A rare opportunity to own an estate property on one of Old Oakville's most prestigious streets. Set on an oversized 100' x 171' lot, this David Small-designed home offers over 8,000 square feet of finished living space, ideal for modern family living and entertaining. Just a short walk to downtown Oakville and minutes to the GO Train, Whole Foods, Longo's, and top-ranked schools, this home offers both convenience and privacy. Surrounded by mature trees, the property sits on a quiet, established street. Inside, the double-height foyer opens to formal living and dining rooms. The main level features oversized principal rooms with vaulted ceilings. The chef's kitchen flows into the family room and includes a large island, premium appliances, and custom cabinetry. A mudroom with front and rear access, a secondary powder room for pool use, and main floor laundry add everyday practicality. Upstairs, the primary suite offers a spa-like ensuite with steam shower and soaker tub. Three additional bedrooms include ensuite access and ample closets. A second-floor family room offers flexible space for growing families. The finished basement includes a large recreation room, games area with wet bar, oversized wine cellar, newly finished gym, fifth bedroom, and full bathroom. Outside, the private backyard is fully landscaped with a pool, retractable cover, hot tub, covered lounge, and built-in outdoor kitchen-ideal for relaxing or entertaining. With parking for six vehicles and an oversized double garage, this is a timeless family home in one of South Oakville's most desirable locations.