Location: Kingston, Ontario
Client Type: Upsizing Homeowners + Investors
Timeline: Offer to close: 2 months

The Challenge

A repeat client came to our team ready for their next step, both personally and financially. They owned a small wartime home in downtown Kingston, purchased years earlier through our team. With a growing family and a child starting school in the East End, space was getting tight.

At the same time, they were hoping to keep their existing property as a rental and maintain their Airbnb investment. The challenge? Financing three properties under one household budget, all while navigating new and changing short-term rental regulations.

Our Approach

Because this was a returning client, Lindsay was able to step in with an established level of trust and familiarity. Creating a smooth, open, and collaborative process from the start.

The search began over a year earlier, exploring everything from rural properties to homes in Clydesville and Seeley's Bay, before narrowing the focus to Kingston’s East End to stay close to the family’s daycare and school community.

Once the right detached home appeared (complete with a pool and the potential to renovate), Lindsay guided the clients through the complexities of financing while connecting them with key professionals to make the purchase possible.

With support from the team’s preferred mortgage broker, Lindsay helped the clients strategize how to structure their finances. Ensuring both their Airbnb and new rental property could remain sustainable. She also leveraged her background in property management to connect them with a trusted company that secured the exact rental rate needed to finalize financing for their upsize.

Through constant communication, creative problem-solving, and well-timed professional connections, the family was able to purchase their dream East End home without sacrificing their existing investments.

The Results

Timeline: November offer → January close
Outcome: Secured a detached East End home while retaining both existing investment properties

The clients successfully grew both their family home and their property portfolio — keeping their downtown home as a rental, maintaining their Airbnb, and moving into a home with room to grow (and space for a new baby on the way).

Key Takeaway

When goals involve both lifestyle and long-term investment, the right support network makes all the difference. By connecting clients with trusted mortgage and property management professionals and staying proactive through every stage of the process. Lindsay helped make an ambitious move both possible and stress-free.