Step into timeless elegance at 99 Olive Street, a rare Queen Anne Victorian style three-family in the heart of Wooster Square! This striking brick home showcases the best of 19th-century craftsmanship, with its intricate detailing, patterned facade, and beautifully preserved historic character. This lovingly maintained, legal 3 family with a bonus office space, has been thoughtfully updated. The property features a newer roof, rebuilt chimney, updated mechanicals, and recent repointing of the whole brick exterior, preserving its beauty and ensuring long-term integrity! Inside, each spacious unit offers high ceilings, hardwood floors, fireplaces, and large windows that fill the rooms with natural light. Private backyard with garden boxes and community grill is great for entertaining and relaxing in the heart of the city. Separate utilities and flexible layouts make it ideal for both investors and owner-occupants. Enjoy everything Wooster Square has to offer right outside your door- the park, weekend farmers market, cafes, and the legendary Sally's and Pepe's Apizza. Just minutes to Yale, downtown, and Union Station, this home perfectly blends Queen Anne elegance with modern reliability and city convenience. A true Wooster Square gem, full of charm, character, and opportunity.