The Woolley House, located at 587 Route 121 East and built around 1818, is a rare and remarkably preserved 2.5 story brick residence in the Federal style. This home, originally constructed for early woolen mill owner John Woolley, features a side-hall layout, blind-arch entryway, and fanlight transom. Original details are beautifully preserved throughout, including four elegant Regency fireplaces, an original central cooking hearth with an iron crane and 2 concealed baking ovens, wide pine floorboards, classic 12-over-12 windows, and a charming hand-crank doorbell that evokes its historic past. A tasteful modern addition expands the living space with a custom marble kitchen, a formal dining room, and three private office suites with outdoor access ideal for remote work or creative pursuits. Upstairs, the home features four comfortable bedrooms, two updated bathrooms, a lounge and a finished loft with a cozy library retreat. Outside, the home is surrounded by mature perennial gardens and one of Windham County's most admired curated Hosta collections, offering a peaceful oasis in every season. With its architectural significance, modern functionality, and ample space to live, work, and explore, the Woolley House is a truly timeless property in the heart of historic Grafton. The property is part of the Mechanicsville Historic District in Grafton, Vermont. A well-preserved 19th-century hamlet recognized for its architectural, community planning, and industrial significance. The district includes 10 contributing historic homes, all built before 1860, and this designation places the Woolley House on the National Register of Historic Places.