Conceived for the entertaining traditions of the 1920s and thoughtfully adapted for modern life, this architecturally significant Gold Coast penthouse offers approximately 7,750 sqft of gracious living space. With only three owners, this residence carries notable provenance, including time as the home of silent film icon Colleen Moore and reputed dinners attended by John F. Kennedy in the grand dining room. The main level is designed for both large-scale entertaining and daily living. The dramatic two-story living room features a wood-burning fireplace, linenfold paneling, an ornamental plaster barrel-vault ceiling, and oversized windows that open directly to a rare 61-foot private terrace, an exceptional feature seldom found in the Gold Coast. The paneled dining room comfortably accommodates gatherings of more than 20 guests, while the adjoining sunroom offers a more intimate setting. A richly paneled library includes a gas fireplace and the original speakeasy-style bar concealed behind movable bookcases, complemented by a second bar by the dining room. A spacious white eat-in kitchen opens to a family room and office with custom built-ins, a beamed ceiling, and a gas fireplace. Five bedrooms, 5 full baths, and 2 half baths provide excellent flexibility across two levels. The primary suite includes a gas fireplace, dual dressing rooms, and an elegant bath finished with oversized book-matched marble slabs. Additional features include a large playroom, dual laundry centers, a temperature-controlled wine closet, and generous storage. Building amenities include full-time door and engineering staff, an on-site manager, a newly renovated exercise room, and a fabulous landscaped garden terrace. Valet parking for multiple vehicles is available directly across the street. Ideally located near parks and playgrounds, acclaimed public and private schools, premier dining and shopping, and lakefront recreation, this penthouse offers a rare combination of scale, outdoor living, and architectural distinction in the heart of the Gold Coast.