Built in 1900, this beautiful South Water Street home is ideally located where the road begins its gentle rise up the hill. The original street-facing portion of the residence showcases classic Victorian architecture, complete with a charming covered front porch that reflects its timeless character. Thoughtfully expanded over the years, the home now offers five bedrooms and three bathrooms, providing generous living space while maintaining its historic appeal. Perfectly positioned on a large, beautifully landscaped lot, the property features expansive lawn areas, a majestic shade tree, and glimpses of Edgartown Harbor. A detached garage with a guest house adds flexibility for visitors or extended family, while ample off-street parking enhances convenience. The home is well maintained and presents an exceptional opportunity for thoughtful updates, with plenty of room to add a swimming pool if desired. This is a rare offering that combines historic charm, an outstanding location, and exciting potential.