Nestled in the highly desirable Smithtown Pines, this one-of-a-kind home offers a unique layout that's perfect for multigenerational living or for those seeking a spacious, versatile design. With five bedrooms and 4.5 baths, including two primary ensuites, this home offers exceptional accommodations - it's like getting two houses in one! The main home features a large living room that leads to an open dining room and eat-in kitchen. The kitchen is equipped with a center island and Silestone countertops, offering both functionality and style. Just a few steps up, the oversized primary ensuite (15'1" x 30'11") awaits, complete with a full bathroom and the convenience of an in-suite washer and dryer. You will also find two additional bedrooms with a full hall bathroom. The secondary living space area boasts an open floor plan which includes a cozy living room with fireplace, dining room, summer kitchen, and separate laundry area and full bathroom. Upstairs, two bedrooms provide private retreats, one with its own ensuite bathroom and dual closets. Set on a private 0.53-acre lot, the backyard is perfect for entertaining. It features a paver patio, an expansive deck with a screened gazebo, and an inviting inground pool. Plus, the property backs the local Park, ensuring complete privacy in a serene setting. Enjoy proximity to Blydenburgh Park and the Town of Smithtown beaches, where outdoor recreation is just moments away. 99 Shirley Ct presents a rare opportunity in the Pines- a perfect blend of elegance, functionality, and tranquility. Whether you need two separate living areas or one large home, this house can accommodate. Don't miss this thoughtfully crafted, one-of-a-kind home!