A rare opportunity to own TWO single-family adjacent homes in the heart of East Hampton! Rich in history and thoughtfully updated, the main residence at 124 Main Street beautifully blends timeless architectural character with the comfort and convenience of modern living. Historic details, classic craftsmanship, and tasteful updates create a home that is both elegant and inviting. A first-floor bedroom and full bath provide the option for a desirable primary bedroom suite or flexible living arrangement to accommodate a variety of lifestyles. Situated toward the rear of the property, 126 Main Street is a second single-family residence offering exceptional versatility. While it could benefit from some updating, it presents endless possibilities as an in-law home, income-producing rental, private guest house, home office, studio, or space for entertaining family and friends. Whether you're looking for multi-generational living, rental income, or simply the flexibility of owning two homes on one parcel, this unique property offers endless potential in a desirable location close to East Hampton's charming downtown, Lake Pocotopaug, restaurants, shopping, and local amenities. A truly one-of-a-kind opportunity!