Freeport | Tucked away mid-block on a quiet cul-de-sac in the highly desirable South Freeport waterfront community, 539 Nassau Avenue presents a rare opportunity to experience elevated coastal living with direct canal access just moments from the open bay. Ideally positioned near the renowned Nautical Mile, this meticulously maintained OVERSIZED hi-ranch seamlessly blends lifestyle, functionality, and year-round enjoyment. Designed for boating enthusiasts, the property features a private dock, accommodating up to a 38-foot vessel, along with a dedicated jet ski dock—offering effortless access to the water and endless days spent along the South Shore. The brand-new vinyl bulkhead provides peace of mind. Whether heading out for a sunset cruise or a quick trip to waterfront dining, this location delivers the ultimate marine lifestyle. The upper level showcases a thoughtfully renovated open-concept layout, where a sunlit living room flows into a spacious dining area and a modern kitchen outfitted with stainless steel appliances, a granite center island, and abundant cabinetry. This level offers three bedrooms, including an oversized primary suite complete with a rare en-suite full bathroom and custom closet organization. A second full bathroom and access to a walk-out deck complete this floor, creating the perfect setting for indoor-outdoor living. The lower level offers exceptional versatility, featuring an oversized fourth bedroom, a dedicated laundry room, and an inviting den with a built-in wet bar—ideal for entertaining. A bright and airy sunroom/Florida room, filled with natural light creates a private retreat for relaxation in every season. The outdoor space is equally impressive, designed with both entertaining and everyday enjoyment in mind. A beautifully maintained backyard features Trex decking, multiple seating areas, and a fully equipped outdoor kitchen with a built-in gas grill and pizza oven. A gazebo-covered firepit adds to the ambiance, while the serene waterfront setting enhances every gathering. Additional highlights include a charming front-yard fish pond with lush landscaping, a two-car paver driveway, updated gas heating systems, and the added benefit of residing within the Village of Freeport, known for its independent utilities, including its own electric grid, water system, sanitation services, and police department. A true waterfront gem offering space, upgrades, and an unbeatable location—this is South Freeport living at its finest.