Set among the pines on two expansive lots, this remarkable 1970s Mid-Century mountain retreat offers a rare opportunity to own a private Lake Arrowhead compound where timeless architecture, nature, and versatility come together. Two distinct residences are connected by generous entertaining decks and abundant outdoor living space, creating a seamless setting for quiet escapes, lively gatherings, and effortless indoor-outdoor living, framed by sweeping mountain views and a serene forest backdrop. The 4-bedroom, 2-bath main residence showcases classic Mid-Century design with soaring vaulted ceilings, exposed beams, knotty pine throughout, walls of windows, and an iconic freestanding wood-burning fireplace. The flexible floor plan includes a main-level bedroom and full bath, currently serving as a media room, a lofted bedroom, and two lower-level bedrooms, including a primary suite with an en-suite bath. Both lower-level bedrooms enjoy direct outdoor access. Multiple decks extend the living spaces outdoors, while updates include a rebuilt deck, hardwood laminate flooring throughout the main level, an upgraded electrical panel and outlets, central air conditioning, a mini-split system, a 10kW backup generator, and abundant storage. The detached spacious guest house embraces its own distinctive Mid-Century character with a dramatic stone fireplace, iconic sunken conversation pit, and spectacular indoor hot tub. Surrounded by towering pines, this private retreat features a rebuilt deck, mini-split heating and cooling, luxury vinyl plank flooring, and a paved asphalt driveway. Currently operating as an active Airbnb, it offers exceptional flexibility as an income-producing rental, guest accommodations, or a private escape. Centrally located in a well-established Lake Arrowhead neighborhood, this property is minutes from Lake Arrowhead Village, the Country Club, and the lake. Ownership includes coveted Lake Rights, while nearby forest trails, shopping, and dining are just moments away. With abundant parking, including space for a boat, exceptional privacy, multiple living opportunities, and iconic Mid-Century architecture, this is a truly rare offering where mountain living and timeless design come together. Best access to the property is via 394 Rainer Road.