"From One Traveler's Dream to Millions in Managed Homes”

Our Journey:

In the bustling streets of Toronto in 2015, a story began with an entrepreneur's leap from the corporate world into the exhilarating realm of travel. After leaving a structured corporate career, our founder stumbled upon Airbnb — first as a way to monetize his vacant apartment while globetrotting, and soon, as an indispensable part of his own journeys. This dual perspective of being both a traveler and a host provided him invaluable insights into the ever-evolving landscape of short-term rentals. The charm of experiencing diverse cultures from the comfort of someone's home was an idea that captivated him.

Yet, as he explored this new terrain, he noticed gaps. Despite the convenience offered, there lacked a bridge between the conventional understanding of residential management and the dynamic world of short-term rentals. The market was missing a touch of professionalism and a consistent level of service. Recognizing this void, he envisioned a company that could seamlessly integrate these two worlds, delivering the best of both to homeowners and travelers.

Bringing this vision to life required expertise. Gathering a team of skilled designers, adept tradespeople, and forward-thinking entrepreneurs, The Kressley Group was born. Our mission was clear from the beginning: to ensure that buildings under our management not only met the standards of short-term rentals but thrived as harmonious communities. This meant redefining how guests and residents experienced their stay, ensuring every interaction was seamless, memorable, and world-class.

Our unique approach didn't go unnoticed. Property developers, builders, and investors soon recognized the potential and synergy we offered. They saw in us not just a property management firm, but a partner that understood the intricacies of both hospitality and property management. This opened doors to collaborations on diverse projects, ranging from boutique hotel properties to upscale residential complexes.

As we dived deeper, we realized the symbiotic relationship between managing exquisite short-term rentals and residential properties. The meticulous attention to detail, the commitment to unparalleled service, and the continuous drive to create memorable experiences for guests were all skills transferable to residential property management. It was an epiphany. Why couldn't the ethos of hospitality be integrated into the very fabric of residential management?

Thus began our journey of redefining residential property management. With a renewed purpose, we set forth to elevate everyday living experiences. By infusing the art of service and hospitality into our management approach, we aimed to enhance the value for both landlords and tenants. No longer was property management just about brick and mortar. For The Kressley Group, it was about creating experiences, forging connections, and building communities.

Today, The Kressley Group stands as a testament to that vision, proudly managing tens of millions in property assets. As we look back at our humble beginnings, we are filled with gratitude for the journey and the countless partners, homeowners, and guests who have trusted us. Our commitment remains unwavering: to bring the finest elements of hospitality to the world of residential property management, ensuring every home feels like a curated escape and every stay becomes a cherished memory.