Nestled on a charming cul-de-sac in the highly coveted 'Vale of Annandale' enclave of Pasadena's prestigious San Rafael Hills neighborhood, this beautifully reimagined residence blends timeless elegance with modern indoor-outdoor amenities and living. Originally built in 1940 and thoughtfully transformed, the home offers an exceptional layout designed for both everyday comfort and effortless entertaining. From the formal entry with its cathedral ceiling, you are immediately drawn to a spacious living room featuring an elegant fireplace--ideal for both quiet evenings and stylish entertaining with an integrated media screening system. The family room includes custom floor-to-ceiling built-ins and breathtaking views of the lushly landscaped rear grounds. Throughout the home, French doors in the kitchen, dining room, den, and primary bedroom invite natural light and create a seamless connection to the outdoors. The main level offers a beautifully remodeled chef's kitchen that flows into the formal dining room, along with four generous bedrooms and four full bathrooms featuring updated finishes. Notable amenities include: Integrated Technology: Surround sound with built-in speakers inside and out; Smart home features including remote control of pool, spa, lighting, heating and cooling. Wine Cellar: A downstairs space capable of storing 2,000 bottles. Versatile Attic: A bonus 940 sq. ft. finished upper level with storage, a holiday planning and gift-wrapping station, and flexible space for an office, studio, or lounge. The private backyard retreat is an entertainer's dream, featuring a brick patio, built-in gas grill, and an outdoor living room with a fireplace. The grounds also include a sparkling pool with waterfalls, a resort-like spa, a sports court, and a golf putting green. Multiple spaces invite comfort, relaxation and entertaining in a serene, resort-like setting. Ideally located just a few minutes from Old Town Pasadena and the trails of South Arroyo, the Rose Bowl, and DTLA, and in close proximity to beloved local favorites including Little Flower, Stoney Point, San Rafael Park & Library, this unique and exceptional property offers a rare blend of privacy, sophistication, and lifestyle with modern convenience in one of Pasadena's most desirable and prestigious locations. The combined main level, wine cellar and bonus upper level attic space brings a total of 3,821 sq ft making this a highly coveted, unique and rarely available property.