Built circa 1916, this distinguished Four Square Shingle-Style Colonial has been reimagined for modern living while preserving the timeless craftsmanship and character of its era. Set on a quiet, tree-lined stretch of a coveted downtown street, the home offers the rare combination of serenity and city convenience-just one mile to the Stamford train station & minutes to downtowns vibrant shops, dining, & nightlife. Step inside to discover exquisite period details at every turn: rich oak, mahogany, & pine millwork; a detailed brick fireplace; custom built-ins; wainscoting; coffered 9ft ceilings; & original stained-glass windows that cast warm, colorful light throughout the home. With 5 bedrooms & 3 full baths, the flexible layout includes a private third-floor suite-ideal for guests, nanny, or extended family. Built by the family who owned The Stamford Lumber Company, the home has been lovingly cared for & thoughtfully updated with a timeless kitchen featuring new appliances, thoughtfully renovated baths, and updated systems. A gracious wraparound porch invites relaxation & connection-perfect for morning coffee, evening cocktails, or gatherings with friends. Mature specimen plantings surround the home, creating a sense of privacy & calm. Perched above the city with tree top privacy, a stone patio, level lawn oversized 2 car garage on Valley Road, this residence embodies the perfect blend of architectural heritage, comfort & sophistication.