In the heart of Naglee Park, San Jose's cherished, historic neighborhood known for its strong community and architectural reverence, this 1906 Craftsman offers nearly 2,000 sf of timeless charm. A classic front porch with cedar shingle siding and clinker brick columns welcomes you into a home full of character with a bespoke Inglenook and fireplace seating, craftsman wainscot and molding, hardwood floors, and vintage doors and hardware. Thoughtful updates provide modern comfort with remodeled kitchen, baths, and laundry. The chefs kitchen boasts Wolf range, Viking double ovens, Thermador refrigerator, Miele dishwasher, and a large island with prep sink and breakfast bar. The layout flows from living and dining rooms to a spacious redwood deck, picnic table, arbor with benches, and low-water native landscaping shaded by mature trees and wisteria. The primary suite includes a redesigned en-suite bath, walk-in closet, and built-in bookshelf with storage bench. Two additional bedrooms share a remodeled hall bath. A detached oversized two-car garage with plumbing rough-ins invites ADU conversion. Solar (NEM 2.0) with battery backup, new high-efficiency heat pump, warrantied roof, and indoor/outdoor speakers complete this seamless blend of historic charm and modern functionality.