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 a fireplace, dining room, summer kitchen, 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!,