Set on a rare 3-parcel, 0.43-acre lot, this one-of-a-kind Woodside property blends timeless character with modern updates in one of the areas most coveted neighborhoods. Surrounded by mature oaks and breathtaking foothill views, it offers the perfect balance of privacy, nature, and conveniencejust minutes from scenic trails, open space preserves, major freeways, and vibrant downtown Woodside. Originally built in the 1920s, the home exudes classic charm while showcasing thoughtful renovations, including a beautifully updated kitchen, fresh interior paint, and a versatile lower-level guest or bonus suite. Vaulted wood-beamed ceilings add warmth and character to the main living areas, complemented by a formal dining room and multiple flex-use rooms that can serve as offices, guest quarters, or creative spaces. On the first floor, you'll find a full bathroom, bonus living or guest area, plus a bonus room ideal for storage, a home workshop, or future expansion. With over 2,400 sq. ft. of living space, this flexible layout offers endless potential for customization and growth. Offering an exceptional opportunity, this property is perfect for builders, investors, or those dreaming of creating their own Woodside retreat.