Set on one of Windsor Square's most iconic tree-lined streets, 257 S Van Ness is a classic California two-story home that offers elegance, scale, and endless potential. With over 3,600 square feet of living space, 5 bedrooms, and 3 bathrooms, the home delivers a perfect layout layout that feels both generous and effortless. Updated over the years and well maintained, the interiors are welcoming and thoughtfully configured. With a formal entry leading into a traditional living room and dining room, the home creates a natural flow for gatherings and quiet moments alike. The kitchen is a standout - anchored by a central island, with ample counter space and a dining table making it both functional and spacious. Whether cooking casually or entertaining a crowd, it's the heart of the home. The family room off of the kitchen opens to the backyard with room for a pool and ADU. There is also a bedroom, office, flex room and a full bath on the first floor. Upstairs, there is a primary suite as well as two additional large bedrooms that share a bath. A surprising 800+ square foot flat roof deck is over the family room, ideal for expansion or a rooftop retreat. Set on an over 10,000 square foot lot, the property offers a large, private yard and a detached garage ready for transformation into a guesthouse. Located in the Third Street School district, this is a home that blends comfort, location, and square footage just blocks from the best of Larchmont Village. Live beautifully as is, or bring your vision to life - this is the kind of home that rarely comes to market.