4227 N Ashland Avenue Welcome to this classic Lakeview Greystone 3-flat, where vintage charm meets modern conveniences! Units 1F and 2 boast soaring 10-foot ceilings, beautiful hardwood floors, original woodwork, separate dining rooms, and generously sized bedrooms with ample closet space, and can comfortably accommodate queen-size beds. Unit 2 also offers a private rear deck, perfect for morning coffee or relaxing on summer evenings. Thoughtfully updated over the years, the building features renovated kitchens and bathrooms, newer windows, a new roof installed in 2024, separate utilities, central heating and air conditioning in the front first-floor and second-floor unit, and central heating in the rear first-floor unit. Additional amenities include shared basement laundry. The extra-deep lot (150' x 31') provides generous outdoor space, a detached two-car garage, plus an additional parking pad. With approximately 7.5-foot basement ceilings, there's exciting potential to duplex down or explore the possibility of an accessory dwelling unit (ADU) for additional rental income. Ideally situated in the vibrant Lakeview/Ravenswood neighborhood, you'll enjoy tree-lined streets, neighborhood restaurants, boutique shopping, and convenient access to the CTA Brown Line. The Southport Corridor, Wrigley Field, Lincoln Square, and North Center are all nearby, offering an abundance of dining, shopping, and entertainment options. Whether you're looking for an investment property or an opportunity to live in one unit while generating rental income from the others, this classic Chicago Greystone offers exceptional versatility in a sought-after neighborhood. Schedule your showing today!