Discover the perfect blend of location, character, and quality at 142 Shandwick Street, nestled at the end of a quiet dead-end street in Sydney’s desirable south end. Situated on a large, private treed lot just minutes from downtown, this stunning home offers peace, privacy, and beautiful natural surroundings—right next to the Green-Link trail, Cromarty Tennis Club and Wentworth Park Brook. This charming 2.5-storey home has been fully and respectfully renovated from top to bottom, transforming it into a warm, inviting family retreat while preserving its timeless character. Inside, you'll find original wood trim, gleaming hardwood floors, and thoughtfully designed spaces throughout. The main floor features a modern kitchen and dining area, a cozy half bath off the side entrance, and a spacious formal living room with a stone fireplace and pellet insert, accented by a rich oak mantle. A bright family room/study with original French doors adds a quiet retreat for reading or working. Step outside to a large patio deck—perfect for entertaining and taking in the serene views of the surrounding hardwoods. Upstairs, the second floor offers three comfortable bedrooms, including a primary suite with double closets and access to a covered 15' x 12' pergola balcony overlooking the valley below. The third floor provides a fourth bedroom plus additional office or storage space, ideal for a growing family or creative use. The bright and spacious walkout basement in-law suite includes one bedroom, a full bathroom, and its own entrance—perfect for extended family or as a potential income-generating rental unit.