Gracefully positioned on one of Picton's most picturesque, tree-lined streets, this exceptional century residence pairs enduring craftsmanship with thoughtful modern comfort. Offering over 4,000 square feet of living space with four plus two bedrooms and five bathrooms, this exceptional property seamlessly blends historic character with modern comfort. Just steps from Picton Main Street's vibrant shops, cafés, restaurants, and galleries, you'll enjoy walkable convenience without sacrificing peace and privacy. Enter through the impressive 24-foot sunroom into a welcoming foyer showcasing gleaming hardwood floors and exquisite period trim. The spacious formal living room sets the tone, while the heart of the home is the light-filled modern kitchen, complete with quality custom cabinetry. A gracious formal dining room with original hardwood floors and plate rails provides an ideal setting for entertaining, and the expansive family room offers a warm, inviting space for everyday living. Up the ornate staircase, two bedrooms each feature their own en-suite, creating serene private retreats. A separate self-contained suite with two additional bedrooms adds valuable flexibility-perfect for guests, extended family, or potential rental income. The finished basement includes another 2 bedrooms with a 7 x 12 generous walk-in closet, office space, laundry room and workshop/storage area. Outdoors, an exceptional two storey coach house and a private garden sanctuary await with easy-care perennial plantings and a stone patio ideal for alfresco dining. Whether you're seeking a refined private residence or a home that offers versatility and income potential, this remarkable property delivers the best of both worlds.