Character, charm, and exceptional flexibility come together in this one-of-a-kind Middlebury home. Offering far more space than meets the eye, this property blends timeless craftsmanship with a versatile layout designed to fit today's evolving lifestyle. The main home features expansive living and dining spaces, a full bath, a main-level bedroom, and an additional flexible-use room ideal for a home office, den, guest space, or hobby room. Upstairs, you'll find two generously sized bedrooms with abundant closet space and a convenient half bath. A standout feature is the potential in-law setup, complete with its own living area, bedroom, and full bath, providing endless possibilities for multi-generational living, extended guests, or added privacy. Throughout the home, you'll appreciate the details that make this property truly special-from beautiful built-ins and custom trim work to the character and craftsmanship rarely found today. Outside, enjoy a spacious backyard designed for both relaxation and entertaining, featuring a large above-ground pool with surrounding deck space, perfect for summer gatherings and enjoying the outdoors. The lower level offers additional storage, garage space, and a workshop area complete with a workbench, ideal for hobbyists, craftsmen, or anyone in need of extra room. This is not your average Cape-style home. With its generous living space, unique layout, and endless possibilities, this home it ready for its next chapter!