Welcome to 290 Hillside Drive, a thoughtfully updated semi-detached home tucked into one of Mississauga's most established pockets of Streetsville. Set on an extra-long 140' lot with mature trees and rare rear privacy, this home blends functional family living with the charm of "The Village in the City." Inside, hardwood flooring carries through the main floor, upper landing, and stairs, while large windows and a bright bay window fill the living spaces with natural light. The spacious living room walks out to a landscaped backyard designed for quiet evenings and summer entertaining, complete with a pergola, front and rear sprinkler system, deck, and timed outdoor lighting.The eat-in kitchen features stainless steel appliances, a stone backsplash, black glass cooktop, wall oven and ample cabinetry, with a separate dining room ideal for hosting. Upstairs, the primary retreat overlooks the serene backyard and includes an updated 5-piece ensuite with quartz counters, tiled floors, wainscoting, and a walk-in shower (2021). The updated main bath echoes the same elevated finishes, while the oversized second-floor laundry room adds everyday practicality. The finished lower level with a second kitchen, gas fireplace, built-in desk, and additional living space offers flexibility at home or with guests. Major updates include roof (2025), and hot water tank (2025) furnace and A/C (2018), and windows (2010). With parking for 4 in the driveway plus a 2-car attached garage, and a 7-minute walk to the Streetsville GO Station, this location offers seamless access to GO Transit, Highways 401, 403, and 407, and a short hop to Streetsville's beloved local shops, restaurants, parks, trails, and top-rated schools.