Set within the private, guard-gated equestrian city of Rolling Hills, an extraordinary offering unfolds across two adjoining properties on a private cul-de-sac—fourteen and sixteen Johns Canyon Road—now available simultaneously for a once-in-a-lifetime chance to create a combined estate of exceptional scale and potential. Fourteen Johns Canyon Road presents a legacy property rooted in the historic Rancho Elastico. Originally constructed in nineteen twenty-six as a ranch bunkhouse and thoughtfully expanded over time, the residence has evolved into a substantial multi-wing home centered around an open courtyard, blending original character with later additions, for a highly flexible floorplan. The formal entry with powder room opens to a spacious living room with soaring wood-beam ceilings, a Palos Verdes stone fireplace, and French doors to a patio. The formal dining room is well connected to the kitchen, featuring a center island, pantry, and breakfast nook with access to the courtyard for indoor-outdoor living. An open hall with an adjoining study leads to the original portion of the home, where a library, additional living area, second kitchen, bedroom, full bathroom, and office nook provide space for a variety of uses. The home continues with a wing including two bedrooms, a shared bathroom, and nearby laundry room. A spacious primary suite features a five-piece bathroom and cedar-lined closets. A large basement with interior and exterior access is well-suited for a gym, studio or workshop. The grounds reflect rich equestrian and lifestyle heritage, with multiple horse stalls and runs, expansive lawns, mature shade trees, and various gardens and open spaces. Outdoor features include multiple gathering areas, barbecue patios, an enclosed yard with playhouse; freestanding writing retreat; and areas previously used for animal care and rehabilitation contributing to the property's unique and meaningful history. The showstopper is converted concrete barn reimagined as two-level saloon entertainment venue complete with stage lighting sound systems bar balcony restroom offers truly one-of-a-kind setting for private events performances or creative pursuits. The driveway continues to the adjacent parcel at sixteen Johns Canyon Road also available. Together these two properties create rare opportunity to establish private compound or legacy estate—where history space privacy vision converge in one of South Bay's most exclusive distinctive communities.