Rare 1917 Transitional Craftsman with stunning renovations, situated on a quiet tree-lined street under towering palms in South Pasadena. The home carries captivating lore from its very first owner, a dentist who ran a clever Prohibition-era operation. Treating patients in the sunlit parlor served as the perfect front, while the backyard provided discreet access to his clandestine speakeasy upstairs. Now extensively remodeled while preserving its authentic historic frame, upgrades include a brand-new roof, dual-zone HVAC, and dual-pane tempered windows. A welcoming front porch leads into a formal living room anchored by preserved 1917 Philippine Mahogany colonnades and an inglenook fireplace with artisan tile. Double French doors reveal an impressive two-story foyer finished with Italian Carrara checkerboard marble floors and a cascading chandelier, opening into the bright historic parlor. The kitchen is appointed with Monet Garden Marble slab counters and backsplash, custom cabinetry, a prep island, and breakfast peninsula, along with a Sub-Zero refrigerator, 6-burner Wolf range with pot filler, and Cove dishwasher. A private main-floor wing features a designer bath with a floating Italian Calacatta Viola marble vanity, an en-suite multi-generational bedroom, and a 5th bedroom, both opening through sliding glass doors to the rear deck. Upstairs, the expansive primary suite rests beneath authentic 1917 exposed timber trusses from the speakeasy past. This private wing offers a sitting lounge, window daybed nook, open dressing room, two finished storage rooms, and a spa-inspired bath with Calacatta Viola marble, a deep soaking tub, and a frameless glass shower. Two additional bedrooms overlook the backyard tree canopy, one with a secret play nook under the roofline. Kohler collection fixtures are featured throughout. The flat, nearly 9,300-sqft grounds offer exceptional outdoor living with prime ADU potential. A raised deck with a retractable awning steps down to a geometric paver terrace, a lush lawn, and a mature shade tree. A long driveway with 220V 50-amp EV charging leads to the detached oversized garage with room for parking and a workshop or studio. Located in the sought-after South Pasadena school district with its middle and high schools just a 7-8 minute walk away, you are also moments from the Metro station and the vibrant weekly Farmers Market along historic Mission West. This home combines timeless character with modern livability.