Welcome to 99 Hillcrest Avenue, a beautifully updated century home in the heart of highly sought-after Kirkendall South. Lovingly maintained and extensively updated, every improvement has been made with careful attention to detail, preserving the home's original character while enhancing comfort and functionality for today's lifestyle. The main level is designed with families in mind, featuring a powder room, spacious kitchen with adjoining breakfast and sitting area, as well as a formal dining room perfect for hosting family gatherings and special occasions. The second floor offers three bedrooms along with full bath and the convenience of bedroom level laundry, while the entire upper level is dedicated to a private primary retreat – a rare sanctuary complete with exceptional privacy and separation from the rest of the home. Outside, the professionally landscaped backyard is an entertainer's dream. Multiple seating and gathering areas, dedicated play space for children, and mature landscaping create a private outdoor oasis. Backing directly onto the greenspace, the property enjoys a unique connection to nature with exceptional privacy and immediate access to the Chedoke Trail, Dundurn stairs and much more. An attached garage/workshop and two-car driveway complete this outstanding offering. Recent updates provide peace of mind, including new windows, new furnace and AC (2026), and a durable metal roof, and much more. Rarely does a home combine the character, updates, location, and lifestyle that 99 Hillcrest offers. Set on one of Kirkendall South's most desirable streets, this is a truly special property where city living, and nature exist in perfect harmony.