Looking for a multi-family property with built-in rental income potential? This unique opportunity in Portland offers two separate residences on 1.23 level, fenced acres, tucked in a quiet neighborhood just minutes from downtown, golf, and the Connecticut River. The main residence spans 3,620 sq ft and features 4 bedrooms, 3.1 bathrooms, and significant updates throughout-including a new roof (2014), a propane boiler with on-demand hot water (2025), and energy-efficient mini splits. The kitchen and dining area open to a composite deck added in 2024, leading to a screened-in gazebo with electricity-perfect for relaxing or entertaining. The second home is a 915 sq ft Ranch-style residence with its own entrance, 1 bedroom, 1 full bath, and an open-concept layout. Whether you're looking to generate passive income, house extended family, or occupy one unit and rent the other, the setup is ready for flexible use. The property also includes a barn/workshop with electricity and lofted storage-great for additional storage or creative use. Well cared for and improved over the last 16 years, this property combines historic charm with income-producing potential-ideal for owner-occupants, investors, or multi-generational living.