Set on an expansive, flat 8,551 sq ft lot in Highland Park’s most desirable pocket, this thoughtfully updated California bungalow compound features a spacious and private 2 bed, 1 bath main residence and a detached 1 bed, 1 bath guest house. The turnkey property offers seamless indoor/outdoor living, with a breathtaking outdoor space featuring a flat grassy yard, dining area, garden beds, and a built-in cowboy pool off the back deck. Located north of York Boulevard, just blocks from Occidental College and Fiji Hill hiking trail, on a wide tree-lined street, the idyllic setting offers privacy, timeless design, and the best of Highland Park living. Enter the main residence to find a tastefully refreshed, romantic home with hardwood floors throughout, newly painted interiors, and curated lighting that elevates each space. Upon entry, find the foyer centered on an elegant, vintage brick fireplace, flanked by the dining area. The adjacent kitchen features quartz countertops with bar seating, refinished cabinetry, white porcelain backsplash tile, and new Zia cement tile flooring, with a dedicated laundry area at the far end. Two bedrooms at the front of the home face the grassy yard. The recently renovated bathroom is a standout, finished in a custom tonal pink palette with Sahara matte porcelain tile and hexagon flooring by Bedrosians, a frameless glass walk-in shower, and an enlarged window that fills the space with natural light. Through the den, find a fully reimagined backyard with a mix of lush lawn and pea-gravel gathering areas, mature ficus and Palo Verde trees, and winding paver and flagstone pathways connecting each section of the lot into distinct spaces for lounging, dining, and entertaining. From the center yard, windowed French doors open to the 1 bedroom, 1 bathroom guest house, a stunning detached structure that adds 570 square feet. Inside, the main living space is generously sized, offering flexibility for a studio or home office. A vintage wood door with hand-painted glass opens to the back bedroom, with striking wood-vaulted ceilings and wood-framed doors and windows overlooking a verdant additional backyard. Off the back bedroom, a private garden retreat awaits, complete with a deck with a cowboy tub and an additional outdoor dining area. Mature trees, anchored by a hammock, shade the property and are surrounded by ample space for raised beds, fruit trees, or a small orchard, designed with the home gardener in mind. Significant system upgrades throughout the property include a fully replaced trenchless sewer lateral, upgraded irrigation with new lines and controls, French drains around the guest house, and a recently serviced tankless water heater, providing both comfort and peace of mind. Ideally located just moments from the energy of York Boulevard, the home is surrounded by some of Highland Park’s most beloved destinations, including Joy, Belle’s Delicatessen, Kumquat Coffee, and Johnny’s Cocktails. With one of the neighborhood’s larger and more versatile lots, beautifully updated interiors, and exceptional outdoor spaces, this Highland Park retreat offers a rare opportunity to experience elevated Eastside living.