Charming family home in the coveted John Fraser/Aloysius Gonzaga school catchment - perfect for young families seeking top schools and easy commuting. The family has been lovingly maintaining the property since 1990 & are ready to pass the torch to the next lucky family. 5296 Middlebury Drive offers 2,819 sq ft of finished living space, plus 1346 sq ft of unfinished lower level space. Great flow and energy w/generously sized rooms, ideal for growing households. Upgrades and features include: Oak hardwood staircase, Oak hardwood floors in the living & dining room. The family room has a cozy gas fireplace & hardwood floors. Updated kitchen (2019) w/quality stainless appliances, double door fridge w/ice & water dispenser, quartz counters and a large table height work/eat-at island overlooking the sunny, private backyard, great for kids and summer relaxation. Convenient main-floor laundry and inside access to the double garage. Huge principal suite, w/renovated spa like ensuite bath (2020) featuring walk-in glass shower w/ a linear drain, separate oval soaker tub & a double sink vanity w/quartz counters. Main bathroom also remodelled in 2020. Side-door with direct access to the unblemished basement - excellent opportunity to create an in-law or income producing suite. Interlocking patio (2023), mature perennial landscaping & established trees. Mechanicals: Attic Insulation upgrade to R50 (2023), Roof Shingles (2007); windows and front door (2010); furnace & AC (2008), Basement waterproofing 2012 & 2018.This prime location offers conveniences within a few minutes' walk to Erin Mills Town Centre, Library, Community Centre, restaurants, grocery stores, trails, dog park, & multiple elementary/secondary schools. Quick commuter access to highways 403 / 407 / 401 and just ~7 minutes to Streetsville GO by car. This move-in-ready gem offers tonnes of space, updates, and a family-focused neighbourhood. PICTURES ARE VIRTUALLY STAGED.