Listing courtesy of Legacy Properties Sotheby's International Realty.
Selling Office: Vitalius Real Estate Group, LLC.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.
Listing data is derived in whole or in part from the Maine IDX and is for consumers' personal,noncommercial use only. Dimensions are approximate and not guaranteed. All data should be independently verified. © 2026 Maine Real Estate Information System, Inc. All Rights Reserved.
This information is provided exclusively for consumers' personal, non-commerical use and may not be used for any purpose other than to identify prospective properties consumers may be intrested in purchasing.


Privacy Policy
Your privacy on the Internet is important to us. This Privacy Statement is to inform you that we will not provide your personal information to any third parties except as required by law or expressly authorized by you. We do not sell, trade, barter, or share information obtained from use of this site with any other businesses or people. All information gathered from a visitor to this web site is used solely by this office and/or its affiliated licensee(s). For additional information, please contact this office.
Contact: