Tucked at the end of one of Charleston's most picturesque oak-lined streets in highly sought-after Old Windermere, this beautifully restored nineteen forty brick cottage blends timeless Charleston character with the kind of thoughtful upgrades buyers rarely find executed this well. Inside, original hardwood floors, natural light, and professionally curated finishes create a home that feels both elevated and welcoming. The main house offers four bedrooms and two full bathrooms, with a floorplan that balances classic charm and modern livability. The fully remodeled interior preserves the warmth and personality of the original home while incorporating the updates today's buyers actually value. The kitchen was designed with both function and style in mind, highlighted by a recently renovated custom walk-in pantry with glass door, a standout feature that feels straight out of a designer showcase home. Living spaces flow easily for both everyday life and entertaining, while original architectural details keep the home grounded in its Charleston roots. One of the most compelling features of the property is the detached two-car garage topped by a fully furnished three hundred thirty-six square foot apartment with kitchenette and full bathroom, completed in 2022, and used as a short term rental by the current owners. Whether used as an income-producing rental, private guest suite, home office, or multi-generational living space, it adds flexibility and value that is increasingly difficult to find this close to Downtown Charleston. The outdoor spaces feel equally intentional. A detached fourteen by twenty screened porch with wood-burning fireplace and electrical service creates a true year-round gathering space with unmistakable Lowcountry appeal. Professionally designed landscaping surrounds the property with mature oaks, hydrangeas, tea olives, landscape lighting, and irrigation in both the front and rear yards, giving the home a polished, magazine-worthy feel day and night. Located just minutes from Downtown Charleston, South Windermere Shopping Center, the West Ashley Greenway, Avondale dining, and some of Charleston's most loved local restaurants and shops; this is the kind of home buyers wait for in Old Windermere: classic; updated; flexible; and exceptionally well executed. *Seller is a licensed real estate agent.