Welcome to 592 Oakland Avenue, a charming single-family home nestled in the highly desirable Sunset Hill neighborhood, offering timeless character, generous living space, and thoughtful upgrades throughout. Enter inside and appreciate the home's classic details, including high ceilings, original hardwood floors, and beautiful chestnut trim. With more than 20 windows throughout, natural light fills the home, creating a bright and inviting atmosphere. The main level features a spacious living room, dining room, cozy den perfect for a home office, and an eat-in kitchen highlighted by a beautiful bay window. A rear door provides seamless access to the spacious deck and private backyard. The enclosed front porch offers additional versatile living space while helping maintain indoor comfort throughout the changing seasons. The home offers 3 bedrooms and 2 full bathrooms, including one with a convenient walk-in shower. The fully finished basement provides additional usable space, while the spacious finished attic is a rare and valuable feature for a home of this style. Complete with walk-in closets, the attic offers exceptional flexibility uses. Adding to the home's appeal are numerous upgrades and energy-efficient features, including a newly upgraded electrical panel, four energy-efficient ductless heating and cooling split systems (one in each bedroom and one on the main level), and a hot water heating system. Additional highlights include a roof with a lifetime warranty, specially insulated vinyl siding for improved energy efficiency, and a maintenance-free exterior. Abundant closets and storage throughout provide even more everyday convenience.