Welcome to 101 Red Oak Court, a beautifully updated 3-bedroom, 2-full-bath home tucked away on a quiet cul-de-sac in the desirable Harbor Hills Estates section of Port Jefferson Village. Set among mature trees, flowering landscape, stone walls, and a charming cedar-shake exterior, this home offers warmth, privacy, and the sought-after North Shore lifestyle. Inside, a welcoming foyer opens to light-filled living and dining spaces with hardwood floors, crown molding, soft neutral tones, and inviting natural views from nearly every window. The floor plan offers a comfortable living room, dedicated dining area, spacious open granite kitchen, breakfast nook, and three well-proportioned bedrooms, including a primary bedroom with convenient access to two full baths nearby. The kitchen and breakfast nook create an easy everyday flow, enhanced by a fireplace, skylight, and serene wooded backdrop. Outdoor living is a true highlight, with an expansive rear deck designed for entertaining, dining, relaxing, and enjoying the lush natural surroundings. A private driveway and attached garage add convenience. Located minutes from Port Jefferson Harbor, the Port Jefferson Ferry, train station, marinas, restaurants, and boutique shopping. Enjoy exclusive Port Jefferson Village amenities, including private village beaches, access to Port Jefferson Country Club with golf, tennis, dining, and water views, plus Village Constable services. Conveniently located near Mather Hospital, St. Charles Hospital, and Stony Brook University Hospital. A rare opportunity to enjoy comfort, charm, and the very best of Port Jefferson Village living.