This charming 2.5-storey home is perfectly situated in the heart of Central Hamilton, just steps from the vibrant beauty of Gage Park. This thoughtfully updated residence blends timeless character w/ modern conveniences, offering 3 bdrms, 2.5 baths, & quality upgrades throughout. The inviting covered front porch sets the tone for this warm & welcoming home. Step into a spacious foyer that flows seamlessly into the open-concept living & dining room, where pot lighting illuminates rich updated flooring & a striking feature wall adds depth & style. The updated kitchen features white cabinetry, S/S appliances, butcher block countertops, & a classic yet modern aesthetic - ideal for family meals or entertaining. A piano-style staircase leads to the 2nd level where youll find two generous bedrooms, including one with a charming bay window that floods the room with natural light. An exterior door on this level offers access to the flat roof over the kitchen - a space brimming with potential. The gorgeous 3-piece bathroom features an oversized glass shower with elegant finishes. The third level is a true primary retreat, offering two closets and a spa-inspired 3-piece bathroom with a luxurious stand-up glass shower. The unspoiled lower level provides excellent storage space, laundry facilities, and a finished 2-piece powder room. Enjoy a low-maintenance rear yard with turf and a deck, leading directly into the oversized 1.5-car garage with an updated door. Recent updates include windows, roof shingles & eavestroughs (2017), flooring & light fixtures (2020), central air conditioning (2020), electrical panel (2020), replaced main cast iron drain (2020), and furnace (2023). California shutters and oversized mouldings throughout preserve the homes original charm while offering modern functionality. With a walkable lifestyle at your doorstep - cafés, shops, and quick access to major transit - 39 East Bend Avenue South is the perfect blend of location, character, and upgrades.