Welcome to 17 E Oak Street, a rare income-producing historic gem in the heart of Old Town Canal Winchester situated on almost a 1/2 acre. Featuring timeless character, multiple fireplaces, and true all-brick construction—including beautiful brick floors—this 2,800 sq ft residence blends architectural charm with modern livability. The main home which brings a Tuscan/Italian Villa feel with Courtyard Ambience. This rare European style home offers two spacious living/family rooms, perfect for entertaining, relaxing, or creating separate gathering spaces. Rich hardwood/brick floors, original details, and abundant natural light add warmth and character throughout. A large bonus room at the rear of the home provides incredible versatility—ideal for storage, a workshop, a sunroom, or convert to an attached garage or whatever fits your lifestyle. Outside you will find the home surrounded by a private courtyard with multiple areas to enjoy a peaceful escape or a unique place to entertain. Outside, two well-maintained 840 sq ft efficiency apartments sit privately behind the main home, each with separate entrances and kitchens. These units currently produce $900 and $750 per month. Perfect for owner-occupants wanting mortgage offset or investors seeking long-term cash flow. This entire property is situated on almost an 1/2 acre and surrounded by a stone wall which gives a courtyard feel that brings richness and privacy. Situated just steps from the historic Train Depot & Mill museum/event center, and walking distance to restaurants, breweries, and downtown shops, this property sits in one of Central Ohio's most charming, walkable districts. With its unique mix of character, size, rental income, and prime location, opportunities like this rarely come to market.