First time hitting the market in nearly 50 years and sitting prominently at the crest in the coveted Westwood Highlands on an extra wide lot, 221 Cresta Vista Drive showcases sweeping Bay-to-Ocean views and dazzling city lights from multiple levels. This spacious, custom mid-century residence has been well enjoyed and expanded in the year 2000 on all sides with permits and blends timeless architecture with thoughtful modern updates across three spacious levels of living. Sun-drenched and south-facing, the home features refinished hardwood floors, an updated chef's kitchen with pantry, and multiple inviting spaces for entertaining and everyday living. Putting your own design touches can further elevate the space to increase equity - this is a true value play. Main Level: An elegant living and dining area flows seamlessly into the kitchen, breakfast area, and family room opening to a generous deck for effortless indoor-outdoor living. A half bath completes this level. Upper Level: Ultra RARE floorplan with 4 well-appointed bedrooms, including two en suites, 3 updated bathrooms, and two private decks all on the same level! You'll love the breathtaking city+water views. Lower Level: A flexible family room and office space, plus a separate laundry area or guest quarters with a full bath. Street level offers two separate garages. 2023 Roof and 200 AMP Electrical service. Ideally located near West Portal and Monterey Boulevard shopping, Miraloma Park, Glen Park, and Sunnyside Playground, with convenient transit and freeway access. Nearby top-rated schools include Miraloma Elementary, CAIS, Lick-Wilmerding, Riordan, Stratford, Waldorf, Lowell, and Sunnyside. A rare opportunity to own a view-driven retreat offering space, versatility, and refined city living.