Along the most coveted stretch of Sierra Madre’s iconic Alegria Avenue lies a singular opportunity—an expansive dual-parcel property spanning over 21,000 square feet of flat, usable land, graced with mature citrus trees and framed by the tranquility of the San Gabriel foothills. With two distinct structures, each with its own address and private driveway, this rare compound is zoned as a legal triplex and offers unmatched versatility for investors, builders, or owner-occupants with vision. The primary residence at 185 E Alegria has been thoughtfully reimagined and underwent a full renovation around 2021. A custom kitchen with marble countertops, wide-plank wood floors, new windows, fresh interior and exterior paint, and central air create a refined yet comfortable living environment. A finished lower level adds additional bedrooms and flexible space for guests, creative work, or extended living. At 181 E Alegria, a separate guest house includes two generous one-bedroom suites—each renovated inside and out, with updated kitchens, baths, and light-filled interiors. The property’s current configuration allows for immediate rental income or a graceful multi-generational setup, while its size and zoning open the door for further design potential (buyer to verify). This is a property that invites both present-day enjoyment and long-term imagination. Whether restoring and enhancing the existing three units or crafting a visionary compound, the location—on one of Sierra Madre’s most desirable streets—offers enduring appeal, walkability to downtown, and a setting rich in character and history. There may be potential for subdivision, subject to city approval' buyer to verify all possibilities with the City of Sierra Madre. Rarely does a property offer this level of flexibility, scale, and charm in such a coveted location.