A grand estate where timeless design meets lakefront tranquility, 101 Osprey Point Drive offers refined living within the private gates of The Oaks Bayside. Designed by architect Bo MacEwen, this one of a kind home spans more than 5,000 square feet, all cleverly positioned on nearly an acre with 150 feet of lakefront. Situated on two of the communitys most desirable lots, the residence balances architectural distinction with thoughtful updates that ensure comfort and livability. An oversized circular drive paved in granite tile leads to a stately double door entrance. Inside, the foyer sets the tone with soaring ceilings, hand crafted moldings, chandeliers, and a white onyx floor with marble inserts. Spaces include an oversized living room with dual fireplaces, a crystal chandelier, and multiple sets of French doors opening to the lakefront patio. The dining room, anchored by another fireplace and framed by custom casings and built in shelving, is ideal for grand entertaining. A domed ceiling sitting room with French doors to the patio adds an intimate space for cocktails or conversation, while the custom bar and wine room, with etched glass cabinetry, stone counters, and display shelving, enhances the homes appeal for gatherings. The kitchen, completely remodeled in 2019, is a showcase of craftsmanship with UltraKraft cabinetry, custom soffit lighting, Corian countertops, and a center island with breakfast bar. Luxury appliances include a Sub Zero refrigerator, Wolf gas cooktop, wall oven, microwave, warming drawer, two KitchenAid dishwashers, and a Frigidaire wine fridge. A butlers pantry provides additional storage, while the sunny breakfast nook overlooks lush gardens. Family and gathering rooms carry the same sense of scale, with dramatic fireplaces, intricate moldings, and detailed ceiling treatments that flow seamlessly for everyday living or large scale entertaining. The primary suite is a true retreat with a spacious sitting area, custom closets, and a well appointed bathroom that was newly remodeled in 2025 with spa inspired finishes. Three guest suites, each with updated full baths (2021 and 2025), provide privacy and comfort. One is a suite with a bathroom near the laundry room, which offers flexibility for live in staff or extra accommodation. Outdoors, the home embraces its setting with an open pool, expansive deck, and cabana surrounded by manicured hedges and mature landscaping. The views are equally compelling, with mature gardens and community reflecting pond in the front and sweeping lake vistas in the back. Additional highlights include a three car garage, refinished hardwood floors (2020), and a new Daikin 5 ton AC system installed in 2022. Ownership at The Oaks Club brings an unmatched lifestyle, with two championship golf courses, tennis and pickleball courts, croquet, a fitness center and spa, three on site restaurants, and a community dock on Little Sarasota Bay. Elegant yet inviting, 101 Osprey Point Drive stands as a rare opportunity to enjoy lakefront living with resort style amenities in one of Sarasotas most established private enclaves.