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Offered for the first time in 85 years, the storied home at 424 Ivy Lane is a rare opportunity to own a prominent estate in the heart of Terrell Hills. Built in 1940 by noted architect Bartlett Cocke, this timeless residence spans over 8,000 square feet of grand yet inviting living space, nestled on 2.06 acres beneath majestic heritage oaks. The main home features 4 spacious bedrooms, 3.5 bathrooms, a bespoke library rooted in the home's original design, multiple living areas, and two oversized screened-in porches ideal for relaxing or entertaining. Beautiful parquet hardwood floors run throughout, while French doors in every room-custom-designed and inspired by the Ritz in Paris-bring the outside in, flooding interiors with natural light and garden views. An elevator adds ease and convenience in accessing all three levels of the home. A detached 1,200 sq ft casita includes a full kitchen, living and dining areas, bedroom, full bath, and its own private porch-perfect as a guest house, in-law suite, or private retreat. The charming Rose Cottage pool house offers a full bath and a flexible-use room overlooking the sparkling swimming pool. The grounds unfold with magical garden settings beneath mature oak canopies, creating a sense of privacy and timeless beauty. A 4-car garage and exceptional potential for thoughtful updates make this a once-in-a-generation offering in one of San Antonio's most prestigious neighborhoods.