Beautifully positioned within Sarasota's elite country club The Oaks, this sophisticated, multi-level Key West-style home reflects the best in bespoke design. Driving into The Oaks, you'll instantly feel the privacy and attention to detail that sets this community apart from all others. Meandering roads under a canopy of native Oaks, Palms and Pines wind past exquisite single-family residences. The Oaks Bayside community is adjacent to Historic Spanish Point's nature preserve and the bayfront, affording the lucky residents of 144 Osprey Point Drive a prime protected location with striking sunset views. Master craftsmenship is evident throughout the home's three levels, with rich wood floors that connect main living spaces, soaring ceilings with exposed beams and a wraparound balcony that gives every member of the household views of the area's cherished wildlife. The gourmet kitchen is an epicurean delight with massive center island with bar seating and gas range; abundant cream cabinetry; wine refrigerator and breakfast nook overlooking the mangroves. Perfect for everyday living and entertaining, choose to dine indoors in the formal dining room, or opt for dinner under a blanket of stars on the open-air pool terrace with fully equppied and covered summer kitchen. Retreat to the master suite for the best in self-care with balcony access, marble spa bath and custom walk-in closet. Two additional guest suites allow the owner flexibility to covert one or both into a gym, office or den, and a secondary master suite with full kitchen and laundry boasts it's own wing. A drive-through motorcourt leads to two oversized garages with ample storage for all your automotive and recreational needs. A few homes down, a boat dock and kayak launch let you explore the area's mangrove tunnels and waterways. The Oaks is one of the most highly-regarded communities on Florida's Gulf Coast. Unrivaled amenities include two championship golf courses, a premier tennis program acknowledged by the International Tennis Federation, refined dining experiences, a wellness club that attends to body and spirit, croquet court, active social calendar and more. Owners within The Oaks Bayside are required to have a social or equity membership.