Set on a coveted street in Kenilworth, this impeccably maintained home pairs timeless architecture with an exceptionally rare floor plan featuring six bedrooms, including five on the second level. Thoughtfully expanded and extensively renovated, the home blends classic detailing with a tailored, city-chic aesthetic across every level. A gracious foyer introduces dramatic entertaining spaces including a striking living room with fireplace and an elegant formal dining room. The butler's pantry connects seamlessly to the custom kitchen, featuring high-end appliances, oversized island seating, and clean-lined finishes, all overlooking the expansive professionally landscaped grounds. The sought-after open floor plan flows effortlessly through the breakfast area and into the family room, creating a polished yet highly functional living space. A private first-floor office with custom built-ins is discreetly tucked away. Additional functional spaces include a spacious mudroom, first-floor laundry, and attached two-car garage. The second level features five bedrooms, including a stunning primary suite with two walk-in closets and a luxe bath with walk-in shower, soaking tub, and dual vanities. One secondary bedroom includes an ensuite bath and walk-in closet, while three additional bedrooms share a well-designed double Jack-and-Jill bath arrangement. The show stopping third-floor addition introduces over 1,200 square feet of architecturally significant living space with sweeping ceiling heights and a distinctly loft-inspired, city-chic sensibility. The level includes a recreation room with kitchenette, exercise studio with reinforced soundproof flooring, full bath, and additional bedroom or flex space. The lower level continues the home's impressive scale with a large recreation room, wet bar, second laundry room, and exceptional storage. Professionally landscaped grounds extend the living space outdoors with a sport court, bluestone terrace, built-in outdoor kitchen, custom firepit, and multiple entertaining areas integrated throughout the property. The thoughtfully executed renovation and expansion by Chip Hackley Architects includes the third-floor addition, new primary suite, mudroom and first-floor laundry, bluestone patio, outdoor kitchen, sport court, window replacement throughout, updated electrical and plumbing systems, and renovated lower level. Throughout, the home reflects a rare combination of architectural integrity, modern functionality, and polished design in one of the North Shore's most sought-after communities.