JAIME’S REAL ESTATE BRIEF How Your Generation Thinks About Real Estate

Jaime Hechtman Ulloa
Mar 23
4 min read

How Your Generation Thinks About Real Estate — And What It Means for You on Long Island

By Jaime Hechtman Ulloa

631.664.0268

I came across something recently about how each generation thinks differently - about money, work, life and it made me stop and think:

That mindset shows up very clearly in real estate.

Every day, I sit with buyers, sellers, families, and investors here on Long Island, and I can almost always tell how someone approaches real estate based on how they were raised, what they lived through, and what they believe about stability and risk.

The truth is, there’s no “right” way to think about real estate but understanding your mindset can completely change the decisions you make.

Baby Boomers: Built on Stability and Ownership

If you’re a Baby Boomer, real estate was never a question it was the plan. You bought early, stayed put, paid down your mortgage, and built wealth through your home. And that strategy worked. Today, homeowners in the U.S. hold over $35 trillion in home equity, making real estate the foundation of middle-class wealth. On Long Island, many of you are sitting on homes with significant value and you’ve earned it.

But here’s what I’m seeing now:

Many Boomers are staying put longer than ever, often because of low mortgage rates or taxes. That’s creating a ripple effect… fewer homes hitting the market, which impacts the next generation trying to buy.

At some point, though, transitions happen. Downsizing, relocating, or planning estates becomes part of the conversation. And when that shift happens, it opens doors for everyone else.

Gen X: The Quiet Decision-Makers

Gen X doesn’t always get talked about but you’re the backbone of today’s market. You’re raising families, managing careers, helping aging parents, and often supporting kids at the same time.

In real estate, that shows up as:

Upgrading homes
Downsizing strategically
Managing multi-generational living

You tend to be practical. You don’t chase trends you make moves when they make sense. And right now, Gen X is often the one coordinating the biggest decisions in a family:

Selling a parent’s home.

Helping a child buy their first.

Balancing everything in between.

Millennials: Redefining What Homeownership Looks Like

Millennials changed the game. You didn’t follow the traditional timeline and honestly, you couldn’t. Between student debt, rising prices, and a changing economy, buying a home got pushed later. In fact, the average first-time homebuyer age has climbed to around 40, a record high.

But here’s what’s interesting:

You didn’t give up on homeownership, you redefined it.

You’re:

Buying later, but more intentionally
Focused on lifestyle and flexibility
Open to condos, townhomes, and different setups
Highly aware of monthly payments and long-term value

And right now, Millennials make up one of the largest shares of buyers in the market, driving demand forward. On Long Island, I see this every day…buyers who are thoughtful, informed, and focused on building something meaningful, not just buying a house.

Gen Z: The Most Financially Aware Buyers Yet

Gen Z is just getting started but don’t underestimate them. Even with today’s challenges, about 27% of Gen Z already owns homes, and that number is growing.

This generation is:

Extremely research-driven
Open to investing earlier
Thinking about equity, not just lifestyle
Comfortable with creative strategies

They’re also realistic. They know the market isn’t easy but they’re still finding ways in. Some are living at home longer. Some are buying smaller. Some are investing before upgrading. But they’re paying attention, and that matters.

So What Does This Mean for Long Island Right Now?

Here’s where it all comes together. Right now, we have:

Older generations holding valuable homes
Middle generations making key transitions
Younger generations trying to enter the market

And that creates a very specific kind of market…one that is constantly shifting based on who is moving, who is waiting, and who is ready.

What I always tell my clients is this:

Real estate isn’t just about the market, it’s about your position in it. Because while every generation thinks differently, one thing hasn’t changed:

Owning property is still one of the most powerful ways to build long-term stability and wealth. Studies continue to show that homeownership increases overall wealth and financial security over time, making it one of the most consistent financial strategies across generations.

My Take as a Local Agent

On Long Island, timing matters; but understanding your situation matters more. If you’re waiting for the “perfect” moment, you may miss a good one. If you’re thinking about making a move, ask yourself: