Development of Old Windermere began in the late 1920s with the opening of the new bridge connecting West Ashley to the Charleston peninsula. After a stall during the Depression, the neighborhood was completed in the 1940s and 1950s after World War II. Old Windermere is conveniently situated around the intersection of Folly Road and Savannah Highway, making travel to downtown Charleston, James Island and the rest of West Ashley easy. Neighborhood streets are quiet with little thru traffic and lined with sidewalks and 90-year-old oak trees, making them picturesque and pedestrian friendly. The eclectic homes in the community are mostly brick, slightly more spacious and situated on larger lots than the homes found in the neighboring Byrnes Down subdivision.