Welcome to 75 Osprey Point, a residence that epitomizes timeless elegance and thoughtful design within the prestigious Oaks Bayside. On two expansive lots totaling over three-quarters of an acre, this architectural estate was originally designed by renowned architect Bo MacEwen, the visionary behind The Oaks iconic clubhouse. A harmonious blend of traditional sophistication and modern updates awaits, with lush Selby-like grounds and serene lake views enhancing the ambiance. The circular drive with pavers leading to a charming tile-front porch invites you to explore the grand interiors. Step through the entrance into a dramatic foyer featuring large-format tile flooring, soaring ceilings with a skylight, intricate crown molding and custom trim details adorning the walls. Lighted art niches provide the ideal setting for showcasing your favorite pieces. The living spaces exude a welcoming grandeur. The family room boasts a custom tray ceiling, a fireplace flanked by built-ins and elegant archways with detailed trim. The stately living room features bay windows framing a cozy seating area with built-in benches, while French doors lead to a secluded patio for moments of quiet retreat. The dining room is equally exquisite, with a tray ceiling, crown molding and sophisticated architectural detailing. The updated eat-in kitchen is a chef's dream, seamlessly blending style and function. Highlights include sleek gray cabinetry, quartz countertops, gold-accented tile backsplash, under-cabinet lighting and premium appliances such as a Sub-Zero cabinet-faced refrigerator, KitchenAid dishwasher, and a Samsung range and microwave. Two custom-organized pantries and an additional Sub-Zero refrigerator provide ample storage. The main house offers three generously appointed guest rooms, each with soaring ceilings, crown molding and custom trim details. Guest baths each feature refined finishes. A separate guest house, equipped with its own HVAC system, offers studio-style accommodations complete with a kitchenette which is ideal for visiting family or friends. Outdoor living is elevated with a gorgeous open-air pool surrounded by lush landscaping, creating a private oasis. The grounds are illuminated with landscape lighting, showcasing the beauty of this estate after sunset. As a resident of Oaks Bayside, you'll enjoy access to a private dock on the Intracoastal Waterway, offering breathtaking views and serene sunsets. The Oaks Club membership is mandatory and provides world-class amenities, including two championship golf courses, 12 Har-Tru tennis courts, a state-of-the-art fitness center, a Junior Olympic heated pool, croquet, pickleball and a variety of dining options. Conveniently near Pine View School, the Legacy Bike Trail, pristine Gulf Coast beaches and downtown Sarasota, this property is a gateway to the best of Florida living. Discover the unparalleled lifestyle and refined elegance of 75 Osprey Point, a home that stands apart in every detail.