Interview with the Boss of Last Key Realty

I recently had the privilege to sit down and interview the Founder and Owner of Last Key Realty, Chris Santry, who also happens to be my boss. The purpose of this interview was to inform curious minds of the current overall state of the Key West Real Estate and Vacation Rental markets, as well as what the future holds for these markets and for our company.


Q: How has the Key West Vacation Rental Market changed since the start of Last Key Realty?

A: “When we first started in 2008, the “off-season” was truly an OFF-season. It used to be that a person could actually walk down the middle of Duval Street in Old Town without worrying about being hit by a car. Today, there is basically no “off-season”, with many summer weeks being completely sold out. And I’ve also seen the Key West Vacation Rental Market grow into a much more upscale vacation destination in recent years.”

Q: Where do you see the Key West Vacation Rental Market going?

A: “I see this upscale movement that was started by baby boomers continuing. As boomers are aging, younger generations who have discovered Key West are starting to take their place.”

Q: How was the Key West Real Estate Investment Market changed since the start of Last Key Realty?

A: “In just the ten years since Last Key Realty was founded, we have seen the investment real estate market virtually disappear and then return back to full strength. Presently, you have two groups competing: the people who are looking to purchase their dream or retirement home and reside in Key West, and the other group looking to invest in Vacation Rental property. This makes for an extremely vibrant real estate market. Thankfully many of the factors that attributed to the market crash a few years ago, like factoring of mortgages, no longer exist. We have a much more conservative banking system in place and there is also a much higher percentage of cash deals being made.”

Q: What is your future vision for Last Key Realty?

A: “My future vision for Last Key is controlled growth. It is essential to continue doing the same things that got us where we are today. Most importantly solid staffing, it is essential that we have committed and passionate people.”

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