Exceptional single-family home with legal ADU in the Deering Highlands. This iconic property offers a rare combination of historic character and modern updates, ideal for investors or owner-occupants seeking rental income. Each unit features a beautifully renovated kitchen, natural gas heat and hot water, two full bathrooms, separate in-unit laundry, and newly refinished hardwood floors. Additional highlights include a newer roof, fireplace insert, quartz countertops, a two-bay garage, and a large fenced-in yard. Additional finished living space on the third floor and in the basement provides flexible options for expanded living areas, home offices, or guest accommodations, enhancing both functionality and rental appeal. The driveway is accessed from Orland Street, offering easy garage access and excellent utilization of the generous lot. The City of Portland has indicated the parcel may be large enough, with sufficient road frontage, to be subdivided into two conforming lots-adding future development or value-add potential. Showings begin February 14th. Open houses February 14th & 15th from 12:00-2:00 PM.