Kingston’s Past Present and Future real estate prices.

A Look at Kingston’s Past, Present, and What Really Makes a Home

As a real estate agent, I hear it all the time: “Should I buy now, or should I wait? Will prices go up or down?” If I had a crystal ball, believe me, I’d be a billionaire. Over 30 years in the Hudson Valley, I’ve seen the market rise, fall, and move sideways.

I’ve bought and sold

numerous properties, from single-family homes to multi-family buildings, even 1031 exchanges and fix-and-flips. Yet, no matter how much experience I have, the future is always uncertain.

While the ‘08 financial crisis was a massive global shock, not all seismic events get national headlines. In Kingston and Ulster County, we lived through a different, quieter earthquake: IBM’s departure. Nationally, that wasn’t front-page news, but locally, it was everything. I was here for both. When IBM pulled out in the early ’90s, it left a crater in our economy. It felt local, but it changed lives. It wasn’t until 2000, at the tail end of that IBM downturn, that I bought my first home in New Paltz for $90,000. I caught that transition firsthand. 

Fast forward to 2008, and I was no longer just a homeowner—I had six rental units and my own home. When that crisis hit, the PTSD is real to this day. Globally, everyone remembers 2008 as a financial catastrophe, but for me, it was personal—juggling tenants, mortgages, uncertainty. I’ve lived through both: one local crash that shaped our region, and one global crash that everyone felt. The lesson is this: just because something isn’t national news doesn’t mean it won’t shape your life. I’ve seen how hyper-local events can have lifelong impacts, even if they aren’t on everyone’s radar. So when we look at the future, remember: local and global events both matter. I’ve been through both, and that’s why, here, we pay attention to both.

Kingston, New York, and Ulster County are unique in that at certain times, nearly half of the homes were weekend homes. This close connection to New York City is both a blessing and a challenge. Whatever happens in the city often ripples up here. Historically, when the city struggles, we often see an upstate boost.

Think of the dot-com bust: when Wall Street felt shaky, interest rates dropped, and money flowed into real estate. After 9/11, when the city felt unsafe, people sought the Hudson Valley: affordable, beautiful, yet close. The pandemic? No one foresaw the city exodus, but it happened, driving more interest here.

Now, with future uncertainties—wars, potential property tax hikes in the city—do we know what’s next? No. And if any agent claims they do, run! But one pattern is clear: what’s bad for NYC often becomes good for us. Use that insight not as a forecast, but as a perspective. Decide when or what to buy based on your own needs. And remember—renting’s always an option too.

But here’s the other truth about Kingston’s Past Present and future real estate prices, a home isn’t just an investment. Sure, it’s where a lot of your money goes, but it’s also where life happens. If we only chased “best investments,” we’d all cram into multi-family units and skip the joy of a home. A home is where you raise a family, where you play, where you find stability. Yes, real estate can build wealth over time, but if you’re only thinking short-term returns, you’ll miss the bigger picture: home is your foundation. So, think long-term. Think of the life you want to build—and I’ll be here to help you understand what’s right for you, right here in the Hudson Valley.