A rare opportunity to reimagine a historic waterfront property with incredible potential. Set along the Stroudwater and Fore Rivers with access to Casco Bay, this unique offering combines a peaceful, tucked-away setting with a highly convenient location just minutes from Portland's amenities. Known as the Isaac Fly House, this Colonial-era home dates back to approximately 1730 and may be among the oldest residences in Portland. Rich in history and character, it remains a notable presence in the city's historic Stroudwater Village. Enhancing its potential, the property includes a thoughtfully designed construction set by Scott Simons that previously received approval from the Portland Historic Preservation Board (approval has since expired and would require reapplication). The plans envision meaningful additions and exterior/site improvements, including a garage and expanded living space, and are complemented by renderings that help bring the vision to life. The property was also surveyed in 2020. Originally built as a single-family residence, the home is currently configured as a two-unit property, with two-bedroom, one-bath units on each level. This flexible layout lends itself to a variety of uses, including multi-generational living, rental income, or conversion back to a single-family home. Situated on over a third of an acre, the lot offers ample space for expansion and site enhancements. The interior and exterior need significant improvement; the seller obtained quotes for the basement, roof, siding, and trim replacement, though no work has been completed. Buyers are encouraged to perform their own due diligence. Enjoy striking sunrise views and a setting that feels worlds away--where evenings are accompanied by the sound of the falls and days invite kayaking to Thompson's Point for waterfront concerts or exploring the nearby Fore River Preserve trails.