Welcome to this well-maintained, mid-century brick two-flat in the charming Gladstone Park neighborhood! Situated on a unique lot along a quiet, tree-lined street, this property offers an oversized fenced backyard, beautiful landscaping, and an incredible opportunity for owner-occupants or investors alike. Lovingly cared for by only its second owners, the building features two spacious units, a finished lower level, generous outdoor space, and numerous updates throughout. Unit 1 offers 2 bedrooms and 2 full bathrooms, duplexed down to a beautifully finished basement completed in 2016. The main level features hardwood floors throughout, an eat-in kitchen updated in 2012 with Brookhaven soft-close cabinetry, stainless steel appliances, and a stylish backsplash, along with Brookhaven cabinetry in the main-level bathroom. The expansive finished lower level provides incredible additional living and entertaining space with taller ceilings, recessed lighting, a second full bathroom, and laundry hookups. Unit 2 offers 3 bedrooms and 1 full bathroom, a spacious eat-in kitchen with a new oven (2025), in-unit stackable washer and dryer, and hardwood floors beneath the newer carpeting. Both units enjoy access to the rear covered porches overlooking the spacious backyard. Major improvements include a new building roof (2025), garage roof (2018), replacement of the majority of windows, three newer rear doors, updated copper plumbing, 200-amp electrical panels, sewer flood control system with outdoor cleanout and sump pump, and tuckpointing completed in 2011. Additional highlights include a detached two-car brick garage with a new garage door opener (2025), professionally landscaped front yard, and plenty of street parking. The location is just as appealing! Nestled in a peaceful pocket of Gladstone Park near Jefferson Park, this home is just one block from the Cook County Forest Preserves and scenic bike trails, with neighborhood parks, schools, restaurants, and shops nearby. Convenient access to Metra, the Jefferson Park Blue Line, and major expressways makes getting around the city a breeze. A wonderful opportunity to own a thoughtfully maintained two-flat with flexible living space, fantastic outdoor areas, and a great neighborhood setting!