Rare 1917 Transitional Craftsman with stunning renovations, set 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 gave discreet access to his clandestine speakeasy upstairs. Extensively remodeled and newly finished while preserving its character-defining Craftsman woodwork, this unique historic property offers the pristine feel of a new home. Major upgrades include a new roof, dual-zone HVAC, and dual-pane tempered windows. A welcoming front porch leads into a formal living room anchored by 1917 Philippine Mahogany colonnades and an inglenook fireplace with artisan tile. Double French doors reveal an impressive two-story foyer featuring Italian Carrara checkerboard marble and a cascading chandelier, opening into the bright historic parlor. The kitchen is appointed with Monet Garden Marble counters and backsplash, custom cabinetry, a prep island, and breakfast peninsula, along with 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 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, deep soaking tub, and frameless glass shower. Two additional bedrooms overlook the 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 50amp EV charging leads to the detached oversized garage with workshop/studio space. Located in the sought-after South Pasadena school district with middle and high schools just 7-8 min walk away, you are moments from Garfield Park, local cafes, and the vibrant weekly South Pasadena Farmers Market. This home combines timeless character with modern livability.