’s International Realty
Credit: William Pitt Sotheby’s International Realty
Credit: William Pitt Sotheby’s International Realty
Credit: William Pitt Sotheby’s International Realty
Credit: William Pitt Sotheby’s International Realty
Credit: William Pitt Sotheby’s International Realty
“A place for artists to do their work”
Set across 72 wooded acres, the estate offers the chance to own a piece of music history: a purpose-built creative compound and the nucleus of a cultural shift. It was designed, quite literally, for people who make things.
Albert Grossman, the formidable manager behind Dylan, Janis Joplin, and The Band, bought the property in the early 1960s and gradually expanded it into what became Bearsville. Grossman didn’t just want privacy — he envisioned a self-contained creative ecosystem: studios, salons, space to argue, drink, experiment. He called it ‘a place for artists to do their work.’ And it became one — a playground ground where folk, blues, rock, and poetry collided. Dylan, Joplin, and George Harrison made music here. Johnny Cash and, reportedly, Björk also spent time at the estate.
Dylan stayed extensively through late 1964 and early 1965, writing, reading, and shaping a voice that was becoming more surreal, political, and personal. While Bringing It All Back Home was recorded in New York City, many of its ideas and lyrics took shape in Woodstock, where Dylan encountered Beat writers, French symbolists, and the sounds that would fuel his electric turn.
That creative spirit still lingers inside the main four-bedroom bluestone house, built in 1914, with its wide-plank floors, brick hearths, and Arts & Crafts geometry. A four-bedroom guesthouse and rustic one-bed apartment round out the estate, alongside Viking Hall: a cathedral-beamed studio with sauna, soaking tub, and space to retreat or create.
The current owners, who bought the property in 2014, have preserved its patina while adding modern updates — including a heated saltwater pool, greenhouse gardens, and quiet system upgrades. It’s co-listed with Michelle Bergkamp and Kathryn Johnson of Corcoran Country Living, and William Pitt Sotheby’s International Realty.
