Nestled in a private community of just eleven homes, this exceptional estate in the highly sought-after Town of Windermere offers a rare blend of luxury, functionality, and versatility. Situated on over an acre, this stunning pool home provides two distinct living options: a 4,018-square-foot residence with two master bedrooms or a nearly 3,000-square-foot main home with an additional 1,100-square-foot private in-law suite, making it ideal for multigenerational living. A standout feature of this residence is the expansive 1,100-square-foot in-law suite, designed for both comfort and independence. It boasts a private entrance, full kitchen, spacious living room, large walk-in closet, and a dedicated air-conditioned zone. Sliding glass doors open directly to the enclosed pool area, seamlessly blending privacy with accessibility to the main home. With over $300,000 in upgrades, this home has been enhanced with thoughtful improvements and premium finishes. The lifetime metal roof, backed by a 50-year guarantee, is designed to resemble shake roofing while offering top-tier durability. Structural enhancements include a rebuilt front porch, a redesigned entrance, and a garage pad designed for enclosure, constructed with footers, allowing for an effortless conversion into a fourth bay if desired. Inside, carefully selected materials create a warm and inviting ambiance. Porcelain tile extends through the family room, kitchen, and laundry, while mahogany flooring enriches the living room, hallway, and dining area. The bedrooms feature engineered hardwood or vinyl flooring, and the loft offers additional potential with pre-installed plumbing for a future wet bar or bathroom. The kitchen was fully renovated in 2017, designed for both elegance and everyday functionality, while the guest bathroom was remodeled just two years ago. The home is equipped with three separate HVAC zones, ensuring year-round comfort. Two water heater systems efficiently serve different areas of the home, and outdoor kitchen plumbing is available in two locations, perfect for those who enjoy entertaining by the pool. Stepping outside, the backyard has been transformed into a private oasis. The pool deck was resurfaced, resealed, and rescreened within the last year, and a newly added fire pit provides a cozy gathering space. This residence offers exclusive access to Lake Butler and Windermere’s charming amenities, including tennis courts, a town hall, recreational spaces, and access to multiple lakes. Located in a tranquil setting with two cul-de-sacs, this small gated HOA community ensures a peaceful and private lifestyle. With extensive upgrades, a flexible layout, and a prime location, this home is truly a rare find in Windermere.