Nestled in the vibrant heart of Winnetka, 1004 Oak Street is a 2015-built, Nantucket-style masterpiece that redefines luxury living. Perfectly positioned just steps from the train, charming downtown, acclaimed restaurants, serene parks, and top-rated schools, this custom home on an oversized corner lot seamlessly blends timeless elegance with everyday functionality. The exterior stuns with classic cedar shake siding, premium windows, lush landscaping, and a fully fenced yard. The private backyard retreat is ideal for year-round entertaining, featuring a built-in outdoor kitchen, custom firepit, secondary fireplace, outdoor TV, multiple bluestone patios, and beautifully designed green space. Inside, refined craftsmanship abounds-10-foot ceilings, rich hardwood floors, detailed custom millwork, and integrated speaker systems set a sophisticated tone throughout the main level. The open-concept floor plan includes a gracious living room and formal dining room, ideal for elegant entertaining. A handsome office with custom built-ins provides a quiet workspace, while a spacious mudroom adds everyday convenience. Anchored by a fireplace, the inviting family room flows effortlessly into the chef's kitchen, which features soft-close cabinetry, an oversized island, dual Sub-Zero refrigerator and freezer, Wolf double oven, built-in microwave, and a sun-drenched breakfast room. Upstairs, the second and third floors offer four spacious bedrooms, each with en suite bathrooms and custom closets. The luxurious primary suite includes dual walk-in closets, a private balcony, and a spa-inspired marble bathroom with soaking tub, oversized shower, dual vanities, and marble countertops. A full second-floor laundry room completes the upper level. The finished lower level elevates the home's entertaining appeal, featuring a sleek bar, wine room, large recreation space, fitness room, fifth bedroom, full bath, and abundant storage. With classic design, generous living space, and a premier in-town location, 1004 Oak Street is a rare sanctuary in one of the North Shore's most coveted communities.