Perched on a desirable uphill street in Highland Park, this classic California bungalow blends timeless character with thoughtful modern upgrades and layered outdoor living. This 2-bedroom, 1-bath home plus dedicated office sits on a 5,464-square-foot lot, offering rare space and versatility in one of the Eastside's most sought-after neighborhoods. The layout is efficient yet inviting, filled with natural light and anchored by light-oak toned floors that bring warmth to the living spaces. The renovated kitchen and bath, central HVAC, and newer roof provide comfort and peace of mind, while the separate office creates ideal flexibility for working from home or creative pursuits. A downstairs bonus space with a bathroom adds even more room for guests, a gym, or additional workspace. The backyard unfolds in intentional layers designed for entertaining and everyday enjoyment, a large patio for gatherings, a generous grass area, and then easing into a newly built outdoor kitchen complete with a Gozney pizza oven. Recent improvements include redwood decks, a pergola with overhead heat lamps and cafe lighting, new turf, and lush privacy hedging that create multiple spaces for relaxing and entertaining. The outdoor kitchen is outfitted with granite countertops, a Santa Maria-style grill, flat-top griddle, dual refrigerators, and ample prep and storage space. Lush landscaping, including mature citrus and fig trees plus a stately sycamore, completes the setting. Just moments from the vibrant shops, restaurants, and cafes nearby, this is an intentionally updated bungalow that captures the best of Highland Park living.