Vansittart Avenue: Timeless Homes in the Heart of Woodstock

Stretching through the heart of Woodstock, Vansittart Avenue is one of the city’s most recognizable and sought-after streets - known for its blend of historic charm, mature trees, and elegant character homes. Lined with beautiful century residences, stately red-brick properties, and thoughtfully updated modern builds, the avenue captures the essence of Woodstock’s timeless appeal. Its central location offers convenient access to downtown shops, restaurants, and local parks, while maintaining a sense of peace and community that makes it a favourite among long-time residents and newcomers alike. Whether you’re drawn to its architectural beauty, walkable lifestyle, or welcoming neighbourhood feel, Vansittart Avenue continues to stand out as one of Woodstock’s most desirable places to call home.

105 Vansittart Avenue, Woodstock Ontario

Listed by Jay Friesen, Broker – The Jennifer Gale Team, Gale Group Realty Brokerage Ltd.

A landmark residence on one of Woodstock’s most prestigious streets, 105 Vansittart Avenue is a stunning century home that perfectly balances historic charm with modern comfort. With over 4,600 sq. ft. of living space, 7 bedrooms, and 3.5 bathrooms, this home has been lovingly cared for by only four families in more than 125 years. Original millwork, hardwood floors, and architectural details showcase its heritage, while thoughtful updates to the kitchen, plumbing, and electrical systems bring peace of mind for today’s lifestyle. Nestled among mature trees— including one of only two Dawn Redwoods in the city—this remarkable property is as rare as it is beautiful.
Check out the full listing to this beautiful home here.

155 Vansittart Avenue, Woodstock Ontario

Listed by Drew Symons, Sales Representatives – The Jennifer Gale Team, Gale Group Realty Brokerage Ltd.
Karli Hawes, Sales Representatives – The Jennifer Gale Team, Gale Group Realty Brokerage Ltd.

Set beside picturesque Vansittart Park, this elegant 2-storey century home combines timeless character with thoughtful modern updates. Featuring 4 bedrooms and 3 bathrooms, the home showcases original details like high ceilings, exposed brick, a pocket door, and a charming tin kitchen ceiling. Recent upgrades include new windows and doors (2024), refreshed paint throughout, updated electrical, and modern lighting, ensuring comfort and peace of mind. Outside, the property offers a fully fenced yard, newly redone back porch (2025), refinished upper balcony, and a spacious asphalt driveway leading to an oversized, insulated 2-car garage—perfect for a workshop or studio. With its unbeatable location and move-in-ready appeal, 155 Vansittart Avenue stands as another beautiful example of why this street remains one of Woodstock’s most desirable.
Check out the full listing to this beautiful home here.