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105 Woodside Drive captures the very best of Country Club Living in Greenwich. Chic fieldstone classic set within the gated Milbrook community, home to the coveted Milbrook Club, with the opportunity to apply for private membership--creating a lifestyle where recreation, relaxation, and social life are just moments from your front door. Perfectly sited overlooking the lake on nearly an acre, the six-bedroom residence blends modern interiors with an effortless indoor-outdoor flow designed for entertaining and everyday enjoyment. Renovated and expanded for seamless living, the crisp, light-filled residence unfolds across four levels, highlighted by a spectacular great room with soaring 19-foot ceilings, elegant formal rooms, and a welcoming family room that opens to a gourmet kitchen with center island, professional appliances and a sunny breakfast room. French doors lead to terraces and a lush backyard--an inviting setting for outdoor dining, gatherings, and play. Upstairs, the serene primary suite offers generous walk-in closets and two luxurious baths, accompanied by three additional ensuite bedrooms. A versatile top floor provides two more bedrooms or a creative retreat, while the finished lower level (additional 1500+ sq ft) has another media area, gym, wine space and much more.