Tucked away in a quiet cul de sac on a sprawling double lot beneath majestic oaks, this nearly 5,000 sq ft timeless 2 story residence blends classic elegance with modern luxury. Perfectly positioned on the first hole of one of Sarasotas most sought after golf courses, the home showcases soaring 11 ft ceilings, gleaming marble floors, and dazzling crystal chandeliers. A Louis XVI fireplace anchors the dramatic sunken living room, while French doors and expansive windows flood the sunroom with natural light and frame sweeping golf course views. Step outside to three inviting patiosideal for sunset cocktails, lively gatherings, or peaceful mornings overlooking the greens. A brick path winds through lush, manicured gardens to the expansive guest house, creating a true family compound that offers exceptional flexibility for hosting guests or multigenerational living. The nearly 2,000 sq ft guest house features 2 bedrooms, 2 en suite bathrooms, a generous living room, dining room, outdoor kitchen, and a private laundry room. Overlooking the sparkling pool and spa, this retreat combines privacy with convenienceperfect for extended stays, visiting family, or an in law suite. The Oaks Club elevates the lifestyle even further with two 18 hole championship golf courses, fitness center, exceptional dining options, a vibrant calendar of social events, and world class tennis and pickleball facilities. Ideally located near Casey Key and the powdery white sands of Siesta Key, and just a short drive to Downtown Sarasotas thriving arts scene and the boutiques of St. Armands Circle. Membership at The Oaks is required.