Timeless Grayton Beach character meets thoughtful modern renovation in this rare dual residence offering just steps from Western Lake, the shoreline, and the heart of one of 30A's most storied beach villages. Originally built in 1970 and extensively reimagined, the property pairs a gracious main home with a fully detached private cottage, creating flexibility for hosting, multigenerational living, or income potential without sacrificing privacy or charm. The main residence spans approximately 2,910 square feet with five bedrooms and four and a half baths across three levels. Recent updates include a fully redesigned kitchen, renovated bathrooms, fresh interior paint, new flooring, updated wiring and plumbing, two HVAC systems, new appliances, and a new roof. From the inviting front porch, morning coffee is enjoyed with tranquil views toward Western Lake. Inside, the first floor opens to a generous living and dining area that flows seamlessly into the kitchen, which offers ample space for an island and connects to a comfortable sitting or game room. A mudroom off the kitchen adds a half bath, a full sized laundry, and direct access to the side yard for grilling. Two first floor bedrooms feature updated ensuite baths, while a rear hallway leads directly to the backyard. Upstairs, the second level offers two additional bedrooms and two full baths. The third floor serves as a flexible retreat or bedroom, highlighted by a striking wood A frame ceiling with access to the large balcony. The detached cottage provides approximately 560 square feet with one bedroom, one full bath, a family room, a full kitchen, a laundry room, an outdoor shower, and a separate entrance. With a new roof and alley access, the cottage allows easy movement to the beach, lake, and dining while remaining discreetly set apart from the main home. Outdoor living is equally compelling, with a spacious backyard ready for relaxed afternoons, a newly added private pool, curated hardscape, and lush landscaping. After a day on the water, rinse off at the outdoor shower or unwind in one of several private seating areas. Parking is generous with a paver driveway, additional front parking, and two rear spaces for a total of seven. Accessibility has been carefully considered with a ramp on the north side and a fully accessible first floor, including the primary bath. Both residences may be rented separately or together, offering exceptional versatility. Positioned moments from Western Lake, two beach accesses, and iconic spots like The Red Bar, Chiringo, and AJ's Grayton Beach, this is a rare opportunity to own a true Grayton Beach classic where coastal history, modern updates, and an unbeatable walkable setting come together with ease.