Welcome to 1462 W Winnemac #1 - a truly special 4 bed, 3.5 bath duplex down in the heart of Andersonville! With an expansive and thoughtfully designed layout, this home lives like a single-family with soaring ceilings on both levels and an ideal separation of living and sleeping spaces. The main level boasts a seamless flow from the spacious living and dining areas to the open-concept kitchen and spacious family room-perfect for everyday living and effortless entertaining. The kitchen is outfitted with top-of-the-line stainless steel appliances and sleek finishes, sure to impress the most discerning chef. All four bedrooms are situated on the lower level, providing a quiet retreat away from the main living spaces. Thoughtful upgrades by the original owners include custom closets (2022), elegant tray wall paneling in the lower hallway (2024), and a stained & treated rear deck (2023). The recently added bridge to the private garage rooftop (2025) offers easy access to a blank canvas rooftop oasis-ready for your dream deck or turf setup. Enjoy not one but two incredible outdoor spaces: a large deck off the family room and full private roof rights to the garage rooftop. The building has also seen key updates, including a sump pump with backup system and check valve (2023), enhanced landscaping with pavers, fresh sod, and tree installation (2024). Tucked away on a quiet, tree-lined street yet just steps from the vibrant shops, restaurants, and nightlife of Andersonville. A commuter's dream with easy access to the Ravenswood Metra, Argyle Red Line, CTA bus routes (36 & 22), and Divvy bikes. Garage parking included. This is Andersonville living at its finest-don't miss this unique opportunity!