Welcome to 164 Chestnut Hill Drive, a classic 1928 Old Style home filled with timeless charm, tucked on a quiet, tree-lined street in the heart of West Irondequoit! This impeccably maintained property sits on a deep 171-foot lot and offers nearly 2,000 sq ft of character-rich living space—just minutes from shopping, parks, restaurants, and the 104 expressway. Original gumwood trim, hardwood floors, and elegant arched doorways showcase the craftsmanship of the era. Enjoy a spacious living room with a wood-burning fireplace, formal dining room, sun-filled bonus room, and an eat-in kitchen with walk-in pantry. Upstairs offers three generous bedrooms, including a spacious primary with an attached bonus room—ideal for a home office, dressing area, or quiet retreat—plus a full bath with classic tilework and vintage character. A full walk-up attic provides excellent storage or potential expansion. Downstairs, the walkout basement adds rare flexibility with a second full bathroom, laundry area, and a full kitchen—perfect for in-law, guest, or multigenerational living, or simply extra space to enjoy yourself. Outside, the deep backyard offers space to garden, entertain, or simply unwind. The detached garage includes two vehicle bays plus a third flexible bay—ideal for storage, a workshop, or hobby space—with wood paneling and windows that bring in great natural light. This home is move-in ready and offers plenty of room to grow in a prime West Irondequoit location!