Tucked within the highly desirable Three Oaks neighborhood of Sarasota, 5619 Oak Grove Court is nestled in a serene enclave known for its namesake tradition: each home was originally required to be accompanied by the planting of three oak trees, creating a lush, shaded community rich in character and charm. Positioned on a spacious, nearly 12,000-square-foot lot at the end of a quiet cul-de-sac, this 4-bedroom, 2-bath, 2,422-square-foot residence offers both tranquility and functionality—ideal for growing families, seasonal residents, or anyone in search of a true Florida pool home with room to breathe. Enjoy peaceful mornings in your northeast-facing backyard, where filtered sunrises peek through majestic mature oaks and reflect on the sparkling, oversized pool. The fully fenced yard provides privacy and security for children or pets, while the generous covered lanai sets the stage for effortless outdoor living—from poolside lounging to casual dinners under the stars. Evening strolls through this quiet, low-traffic neighborhood are complemented by glowing sunsets from your front door, all within the safety and value of Zone X—no flood insurance required, and no history of storm damage. This home is also free of CDD fees, offering added savings and peace of mind. Built with durable concrete block masonry and cement-based stucco, the home has been well maintained and thoughtfully updated over the years. Inside, a bright and open layout connects the formal living and dining spaces with a central kitchen and a comfortable family room. The kitchen offers a closet pantry, reverse osmosis for the sink, fridge and ice maker, ample counter space, and a clear view of the pool, allowing for seamless indoor-outdoor living. Sliding glass doors from the primary suite, formal living room, and family room invite natural light throughout and strengthen the connection to the beautiful backyard oasis. The split-bedroom layout features four bedrooms and two full baths, with the fourth bedroom currently serving as a home office or den. With its own closet, it can easily convert into a private guest suite or creative flex space. Notable improvements include a new HVAC system installed in 2023, saltwater pool conversion and resurfacing completed in 2019, and hurricane shutters added in 2021. The roof, a hip-style barrel tile, dates to 1999 but benefits from a tax-effective year of 2004. Additional updates include a new electrical panel in 2019, a water heater from 2016, new washer and dryer in 2019, and updated flooring in three bedrooms and the office/den. The home was freshly painted, power-washed, and professionally landscaped in 2025, further enhancing its curb appeal. Practical touches like the raised AC handler in the garage ceiling for quieter operation and more interior space, pull-down attic storage, and a built-in workstation in the oversized garage make this home as functional as it is beautiful. Located within an A+ rated Sarasota school district and just minutes from I-75, The Legacy Trail, premier shopping, and the world-renowned beaches of Siesta Key, 5619 Oak Grove Court presents the perfect balance of lifestyle, location, and long-term livability. Whether you're snowbirding, raising a family, or simply looking for a peaceful place to call home, this thoughtfully designed and impeccably maintained property checks every box.