A rare compound with three homes set across one expansive lot, currently configured as four distinct living spaces, offering flexibility, privacy, and layered architectural character. This curated property spans multiple residences, each with its own distinct identity while remaining connected through a shared sense of character. From the reimagined 1901 Craftsman to the restored 1918 main home and guest residences, the property offers a layered experience designed to support a range of lifestyles. Ideally located in Ocean Park just moments from the beach and Main Street. 2116 | The 1901 Cottage Craftsman has been carefully reworked, blending historic character with refined, design-forward living. A double-height living room with vaulted ceilings, skylights, and hand-stained beams creates a dramatic sense of volume, while original brick, leaded glass windows, and white oak flooring ground the space. The kitchen showcases exceptional craftsmanship with Cristallo quartzite countertops, a backlit island, custom Amish-built cabinetry, and a La Cornue range with Thermador appliances. A spiral staircase connects to a loft above, and a lower level featuring a secondary living area, wine bar with 250-bottle storage, and a flexible studio with kitchenette and bath. 2116 1/2 | The 1916 Craftsman back house offers a more intimate, character rich living environment. Original hardwood floors, wainscoting, a stone fireplace, and a vaulted beam ceiling define the living space, while a cottage-style kitchen opens to outdoor entertaining. Two bedrooms and one bath, including a clawfoot tub, are complemented by a 500 sq ft basement bonus space. Privately positioned, it works well for guest use or rental income. 2118 | The 1923 residence introduces a more expressive, globally influenced design. Moroccan plaster, custom ironwork, and curated finishes define the interiors, anchored by a gas fireplace and white oak and marble flooring. The kitchen features Fantasy quartzite, Samsung appliances, wine storage, and hidden detailing. Two bedrooms and 2.5 baths are thoughtfully arranged across levels, with the lower level offering additional lounge space and a custom powder room with unique design elements. 2118 1/2 | A fully independent residence below 2118, offering a bright, open layout with wood beam ceilings, a Carrara marble fireplace, and lime-washed brick accents. The kitchen features butcher block counters, a farmhouse sink, vintage appliances, and a retro refrigerator. With its own entrance, this unit is ideal for guests, rental income, or a private workspace. The landscaped grounds feature mature trees and layered plantings, including olive, citrus, fig, pomegranate, and mulberry. Grape vines and flowering gardens create a lush setting, while multiple outdoor entertaining areas and a DG/turf driveway provide both function and charm. Original outbuildings once horse stables remain on the property, along with a preserved French equestrian plaque, offering a subtle but meaningful connection to its past. Ideally located in the heart of Ocean Park, just moments from the beach and along the vibrant Main Street corridor, the property is surrounded by some of Santa Monica's most sought-after dining, cafes, and neighborhood favorites. From locally loved staples like Holy Guacamole to standout destinations such as Kobe's and Pasjoli, the area offers a dynamic and evolving culinary scene, including Michelin-recognized dining nearby. Everyday living is equally effortless, with the beloved Main Street Farmers Market, trending spots like Main Squeeze, and convenient access to neighborhood markets including Trader Joe's, Whole Foods Market, and Co+opportunity Market known for its organic and locally sourced offerings all just minutes away.